TWI391424B - A hardened resin composition for inkjet and a hardened product thereof, and a printed circuit board using the same - Google Patents
A hardened resin composition for inkjet and a hardened product thereof, and a printed circuit board using the same Download PDFInfo
- Publication number
- TWI391424B TWI391424B TW95101064A TW95101064A TWI391424B TW I391424 B TWI391424 B TW I391424B TW 95101064 A TW95101064 A TW 95101064A TW 95101064 A TW95101064 A TW 95101064A TW I391424 B TWI391424 B TW I391424B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin composition
- inkjet
- curable resin
- mass
- compound
- Prior art date
Links
- 239000011342 resin composition Substances 0.000 title claims abstract description 32
- -1 bismaleimide compound Chemical class 0.000 claims abstract description 32
- 239000003085 diluting agent Substances 0.000 claims abstract description 21
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 11
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 10
- 125000003118 aryl group Chemical group 0.000 claims abstract description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 10
- 229920003192 poly(bis maleimide) Polymers 0.000 claims abstract description 8
- 150000001875 compounds Chemical class 0.000 claims description 29
- 239000011248 coating agent Substances 0.000 claims description 24
- 238000000576 coating method Methods 0.000 claims description 24
- 239000000203 mixture Substances 0.000 claims description 22
- 229910000679 solder Inorganic materials 0.000 claims description 20
- 239000000178 monomer Substances 0.000 claims description 13
- 239000003960 organic solvent Substances 0.000 claims description 8
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical group C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 3
- 238000001723 curing Methods 0.000 claims description 2
- 238000000016 photochemical curing Methods 0.000 claims 1
- 238000001029 thermal curing Methods 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 30
- 239000000047 product Substances 0.000 description 12
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 7
- 229920002120 photoresistant polymer Polymers 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000007747 plating Methods 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 5
- 229910052737 gold Inorganic materials 0.000 description 5
- 239000010931 gold Substances 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000007870 radical polymerization initiator Substances 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 4
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 4
- 244000028419 Styrax benzoin Species 0.000 description 4
- 235000000126 Styrax benzoin Nutrition 0.000 description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 description 4
- 229960002130 benzoin Drugs 0.000 description 4
- 238000013329 compounding Methods 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 239000003822 epoxy resin Substances 0.000 description 4
- 235000019382 gum benzoic Nutrition 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000647 polyepoxide Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000003513 alkali Substances 0.000 description 3
- 239000011889 copper foil Substances 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 230000005484 gravity Effects 0.000 description 3
- 150000002576 ketones Chemical class 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
- XQUPVDVFXZDTLT-UHFFFAOYSA-N 1-[4-[[4-(2,5-dioxopyrrol-1-yl)phenyl]methyl]phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C(C=C1)=CC=C1CC1=CC=C(N2C(C=CC2=O)=O)C=C1 XQUPVDVFXZDTLT-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
- BHNHHSOHWZKFOX-UHFFFAOYSA-N 2-methyl-1H-indole Chemical compound C1=CC=C2NC(C)=CC2=C1 BHNHHSOHWZKFOX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 229920000877 Melamine resin Polymers 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 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
- 230000000740 bleeding effect Effects 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- DIOQZVSQGTUSAI-UHFFFAOYSA-N decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 229910052747 lanthanoid Inorganic materials 0.000 description 2
- 150000002602 lanthanoids Chemical class 0.000 description 2
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 229910052759 nickel Inorganic materials 0.000 description 2
- 150000002978 peroxides Chemical class 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- UOHMMEJUHBCKEE-UHFFFAOYSA-N prehnitene Chemical compound CC1=CC=C(C)C(C)=C1C UOHMMEJUHBCKEE-UHFFFAOYSA-N 0.000 description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 description 2
- 150000003254 radicals Chemical class 0.000 description 2
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- DTGKSKDOIYIVQL-WEDXCCLWSA-N (+)-borneol Chemical group C1C[C@@]2(C)[C@@H](O)C[C@@H]1C2(C)C DTGKSKDOIYIVQL-WEDXCCLWSA-N 0.000 description 1
- KNXAMURPSBLVRZ-UHFFFAOYSA-N (decylamino)methanol Chemical compound CCCCCCCCCCNCO KNXAMURPSBLVRZ-UHFFFAOYSA-N 0.000 description 1
- XKSUVRWJZCEYQQ-UHFFFAOYSA-N 1,1-dimethoxyethylbenzene Chemical compound COC(C)(OC)C1=CC=CC=C1 XKSUVRWJZCEYQQ-UHFFFAOYSA-N 0.000 description 1
- ROLAGNYPWIVYTG-UHFFFAOYSA-N 1,2-bis(4-methoxyphenyl)ethanamine;hydrochloride Chemical compound Cl.C1=CC(OC)=CC=C1CC(N)C1=CC=C(OC)C=C1 ROLAGNYPWIVYTG-UHFFFAOYSA-N 0.000 description 1
- QWQFVUQPHUKAMY-UHFFFAOYSA-N 1,2-diphenyl-2-propoxyethanone Chemical compound C=1C=CC=CC=1C(OCCC)C(=O)C1=CC=CC=C1 QWQFVUQPHUKAMY-UHFFFAOYSA-N 0.000 description 1
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical compound NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 1
- KOMNUTZXSVSERR-UHFFFAOYSA-N 1,3,5-tris(prop-2-enyl)-1,3,5-triazinane-2,4,6-trione Chemical compound C=CCN1C(=O)N(CC=C)C(=O)N(CC=C)C1=O KOMNUTZXSVSERR-UHFFFAOYSA-N 0.000 description 1
- UNMYKPSSIFZORM-UHFFFAOYSA-N 1-(2-ethenoxyethoxy)butane Chemical class CCCCOCCOC=C UNMYKPSSIFZORM-UHFFFAOYSA-N 0.000 description 1
- SQZCAOHYQSOZCE-UHFFFAOYSA-N 1-(diaminomethylidene)-2-(2-methylphenyl)guanidine Chemical compound CC1=CC=CC=C1N=C(N)N=C(N)N SQZCAOHYQSOZCE-UHFFFAOYSA-N 0.000 description 1
- RJTJPFYIGZWFMK-UHFFFAOYSA-N 1-[2-(2-ethenoxyethoxy)ethoxy]-2-methoxyethane Chemical compound COCCOCCOCCOC=C RJTJPFYIGZWFMK-UHFFFAOYSA-N 0.000 description 1
- IPJGAEWUPXWFPL-UHFFFAOYSA-N 1-[3-(2,5-dioxopyrrol-1-yl)phenyl]pyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC(N2C(C=CC2=O)=O)=C1 IPJGAEWUPXWFPL-UHFFFAOYSA-N 0.000 description 1
- QZOPRMWFYVGPAI-UHFFFAOYSA-N 1-chloroindole Chemical compound C1=CC=C2N(Cl)C=CC2=C1 QZOPRMWFYVGPAI-UHFFFAOYSA-N 0.000 description 1
- OZCMOJQQLBXBKI-UHFFFAOYSA-N 1-ethenoxy-2-methylpropane Chemical compound CC(C)COC=C OZCMOJQQLBXBKI-UHFFFAOYSA-N 0.000 description 1
- QIUCYKBVFAPWRR-UHFFFAOYSA-N 1-ethenoxy-3-methylbutane Chemical compound CC(C)CCOC=C QIUCYKBVFAPWRR-UHFFFAOYSA-N 0.000 description 1
- IOSXLUZXMXORMX-UHFFFAOYSA-N 1-ethenoxypentane Chemical compound CCCCCOC=C IOSXLUZXMXORMX-UHFFFAOYSA-N 0.000 description 1
- ZIKLJUUTSQYGQI-UHFFFAOYSA-N 1-ethoxy-2-(2-ethoxypropoxy)propane Chemical compound CCOCC(C)OCC(C)OCC ZIKLJUUTSQYGQI-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- CERJZAHSUZVMCH-UHFFFAOYSA-N 2,2-dichloro-1-phenylethanone Chemical compound ClC(Cl)C(=O)C1=CC=CC=C1 CERJZAHSUZVMCH-UHFFFAOYSA-N 0.000 description 1
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 1
- BRKORVYTKKLNKX-UHFFFAOYSA-N 2,4-di(propan-2-yl)thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC(C(C)C)=C3SC2=C1 BRKORVYTKKLNKX-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
- OAYXUHPQHDHDDZ-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethanol Chemical compound CCCCOCCOCCO OAYXUHPQHDHDDZ-UHFFFAOYSA-N 0.000 description 1
- VXQBJTKSVGFQOL-UHFFFAOYSA-N 2-(2-butoxyethoxy)ethyl acetate Chemical compound CCCCOCCOCCOC(C)=O VXQBJTKSVGFQOL-UHFFFAOYSA-N 0.000 description 1
- FPZWZCWUIYYYBU-UHFFFAOYSA-N 2-(2-ethoxyethoxy)ethyl acetate Chemical compound CCOCCOCCOC(C)=O FPZWZCWUIYYYBU-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- DRLRGHZJOQGQEC-UHFFFAOYSA-N 2-(2-methoxypropoxy)propyl acetate Chemical compound COC(C)COC(C)COC(C)=O DRLRGHZJOQGQEC-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- MCNPOZMLKGDJGP-QPJJXVBHSA-N 2-[(e)-2-(4-methoxyphenyl)ethenyl]-4,6-bis(trichloromethyl)-1,3,5-triazine Chemical compound C1=CC(OC)=CC=C1\C=C\C1=NC(C(Cl)(Cl)Cl)=NC(C(Cl)(Cl)Cl)=N1 MCNPOZMLKGDJGP-QPJJXVBHSA-N 0.000 description 1
- WAEVWDZKMBQDEJ-UHFFFAOYSA-N 2-[2-(2-methoxypropoxy)propoxy]propan-1-ol Chemical compound COC(C)COC(C)COC(C)CO WAEVWDZKMBQDEJ-UHFFFAOYSA-N 0.000 description 1
- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 1
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- SBYMUDUGTIKLCR-UHFFFAOYSA-N 2-chloroethenylbenzene Chemical compound ClC=CC1=CC=CC=C1 SBYMUDUGTIKLCR-UHFFFAOYSA-N 0.000 description 1
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 1
- PGYJSURPYAAOMM-UHFFFAOYSA-N 2-ethenoxy-2-methylpropane Chemical compound CC(C)(C)OC=C PGYJSURPYAAOMM-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- KLAMVBJBHNQYSB-UHFFFAOYSA-N 2-ethyl-1-phenylbutan-1-one Chemical class CCC(CC)C(=O)C1=CC=CC=C1 KLAMVBJBHNQYSB-UHFFFAOYSA-N 0.000 description 1
- BWNBLGQCCSCCHF-UHFFFAOYSA-N 2-ethyl-1h-indole Chemical compound C1=CC=C2NC(CC)=CC2=C1 BWNBLGQCCSCCHF-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 1
- WVPGIDWFLXGCLA-UHFFFAOYSA-N 2-tert-butyl-1h-indole Chemical compound C1=CC=C2NC(C(C)(C)C)=CC2=C1 WVPGIDWFLXGCLA-UHFFFAOYSA-N 0.000 description 1
- QCAHUFWKIQLBNB-UHFFFAOYSA-N 3-(3-methoxypropoxy)propan-1-ol Chemical compound COCCCOCCCO QCAHUFWKIQLBNB-UHFFFAOYSA-N 0.000 description 1
- ARXVXVOLXMVYIT-UHFFFAOYSA-N 3-methylbutyl 2-(dimethylamino)benzoate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1N(C)C ARXVXVOLXMVYIT-UHFFFAOYSA-N 0.000 description 1
- VVBLNCFGVYUYGU-UHFFFAOYSA-N 4,4'-Bis(dimethylamino)benzophenone Chemical compound C1=CC(N(C)C)=CC=C1C(=O)C1=CC=C(N(C)C)C=C1 VVBLNCFGVYUYGU-UHFFFAOYSA-N 0.000 description 1
- LYIQTCFBZCGPLD-UHFFFAOYSA-N 4-[2-[5-(trichloromethyl)-1,3,4-oxadiazol-2-yl]ethenyl]benzonitrile Chemical compound O1C(C(Cl)(Cl)Cl)=NN=C1C=CC1=CC=C(C#N)C=C1 LYIQTCFBZCGPLD-UHFFFAOYSA-N 0.000 description 1
- YKXAYLPDMSGWEV-UHFFFAOYSA-N 4-hydroxybutyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCO YKXAYLPDMSGWEV-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- MRABAEUHTLLEML-UHFFFAOYSA-N Butyl lactate Chemical compound CCCCOC(=O)C(C)O MRABAEUHTLLEML-UHFFFAOYSA-N 0.000 description 1
- HRWNLDDLPMZDPP-UHFFFAOYSA-N CC1=C(C=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC(=CC(=C1)C)C Chemical compound CC1=C(C=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.CC1=CC(=CC(=C1)C)C HRWNLDDLPMZDPP-UHFFFAOYSA-N 0.000 description 1
- 229920002160 Celluloid Polymers 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 1
- CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 1
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- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011324 bead Substances 0.000 description 1
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- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- 235000019437 butane-1,3-diol Nutrition 0.000 description 1
- 125000006226 butoxyethyl group Chemical group 0.000 description 1
- 239000003518 caustics Substances 0.000 description 1
- 229910000420 cerium oxide Inorganic materials 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- KBLWLMPSVYBVDK-UHFFFAOYSA-N cyclohexyl prop-2-enoate Chemical compound C=CC(=O)OC1CCCCC1 KBLWLMPSVYBVDK-UHFFFAOYSA-N 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
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- 239000002270 dispersing agent Substances 0.000 description 1
- 238000009713 electroplating Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- VGIYPVFBQRUBDD-UHFFFAOYSA-N ethenoxycyclohexane Chemical compound C=COC1CCCCC1 VGIYPVFBQRUBDD-UHFFFAOYSA-N 0.000 description 1
- ORBFAMHUKZLWSD-UHFFFAOYSA-N ethyl 2-(dimethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(C)C ORBFAMHUKZLWSD-UHFFFAOYSA-N 0.000 description 1
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- 238000011156 evaluation Methods 0.000 description 1
- 238000013007 heat curing Methods 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
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- 239000003999 initiator Substances 0.000 description 1
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- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000005641 methacryl group Chemical group 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 1
- LSWADWIFYOAQRZ-UHFFFAOYSA-N n-(ethoxymethyl)prop-2-enamide Chemical compound CCOCNC(=O)C=C LSWADWIFYOAQRZ-UHFFFAOYSA-N 0.000 description 1
- DNTMQTKDNSEIFO-UHFFFAOYSA-N n-(hydroxymethyl)-2-methylprop-2-enamide Chemical compound CC(=C)C(=O)NCO DNTMQTKDNSEIFO-UHFFFAOYSA-N 0.000 description 1
- UGVYTRVYOYKZSO-UHFFFAOYSA-N n-butoxy-2-methylprop-2-enamide Chemical compound CCCCONC(=O)C(C)=C UGVYTRVYOYKZSO-UHFFFAOYSA-N 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 125000003544 oxime group Chemical group 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- LXTZRIBXKVRLOA-UHFFFAOYSA-N padimate a Chemical compound CCCCCOC(=O)C1=CC=C(N(C)C)C=C1 LXTZRIBXKVRLOA-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- 238000005502 peroxidation 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
- 230000000704 physical effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000003505 polymerization initiator Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 150000004060 quinone imines Chemical class 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- 150000003384 small molecules Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 238000009966 trimming Methods 0.000 description 1
- KOZCZZVUFDCZGG-UHFFFAOYSA-N vinyl benzoate Chemical compound C=COC(=O)C1=CC=CC=C1 KOZCZZVUFDCZGG-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
- H05K3/285—Permanent coating compositions
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F226/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen
- C08F226/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen by a single or double bond to nitrogen
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F236/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds
- C08F236/02—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds
- C08F236/20—Copolymers of compounds having one or more unsaturated aliphatic radicals, at least one having two or more carbon-to-carbon double bonds the radical having only two carbon-to-carbon double bonds unconjugated
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/02—Printing inks
- C09D11/10—Printing inks based on artificial resins
- C09D11/101—Inks specially adapted for printing processes involving curing by wave energy or particle radiation, e.g. with UV-curing following the printing
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- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D11/00—Inks
- C09D11/30—Inkjet printing inks
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- H—ELECTRICITY
- H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K2203/00—Indexing scheme relating to apparatus or processes for manufacturing printed circuits covered by H05K3/00
- H05K2203/01—Tools for processing; Objects used during processing
- H05K2203/0104—Tools for processing; Objects used during processing for patterning or coating
- H05K2203/013—Inkjet printing, e.g. for printing insulating material or resist
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- H05K—PRINTED CIRCUITS; CASINGS OR CONSTRUCTIONAL DETAILS OF ELECTRIC APPARATUS; MANUFACTURE OF ASSEMBLAGES OF ELECTRICAL COMPONENTS
- H05K3/00—Apparatus or processes for manufacturing printed circuits
- H05K3/22—Secondary treatment of printed circuits
- H05K3/28—Applying non-metallic protective coatings
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- Non-Metallic Protective Coatings For Printed Circuits (AREA)
Description
本發明係有關適合於製造印刷電路板之耐熱性優異的噴墨用硬化性樹脂組成物,及其硬化物以及使用其之印刷電路板者。更詳細而言,係有關製造印刷電路板中使用之阻焊劑或標記油墨中使用之在低黏度的操作性、儲存穩定性優越,且耐熱性、耐藥品性、無電解鍍金之耐性優異的噴墨用硬化性樹脂組成物,及其硬化物以及使用其之印刷電路板者。
目前,一部份之民生用品印刷電路板及幾乎全部之工業用印刷電路板所使用的光阻油墨組成物,從高精確度、高密度之觀點而言,在照射紫外線後,藉由進行顯像形成畫像,使用以熱及光照射進行修整硬化(本硬化)之液狀顯像型阻焊劑。又,顧慮對環境問題之影響,使用稀鹼水溶液作為顯像液之鹼顯像型的液狀阻焊劑成為主流。使用如此之稀鹼水溶液的鹼顯像型之光阻油墨組成物有,例如由在酚醛型環氧樹脂與含不飽和基之單羧酸的反應生成物中附加酸酐之含羧基感光性樹脂、光聚合引發劑、稀釋劑及環氧樹脂所成之光阻油墨組成物的揭示(參照專利文獻1)。
不過,此等阻焊劑組成物,由於含羧基感光性樹脂與環氧樹脂的反應性高之故,為二液型;因此,於使用前進
行混合,有必須在數日內使用之問題。
又,此等阻焊劑組成物,必要塗佈、乾燥、曝光、顯像、熱硬化等多數之步驟;又,此等步驟中必要塗佈機、乾燥機、曝光機、顯像機、熱硬化爐等設備,有製造成本增加之缺點。
因此之故,有以噴墨印刷機描繪,進行乾燥,製成阻焊劑圖型之提案(參照專利文獻2)。但是,與網版印刷法之油墨黏度為2,000~15,000mPa.s(25℃)比較,噴墨的油墨黏度低至10~150mPa.s(25℃)之故,在如此之方法中,藉由乾燥中之熱使油墨黏度更為降低,產生滲色不能獲得充分的精確度,難以達成實用化。
又,為進行低黏度化,使用低分子量之化合物例如三羥甲基丙烷三環氧丙基醚等環氧樹脂、或三烯丙基三聚異氰酸酯(TAIC)等作為稀釋劑之組成物,有耐熱性或硬化性欠佳的問題。另一方面,使用較低分子量且具有耐熱性之雙烯丙基納迪醯亞胺化合物的組成物,一般而言,有必要於250℃前後之高溫進行硬化的問題之故,有採用過氧化物予以硬化之方法的提案(參照專利文獻3)。不過,使用採用過氧化物之組成物於印刷電路板時,銅箔等金屬表面之氧化加激,有造成物性降低的問題。
專利文獻1:特開昭61-243869號公報(申請專利範圍)
專利文獻2:特開平7-263845號公報(申請專利範圍)
專利文獻3:特開平7-18031號公報(申請專利範圍)
本發明鑑於上述各種問題,其主要目的為提供適合於製造印刷電路板之低黏度、操作性及儲存穩定性優越,且具有優異之耐熱性、耐藥品性、無電解鍍金之耐性的噴墨用硬化性樹脂組成物,及其硬化物以及使用其印刷電路板。
為達成該目的,本發明之基本形態係提供一種噴墨用硬化性樹脂組成物,其特徵為含有:(A)下述一般式(1)所示之雙烯丙基納迪醯亞胺化合物、與(B)下述一般式(2)所示之雙馬來醯亞胺化合物、及(C)稀釋劑。
於25℃之黏度為150mPa.s以下。
式中,R1
為碳數2~18之烷基、芳基、或芳烷基。
式中,R2
為碳數2~32之烷基、芳基、或芳烷基。
又,較佳之形態係提供,該稀釋劑(C)為有機溶劑(C-1)、或聚合性單體(C-2)之噴墨用硬化性樹脂組成物。於此,聚合性單體(C-2)以具有丙烯醯基及/或甲基丙烯醯基更佳。
進而,依本發明的其他之面,可提供以噴墨印刷機使該噴墨用硬化性樹脂組成物描繪所期望之圖型,經熱硬化而得硬化物,以及具有由其硬化物所成之阻焊劑的印刷電路板。
本發明之噴墨用硬化性樹脂組成物,藉由具有低黏度,能以噴墨印刷機進行塗佈;進而,使本發明之噴墨用硬化性樹脂組成物進行熱硬化所得的硬化物,具有優越的耐熱性之故,可使用為印刷電路板用之阻焊劑或標記油墨。藉由使用噴墨印刷機形成阻焊劑,可提升生產性,亦能對印刷電路板之低成本化有所貢獻。
進而,使用本發明之噴墨用硬化性樹脂組成物,藉由
採用噴墨印刷機形成阻焊劑,可簡化步驟、提升生產性,又可減少設備之維持費等,能實現低成本化。
本發明之工作同仁為解決上述之課題,經深入探討與不斷研究之結果發現,含有:(A)下述一般式(1)所示之雙烯丙基納迪醯亞胺化合物、與(B)下述一般式(2)所示之雙馬來醯亞胺化合物、及(C)稀釋劑之組成物,在使用於印刷電路板之阻焊劑或標記油墨維持必要之特性的狀態,可達到能以噴墨印刷機塗佈之於25℃為150mPa.s以下的黏度,完成本發明。
式中,R1
為碳數2~18之烷基、芳基、或芳烷基。
式中,R2
為碳數2~32之烷基、芳基、或芳烷基。
即,本發明之一般式(1)所示的雙烯丙基納迪醯亞胺化合物(A),單獨不在250℃前後加熱時不能進行熱硬化,藉由併用本發明之特徵的一般式(2)所示之雙馬來醯亞胺化合物(B),可使硬化溫度降至一般製造印刷電路板所使用之100~200℃,較佳為140~180℃。又,藉由併用該雙烯丙基納迪醯亞胺化合物(A)與該雙馬來醯亞胺化合物(B),使雙馬來醯亞胺化合物(B)之結晶性降低,進而藉由添加稀釋劑(C),能提供低黏度且儲存穩定性優越之液狀組成物。
就本發明之噴墨用硬化性樹脂組成物的各構成成份詳細說明如下。
首先,本發明中所使用之雙烯丙基納迪醯亞胺化合物(A),有下述一般式(1)所示之化合物,較佳者有R1
為下述式(3)、(4)及(5)所示之化合物;具體而言,有丸善石油化學公司製之BANI-M、BANI-H、BANI-X(均為製品等級名)等。
式中,R1
為碳數2~18之烷基、芳基、或芳烷基。
此等雙烯丙基納迪醯亞胺化合物(A),可單獨或兩種以上混合使用;其配合量,在扣除後之稀釋劑(C)中使用的有機溶劑之組成物中,以30~96質量%之範圍為佳。
還有,因應需求亦可配合具有稀釋效果之單烯丙基萘酚二醯亞胺,例如丸善石油化學公司製之ANI-HP(製品等級名)。
本發明所使用之該雙馬來醯亞胺化合物(B),有下述一般式(2)所示之化合物,較佳者有R2
為下述式(6)、(7)、(8)及(9)所示之化合物;具體而言,有K.I化成公司製之BMI、BMI-70、BMI-80(均為製品等級名),大和化成工業公司製之BMI-1000、BMI-3000、BMI-4000、BMI-5000(均為製品等級名)等。
式中,R2
為碳數2~32之烷基、芳基、或芳烷基。
此等雙馬來醯亞胺化合物(B),可單獨或兩種以上混合使用;其配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份為4~45質量份,較佳為15~35質量份。雙馬來醯亞胺化合物(B)之配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份,未達4質量份時,硬化性降低,甚不適合;另一方面,相對於該雙烯丙基納迪
醯亞胺化合物(A)100質量份,超過45質量份時,耐熱性或硬化性降低,結晶性增強,成為噴墨噴嘴堵塞之原因,極不適合。
還有,因應需求亦可配合具有稀釋效果之單馬來酸酐縮亞胺,例如苯基馬來酸酐縮亞胺或環己基馬來酸酐縮亞胺;具有提升硬化性效果之由苯胺樹脂衍生的多官能馬來酸酐縮亞胺化合物,例如BMI-2000(製品等級名)等。
本發明中所使用之稀釋劑(C),使用有機溶劑(C-1)、及/或聚合性單體(C-2)、聚合性單體(C-2)以具有丙烯醯基及/或甲基丙烯醯基者為佳。
該有機溶劑(C-1)可使用甲乙酮、環己酮等酮類;甲苯、二甲苯、四甲基苯等芳香族烴類;溶纖劑、甲基溶纖劑、丁基溶纖劑、卡必醇、甲基卡必醇、丁基卡必醇、丙二醇單甲醚、二丙二醇單甲醚、二丙二醇二乙醚、三丙二醇單甲醚等二醇醚類;乙酸乙酯、乙酸丁酯、乳酸丁酯、溶纖劑乙酸酯、丁基溶纖劑乙酸酯、卡必醇乙酸酯、丁基卡必醇乙酸酯、丙二醇單甲醚乙酸酯、二丙二醇單甲醚乙酸酯、碳酸丙烯基酯等酯類;辛烷、癸烷等脂肪族烴類;石油醚、石腦油、溶劑石腦油等石油系溶劑等眾所周知的慣用有機溶劑。此等有機溶劑可單獨或兩種以上組合使用。
該聚合性單體(C-2),有苯乙烯、氯苯乙烯、α-甲基苯乙烯等苯乙烯衍生物;乙酸乙烯基酯、丁酸乙烯基酯或苯甲酸乙烯基酯等乙烯基酯類;乙烯基異丁基醚、乙烯
基正丁基醚、乙烯基叔丁基醚、乙烯基正戊基醚、乙烯基異戊基醚、乙胺基正(十八)烷基醚、乙烯基環己基醚、乙二醇單丁基乙烯基醚、三乙二醇單甲基乙烯基醚等乙烯基醚類;丙烯醯胺、甲基丙烯醯胺、N-羥基甲基丙烯醯胺、N-羥甲基甲基丙烯醯胺、N-甲氧基甲基丙烯醯胺、N-乙氧基甲基丙烯醯胺、N-丁氧基甲基丙烯醯胺等(甲基)丙烯醯胺類;三烯丙基三聚異氰酸酯、苯二甲酸二烯丙基酯、異苯二甲酸二烯丙基酯等烯丙基化合物;(甲基)丙烯酸2-乙基己基酯、(甲基)丙烯酸(十二)烷基酯、(甲基)丙烯酸異(十八)烷基酯、(甲基)丙烯酸2-羥基乙基酯、(甲基)丙烯酸2-羥基丙基酯、(甲基)丙烯酸2-甲氧基乙基酯、(甲基)丙烯酸異丁基酯、(甲基)丙烯酸叔丁基酯、(甲基)丙烯酸丁氧基乙基酯、(甲基)丙烯酸甲基三甘醇酯、丙烯酸環己基酯、丙烯酸2-乙基己基卡必醇酯、(甲基)丙烯酸4-羥基丁基酯、(甲基)丙烯酸異冰片烷基酯、(甲基)丙烯酸甲氧基二乙二醇酯、(甲基)丙烯酸乙氧基二乙二醇酯、(甲基)丙烯酸3-甲氧基丁基酯、(甲基)丙烯酸甲氧基丙二醇酯、(甲基)丙烯酸苄基酯、(甲基)丙烯酸苯氧基乙基酯、1,3-丁二醇二(甲基)丙烯酸酯、1,5-戊二醇二(甲基)丙烯酸酯、季戊二醇二(甲基)丙烯酸酯、(甲基)丙烯酸四氫糠基酯、1,6-己二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、4-(甲基)丙烯醯基氧甲基-2-甲基-2-乙基-1,3-二氧五圜、4-(甲基
)丙烯醯基氧甲基-2-異丁基-2-乙基-1,3-二氧五圜、4-(甲基)丙烯醯基氧甲基-2-環己基-1,3-二氧五圜、三羥甲基丙烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇六(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯等1分子中具有一個以上之丙烯醯基及/或甲基丙烯醯基之化合物等。
此等之中,以1分子中具有1~4個之丙烯醯基及/或甲基丙烯醯基之化合物為佳。進而以黏度可達25℃下為300mPa.s以下之化合物更佳。
此等聚合性單體(C-2),可單獨或兩種以上混合使用。
還有,本說明書中,所謂(甲基)丙烯酸酯,係丙烯酸酯、甲基丙烯酸酯、及此等之混合物的總稱之用語,其他類似者亦同。
此等稀釋劑(C)之配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份,為25~1900質量份,較佳為40~400質量份。但,稀釋劑(C)為聚合性單體(C-2)單獨時,為25~200質量份。稀釋劑(C)之配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份,未達25質量份時,造成該雙烯丙基納迪醯亞胺化合物(A)之溶解不良,導致高黏度化而不能塗佈,甚不適合。另一方面,稀釋劑(C)為有機溶劑(C-1)時,其配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份,超過1900
質量份時,固形份之含量減少,難以確保膜厚。又,稀釋劑(C)為聚合性單體(C-2)單獨時,其配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份,超過200質量份時,容易造成硬化時之塗膜破裂,極不適合。
本發明之噴墨用硬化性樹脂組成物中,為提升硬化性可配合藉由熱或照射活性能量線產生游離基之游離基聚合引發劑(D)。如此之游離基聚合引發劑(D),除使銅箔等金屬表面氧化之過氧化物以外,可使用眾所周知的慣用之聚合引發劑,例如苯偶姻、苯偶姻甲基醚、苯偶姻乙基醚、苯偶姻丙基醚等苯偶姻與苯偶姻烷基醚類;苯乙酮、2,2-二甲氧基-2-苯基苯乙酮、2,2-二乙氧基-2-苯基苯乙酮、1,1-二氯苯乙酮等苯乙酮類;2-甲基-1-[4-(甲硫基)苯基]-2-嗎啉代-丙烷-1-酮、2-苄基-2-二甲基胺基-1-(4-嗎啉代苯基)-丁烷-1-酮、N,N-二甲基胺基苯乙酮等胺基苯乙酮類;2-甲基蒽醌、2-乙基蒽醌、2-叔丁基蒽醌、1-氯蒽醌等蒽醌類;2,4-二甲基噻噸酮、2,4-二乙基噻噸酮、2-氯噻噸酮、2,4-二異丙基噻噸酮等噻噸酮類;苯乙酮二甲基縮酮、苄基二甲基縮酮等縮酮類;二苯甲酮、4,4’-雙二甲基胺基二苯甲酮等二苯甲酮類或呫噸酮類;2,4,6-三甲基苯甲醯基二苯基膦氧化物、或2-三氯甲基-5-苯乙烯基-1,3,4-噁二唑、2-三氯甲基-5-(對-氰基苯乙烯基)-1,3,4-噁二唑等鹵甲基噁二唑系化合物;2,4-雙(三氯甲基)-6-(對-甲氧基-苯基乙烯基-1,3,5-三嗪、2,4-雙(三氯甲基)-6-對-甲氧基苯乙烯基-s-三嗪、2,4-雙(三氯甲基
)-6-(1-對-二甲基胺基苯基-1,3-丁二烯基)-s-三嗪等鹵甲基-s-三嗪系化合物等。
進而,可加入N,N-二甲基胺基苯甲酸乙基酯、N,N-二甲基胺基苯甲酸異戊基酯、戊基-4-二甲基胺基苯甲酸酯、三乙胺、三乙醇胺等叔胺類等聚合引發助劑。
此等游離基聚合引發劑(D),可單獨或兩種以上混合使用;其配合量,在扣除該稀釋劑(C)之有機溶劑(C-1)的組成物中,為10質量%以下,較佳為0.5~5質量%。游離基聚合引發劑(D)之配合量超過10質量%時,造成塗膜特性降低,甚不適合。
進而,本發明之噴墨用硬化性樹脂組成物中,因應需求可配合毫微二氧化矽等超微粉之無機填充劑、氧化鈦等無機顏料。
此等之配合量,相對於光阻組成物之不揮發份100質量份,以30質量份以下為佳。配合量超過30質量份時,光阻組成物之黏度上升,使噴墨塗佈性下降,硬化性降低之故甚不適合。
又,可配合雙氰胺、鄰-甲苯基雙胍、鳥糞胺、甲基胍胺、苯并鳥糞胺等鳥糞胺類、三聚氰胺等抗氧化劑;蒽醌系、苝系、二偶氮系、異吲哚滿系、酞菁系等有機顏料;消泡劑;黏著性賦予劑;平坦化劑;顏料分散劑等各種添加劑類。
此等添加劑之配合量,相對於光阻組成物之不揮發份100質量份,為5質量份以下。添加劑之配合量超過5質量%
時,光阻組成物之黏度上升,使噴墨塗佈性下降,塗膜特性降低之故極不適合。
配合上述成份所得之本發明的噴墨用硬化性樹脂組成物,使用攪拌機或分散機,例如滾筒研磨機、砂磨機、球磨機、珠磨機或阿多萊達等分散機進行混合.分散,調整至均勻為止。
如此而得之本發明的噴墨用硬化性樹脂組成物,以稀釋劑(C)調整黏度至可使用噴墨印刷機塗佈之於25℃為150mPa.s以下,較佳為110~5mPa.s。
經如此調整之本發明的噴墨用硬化性樹脂組成物,使用噴墨印刷機在形成電路之印刷電路板表面描繪所期望之圖型,其後藉由於100~200℃,較佳為140~180℃進行10~60分鐘之熱硬化,可獲得由耐熱性等優越之硬化物所成的光阻圖型。又,使用聚合性單體(C-2)作為該稀釋劑,配合藉由照射活性能量線產生游離基之該游離基聚合引發劑(D)的組成物之情況,在使用噴墨印刷機於形成電路之印刷電路板表面描繪所期望的圖型後,藉由照射紫外線等活性能量線進行光硬化,可形成極少滲色之圖型,其後進而藉由於100~200℃,較佳為140~180℃,加熱10~60分鐘進行熱硬化,能獲得由耐熱性等優越之硬化物所成的光阻圖型。
上述噴墨印刷機,適合使用啟通需求.壓電方式之噴墨印刷機,可使噴嘴於室溫,或加溫至60℃以下進行塗佈。
又,該活性能量線之照射光源,以低壓水銀燈、中壓水銀燈、高壓水銀燈、超高壓水銀燈、氙氣燈或金屬鹵化物燈較為適合;亦可使用雷射光線等作為活性能量線。
不必要如鹼顯像型阻焊劑之複雜的步驟之故,能提供低優格、且全無離子性物質等黏附、高信賴性之印刷電路板。
以實施例等具體說明本發明如下;本發明並非限定於此等實施例者。還有,下述中除特別規定以外,「份」為重量份之意。
使下述之表1所示的配合成份進行混合.攪拌,以1 μm之過濾網進行過濾,即得噴墨用硬化性樹脂組成物。
在測定如上所述而得之噴墨用硬化性樹脂組成物的黏度後,使用啟通需求.壓電方式之噴墨印刷機,在形成電路之印刷電路板(FR-4)上塗佈阻焊劑圖型。實施例1係在塗佈後,以熱風循環式乾燥爐於160℃、30分鐘進行熱硬化。實施例2~11係在塗佈後,以UV輸送帶爐進行2,000mJ/cm2
曝光後,以熱風循環式乾燥爐於160℃、30分鐘進行熱硬化。
評估所得組成物之黏度及硬化塗膜之特性的結果,如表2所示。
上述表2中之性能試驗的評估方法,如下述之說明。
上述所得噴墨用硬化性樹脂組成物之於25℃的黏度,係由比重及動態黏度依下述方法求出。
還有,比重係使用比重計測定,動態黏度係使用佳能發斯克型黏度計測定。
黏度(mPa.s)=動態黏度(mm2
/s)×比重
依JIS K-5600-5-4之試驗方法,評估銅箔上之硬化塗膜的鉛筆硬度。
○:6H以上者
×:5H以下者
將硬化塗膜浸漬於丙二醇單甲醚乙酸酯中30分鐘後,評估塗膜狀態。
○:確認完全無改變者
△:稍微改變者
×:塗膜膨脹、剝離者
將硬化塗膜浸漬於10vol%之鹽酸10分鐘後,評估塗膜狀態。
○:確認完全無改變者
△:稍微改變者
×:塗膜膨脹、剝離者
將硬化塗膜浸漬於260℃之焊料槽中5秒鐘後,以賽璐發膠帶進行剝離試驗,評估塗膜狀態。
○:塗膜無改變者
△:塗膜變色者
×:塗膜剝離者
使用市售之無電解鍍鎳浴及無電解鍍金浴,以鎳為0.5 μm、金0.03 μm之條件進行電鍍,藉由膠帶剝離,評估硬化塗膜是否剝離,或有無電鍍滲入。
○:完全無剝落者
△:稍微剝落者
×:硬化塗膜剝落者
將硬化塗膜浸漬於丙酮後,以碎布擦拭,評估表面狀態。
○:完全無改變
×:表面溶解或軟化,附有傷痕。
使上述所得之噴墨用硬化性樹脂組成物在常溫下儲存一個月後,測定黏度;由其結果以下述之基準評估儲存穩定性。
○:常溫1個月後之增黏率為1.5倍以下者
×:常溫1個月後之增黏率超過1.5倍者
由表2之結果可知,實施例1~11之組成物,以在可實施印刷電路板之製造的條件(例如160℃、30分鐘),能硬化;進而,於低黏度的儲存穩定性優越之故,判定可使用為噴墨用硬化性樹脂組成物。另一方面,未配合雙馬來醯亞胺化合物之比較例1,在160℃、30分鐘之硬化中,不能充分硬化之故,塗膜硬度、耐溶劑性、焊料耐性等均不良。
Claims (10)
- 一種噴墨用硬化性樹脂組成物,其特徵為含有:(A)下述一般式(1)所示之雙烯丙基納迪醯亞胺化合物(bisallylnadiimide)與、(B)下述一般式(2)所示之雙馬來醯亞胺化合物、及(C)稀釋劑所成,於25℃之黏度為150mPa.s以下,
式中,R1 為碳數2~18之烷基、芳基、或芳烷基 式中,R2 為碳數2~32之烷基、芳基、或芳烷基。 - 如申請專利範圍第1項之噴墨用硬化性樹脂組成物,其中該稀釋劑(C)為有機溶劑(C-1)及/或聚合性單體(C-2)。
- 如申請專利範圍第2項之噴墨用硬化性樹脂組成物,其中該聚合性單體(C-2)為具有丙烯醯基及/或甲基丙烯醯基之聚合性單體。
- 如申請專利範圍第1項之噴墨用硬化性樹脂組成物,其中該雙烯丙基納迪醯亞胺化合物(A)之配合量為,扣除有機溶劑之組成物中之30~96質量%。
- 如申請專利範圍第1項之噴墨用硬化性樹脂組成物,其中該雙馬來醯亞胺化合物(B)之配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份為4~45質量份。
- 如申請專利範圍第2項或第3項之噴墨用硬化性樹脂組成物,其中該稀釋劑(C)之配合量,相對於該雙烯丙基納迪醯亞胺化合物(A)100質量份為25~1900質量份[但,稀釋劑(C)在聚合性單體(C-2)單獨之情況,為25~200質量份]。
- 一種硬化物,其特徵為使如申請專利範圍第1~6項中任一項之噴墨用硬化性樹脂組成物,以噴墨印刷機塗佈,進行熱硬化而得。
- 一種硬化物,其特徵為使如申請專利範圍第3項之噴墨用硬化性樹脂組成物,以噴墨印刷機塗佈,照射紫外線進行光硬化後,進而施行熱硬化而得。
- 一種具有阻焊劑之印刷電路板,其特徵為使如申請專利範圍第1~6項中任一項之噴墨用硬化性樹脂組成物,以噴墨印刷機塗佈於阻焊劑圖型上,進行熱硬化而得。
- 一種具有阻焊劑之印刷電路板,其特徵為使如申請專利範圍第3項之噴墨用硬化性樹脂組成物,以噴墨印刷機塗佈於阻焊劑圖型上,照射紫外線進行光硬化後,進而施行熱硬化而得。
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP2005004766 | 2005-01-12 |
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| TW200635983A TW200635983A (en) | 2006-10-16 |
| TWI391424B true TWI391424B (zh) | 2013-04-01 |
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| Application Number | Title | Priority Date | Filing Date |
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| TW95101064A TWI391424B (zh) | 2005-01-12 | 2006-01-11 | A hardened resin composition for inkjet and a hardened product thereof, and a printed circuit board using the same |
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| Country | Link |
|---|---|
| US (2) | US20070270568A1 (zh) |
| EP (1) | EP1857478B1 (zh) |
| JP (1) | JP5222475B2 (zh) |
| KR (1) | KR100890086B1 (zh) |
| CN (1) | CN101103057B (zh) |
| AT (1) | ATE441678T1 (zh) |
| DE (1) | DE602006008901D1 (zh) |
| TW (1) | TWI391424B (zh) |
| WO (1) | WO2006075654A1 (zh) |
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- 2006-01-12 AT AT06711602T patent/ATE441678T1/de active
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Also Published As
| Publication number | Publication date |
|---|---|
| KR100890086B1 (ko) | 2009-03-24 |
| CN101103057B (zh) | 2010-10-13 |
| KR20070089226A (ko) | 2007-08-30 |
| CN101103057A (zh) | 2008-01-09 |
| DE602006008901D1 (de) | 2009-10-15 |
| WO2006075654A1 (ja) | 2006-07-20 |
| JPWO2006075654A1 (ja) | 2008-06-12 |
| US20070270568A1 (en) | 2007-11-22 |
| EP1857478A4 (en) | 2008-05-14 |
| US20110120753A1 (en) | 2011-05-26 |
| EP1857478A1 (en) | 2007-11-21 |
| TW200635983A (en) | 2006-10-16 |
| JP5222475B2 (ja) | 2013-06-26 |
| EP1857478B1 (en) | 2009-09-02 |
| ATE441678T1 (de) | 2009-09-15 |
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