CN106832221A - The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it - Google Patents
The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it Download PDFInfo
- Publication number
- CN106832221A CN106832221A CN201710087190.9A CN201710087190A CN106832221A CN 106832221 A CN106832221 A CN 106832221A CN 201710087190 A CN201710087190 A CN 201710087190A CN 106832221 A CN106832221 A CN 106832221A
- Authority
- CN
- China
- Prior art keywords
- photocuring
- heat reactive
- resin
- reactive resin
- structure containing
- 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
- 229920005989 resin Polymers 0.000 title claims abstract description 58
- 239000011347 resin Substances 0.000 title claims abstract description 58
- 238000000016 photochemical curing Methods 0.000 title claims abstract description 53
- 239000000463 material Substances 0.000 title claims abstract description 44
- 229910000679 solder Inorganic materials 0.000 title claims abstract description 40
- IZXIZTKNFFYFOF-UHFFFAOYSA-N 2-Oxazolidone Chemical compound O=C1NCCO1 IZXIZTKNFFYFOF-UHFFFAOYSA-N 0.000 title claims abstract description 28
- 238000002360 preparation method Methods 0.000 title claims abstract description 23
- 238000006243 chemical reaction Methods 0.000 claims abstract description 34
- 239000003822 epoxy resin Substances 0.000 claims abstract description 29
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 29
- 239000002904 solvent Substances 0.000 claims abstract description 25
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 23
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims abstract description 13
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims abstract description 12
- 239000003054 catalyst Substances 0.000 claims abstract description 12
- 238000012544 monitoring process Methods 0.000 claims abstract description 10
- -1 magnesium-triphenylphosphine oxide Chemical compound 0.000 claims description 42
- 239000002253 acid Substances 0.000 claims description 25
- 150000002148 esters Chemical class 0.000 claims description 21
- 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 claims description 14
- 239000002585 base Substances 0.000 claims description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 9
- 229910052796 boron Inorganic materials 0.000 claims description 9
- 239000003513 alkali Substances 0.000 claims description 8
- 239000004593 Epoxy Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 7
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 claims description 6
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 claims description 6
- 239000004843 novolac epoxy resin Substances 0.000 claims description 6
- 229920001187 thermosetting polymer Polymers 0.000 claims description 6
- VNDYJBBGRKZCSX-UHFFFAOYSA-L zinc bromide Chemical compound Br[Zn]Br VNDYJBBGRKZCSX-UHFFFAOYSA-L 0.000 claims description 6
- KXGFMDJXCMQABM-UHFFFAOYSA-N 2-methoxy-6-methylphenol Chemical compound [CH]OC1=CC=CC([CH])=C1O KXGFMDJXCMQABM-UHFFFAOYSA-N 0.000 claims description 5
- 229920000178 Acrylic resin Polymers 0.000 claims description 5
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 claims description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 5
- 229920001568 phenolic resin Polymers 0.000 claims description 5
- 239000005011 phenolic resin Substances 0.000 claims description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 4
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 4
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 4
- 229930185605 Bisphenol Natural products 0.000 claims description 4
- 229920000877 Melamine resin Polymers 0.000 claims description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- 239000004411 aluminium Substances 0.000 claims description 4
- 229910052782 aluminium Inorganic materials 0.000 claims description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 claims description 4
- 235000010354 butylated hydroxytoluene Nutrition 0.000 claims description 4
- 239000004202 carbamide Substances 0.000 claims description 4
- 150000002513 isocyanates Chemical class 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 4
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical class O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 claims description 4
- 150000003866 tertiary ammonium salts Chemical class 0.000 claims description 4
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 3
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 3
- 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 claims description 3
- 239000004925 Acrylic resin Substances 0.000 claims description 3
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
- 229920000147 Styrene maleic anhydride Polymers 0.000 claims description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 claims description 3
- APZPSKFMSWZPKL-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(CO)CO APZPSKFMSWZPKL-UHFFFAOYSA-N 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- PYKYMHQGRFAEBM-UHFFFAOYSA-N anthraquinone Natural products CCC(=O)c1c(O)c2C(=O)C3C(C=CC=C3O)C(=O)c2cc1CC(=O)OC PYKYMHQGRFAEBM-UHFFFAOYSA-N 0.000 claims description 3
- 150000004056 anthraquinones Chemical class 0.000 claims description 3
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 claims description 3
- SRKKQWSERFMTOX-UHFFFAOYSA-N cyclopentane;titanium Chemical compound [Ti].[CH]1C=CC=C1 SRKKQWSERFMTOX-UHFFFAOYSA-N 0.000 claims description 3
- VOOLKNUJNPZAHE-UHFFFAOYSA-N formaldehyde;2-methylphenol Chemical compound O=C.CC1=CC=CC=C1O VOOLKNUJNPZAHE-UHFFFAOYSA-N 0.000 claims description 3
- VVTZNCQOVBDXRL-UHFFFAOYSA-N guanidine;propanoic acid Chemical compound NC(N)=N.CCC(O)=O VVTZNCQOVBDXRL-UHFFFAOYSA-N 0.000 claims description 3
- 150000002632 lipids Chemical class 0.000 claims description 3
- 229910052749 magnesium Inorganic materials 0.000 claims description 3
- 239000011777 magnesium Substances 0.000 claims description 3
- 229920003986 novolac Polymers 0.000 claims description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 3
- 150000003512 tertiary amines Chemical class 0.000 claims description 3
- 229940102001 zinc bromide Drugs 0.000 claims description 3
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 claims description 2
- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 claims description 2
- QNHABHBGHRFSPJ-UHFFFAOYSA-K C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-] Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.[Cl-].[Al+3].[Cl-].[Cl-] QNHABHBGHRFSPJ-UHFFFAOYSA-K 0.000 claims description 2
- YFPJFKYCVYXDJK-UHFFFAOYSA-N Diphenylphosphine oxide Chemical compound C=1C=CC=CC=1[P+](=O)C1=CC=CC=C1 YFPJFKYCVYXDJK-UHFFFAOYSA-N 0.000 claims description 2
- 239000005058 Isophorone diisocyanate Substances 0.000 claims description 2
- 150000007942 carboxylates Chemical class 0.000 claims description 2
- 229940091853 isobornyl acrylate Drugs 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 2
- 229920005749 polyurethane resin Polymers 0.000 claims description 2
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 claims description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 claims 2
- HBGPNLPABVUVKZ-POTXQNELSA-N (1r,3as,4s,5ar,5br,7r,7ar,11ar,11br,13as,13br)-4,7-dihydroxy-3a,5a,5b,8,8,11a-hexamethyl-1-prop-1-en-2-yl-2,3,4,5,6,7,7a,10,11,11b,12,13,13a,13b-tetradecahydro-1h-cyclopenta[a]chrysen-9-one Chemical compound C([C@@]12C)CC(=O)C(C)(C)[C@@H]1[C@H](O)C[C@]([C@]1(C)C[C@@H]3O)(C)[C@@H]2CC[C@H]1[C@@H]1[C@]3(C)CC[C@H]1C(=C)C HBGPNLPABVUVKZ-POTXQNELSA-N 0.000 claims 1
- PFRGGOIBYLYVKM-UHFFFAOYSA-N 15alpha-hydroxylup-20(29)-en-3-one Natural products CC(=C)C1CCC2(C)CC(O)C3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 PFRGGOIBYLYVKM-UHFFFAOYSA-N 0.000 claims 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 claims 1
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 claims 1
- SOKRNBGSNZXYIO-UHFFFAOYSA-N Resinone Natural products CC(=C)C1CCC2(C)C(O)CC3(C)C(CCC4C5(C)CCC(=O)C(C)(C)C5CCC34C)C12 SOKRNBGSNZXYIO-UHFFFAOYSA-N 0.000 claims 1
- SNMUMYFMLRZUFC-UHFFFAOYSA-N [AlH3].O1CCCC1 Chemical compound [AlH3].O1CCCC1 SNMUMYFMLRZUFC-UHFFFAOYSA-N 0.000 claims 1
- 239000010426 asphalt Substances 0.000 claims 1
- 238000005660 chlorination reaction Methods 0.000 claims 1
- 239000000460 chlorine Substances 0.000 claims 1
- 229910052801 chlorine Inorganic materials 0.000 claims 1
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical group C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 claims 1
- WDGCBNTXZHJTHJ-UHFFFAOYSA-N 2h-1,3-oxazol-2-id-4-one Chemical group O=C1CO[C-]=N1 WDGCBNTXZHJTHJ-UHFFFAOYSA-N 0.000 abstract description 19
- 239000000853 adhesive Substances 0.000 abstract description 12
- 230000001070 adhesive effect Effects 0.000 abstract description 12
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 abstract description 7
- 238000002329 infrared spectrum Methods 0.000 abstract description 7
- WYNCHZVNFNFDNH-UHFFFAOYSA-N Oxazolidine Chemical compound C1COCN1 WYNCHZVNFNFDNH-UHFFFAOYSA-N 0.000 abstract description 2
- 150000002576 ketones Chemical class 0.000 abstract description 2
- 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 abstract 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 30
- 239000000047 product Substances 0.000 description 17
- 238000000576 coating method Methods 0.000 description 13
- OWIKHYCFFJSOEH-UHFFFAOYSA-N Isocyanic acid Chemical compound N=C=O OWIKHYCFFJSOEH-UHFFFAOYSA-N 0.000 description 12
- XLJMAIOERFSOGZ-UHFFFAOYSA-N anhydrous cyanic acid Natural products OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 12
- 239000003921 oil Substances 0.000 description 9
- 239000011248 coating agent Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000013007 heat curing Methods 0.000 description 7
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 5
- 239000000945 filler Substances 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 4
- 150000001412 amines Chemical class 0.000 description 4
- 150000001875 compounds Chemical class 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical group NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 4
- 125000003700 epoxy group Chemical group 0.000 description 4
- 238000005187 foaming Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 229910002012 Aerosil® Inorganic materials 0.000 description 3
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 3
- 239000002390 adhesive tape Substances 0.000 description 3
- WXLFIFHRGFOVCD-UHFFFAOYSA-L azophloxine Chemical compound [Na+].[Na+].OC1=C2C(NC(=O)C)=CC(S([O-])(=O)=O)=CC2=CC(S([O-])(=O)=O)=C1N=NC1=CC=CC=C1 WXLFIFHRGFOVCD-UHFFFAOYSA-L 0.000 description 3
- 239000000440 bentonite Substances 0.000 description 3
- 229910000278 bentonite Inorganic materials 0.000 description 3
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 3
- 229910000019 calcium carbonate Inorganic materials 0.000 description 3
- 239000006229 carbon black Substances 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical group O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 3
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 235000012739 red 2G Nutrition 0.000 description 3
- 239000011863 silicon-based powder Substances 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- AUHZEENZYGFFBQ-UHFFFAOYSA-N 1,3,5-trimethylbenzene Chemical compound CC1=CC(C)=CC(C)=C1 AUHZEENZYGFFBQ-UHFFFAOYSA-N 0.000 description 2
- BTJPUDCSZVCXFQ-UHFFFAOYSA-N 2,4-diethylthioxanthen-9-one Chemical class C1=CC=C2C(=O)C3=CC(CC)=CC(CC)=C3SC2=C1 BTJPUDCSZVCXFQ-UHFFFAOYSA-N 0.000 description 2
- CUDYYMUUJHLCGZ-UHFFFAOYSA-N 2-(2-methoxypropoxy)propan-1-ol Chemical compound COC(C)COC(C)CO CUDYYMUUJHLCGZ-UHFFFAOYSA-N 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- VTPRYOMNAIGCLD-UHFFFAOYSA-L C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.[Cl-].[Mg+2].[Cl-] Chemical compound C1(=CC=CC=C1)P(C1=CC=CC=C1)(C1=CC=CC=C1)=O.[Cl-].[Mg+2].[Cl-] VTPRYOMNAIGCLD-UHFFFAOYSA-L 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- QBBWRNBMWSVXBB-UHFFFAOYSA-K aluminum;oxolane;trichloride Chemical compound Cl[Al](Cl)Cl.C1CCOC1 QBBWRNBMWSVXBB-UHFFFAOYSA-K 0.000 description 2
- 150000001450 anions Chemical class 0.000 description 2
- 239000004020 conductor Substances 0.000 description 2
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 229940028356 diethylene glycol monobutyl ether Drugs 0.000 description 2
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical group CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000005611 electricity Effects 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 230000004907 flux Effects 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JCGNDDUYTRNOFT-UHFFFAOYSA-N oxolane-2,4-dione Chemical compound O=C1COC(=O)C1 JCGNDDUYTRNOFT-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 2
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000007639 printing Methods 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
- 238000007650 screen-printing Methods 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 238000007711 solidification Methods 0.000 description 2
- 230000008023 solidification Effects 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 1
- YFVZPDCNRWNHNX-UHFFFAOYSA-N 1-(2-phenyl-1h-imidazol-5-yl)ethanamine Chemical class N1C(C(N)C)=CN=C1C1=CC=CC=C1 YFVZPDCNRWNHNX-UHFFFAOYSA-N 0.000 description 1
- WMDZKDKPYCNCDZ-UHFFFAOYSA-N 2-(2-butoxypropoxy)propan-1-ol Chemical compound CCCCOC(C)COC(C)CO WMDZKDKPYCNCDZ-UHFFFAOYSA-N 0.000 description 1
- BJINVQNEBGOMCR-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethyl acetate Chemical compound COCCOCCOC(C)=O BJINVQNEBGOMCR-UHFFFAOYSA-N 0.000 description 1
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 1
- NQBXSWAWVZHKBZ-UHFFFAOYSA-N 2-butoxyethyl acetate Chemical compound CCCCOCCOC(C)=O NQBXSWAWVZHKBZ-UHFFFAOYSA-N 0.000 description 1
- 150000004941 2-phenylimidazoles Chemical class 0.000 description 1
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical class N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 description 1
- CGLVZFOCZLHKOH-UHFFFAOYSA-N 8,18-dichloro-5,15-diethyl-5,15-dihydrodiindolo(3,2-b:3',2'-m)triphenodioxazine Chemical compound CCN1C2=CC=CC=C2C2=C1C=C1OC3=C(Cl)C4=NC(C=C5C6=CC=CC=C6N(C5=C5)CC)=C5OC4=C(Cl)C3=NC1=C2 CGLVZFOCZLHKOH-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
- WRFMXTSFJSLZSW-UHFFFAOYSA-N C(C)OC(C(C(O)OCC)(C)C)O Chemical compound C(C)OC(C(C(O)OCC)(C)C)O WRFMXTSFJSLZSW-UHFFFAOYSA-N 0.000 description 1
- WTNMMKJWWSEFNO-UHFFFAOYSA-N CC(C)[S] Chemical compound CC(C)[S] WTNMMKJWWSEFNO-UHFFFAOYSA-N 0.000 description 1
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 description 1
- XEUCQOBUZPQUMQ-UHFFFAOYSA-N Glycolone Chemical compound COC1=C(CC=C(C)C)C(=O)NC2=C1C=CC=C2OC XEUCQOBUZPQUMQ-UHFFFAOYSA-N 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- MPIAGWXWVAHQBB-UHFFFAOYSA-N [3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(COC(=O)C=C)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C MPIAGWXWVAHQBB-UHFFFAOYSA-N 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 229910021502 aluminium hydroxide Inorganic materials 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- RJGDLRCDCYRQOQ-UHFFFAOYSA-N anthrone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3CC2=C1 RJGDLRCDCYRQOQ-UHFFFAOYSA-N 0.000 description 1
- 150000003851 azoles Chemical class 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- QFFVPLLCYGOFPU-UHFFFAOYSA-N barium chromate Chemical compound [Ba+2].[O-][Cr]([O-])(=O)=O QFFVPLLCYGOFPU-UHFFFAOYSA-N 0.000 description 1
- 235000010290 biphenyl Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical compound C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000004568 cement Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- XXJWXESWEXIICW-UHFFFAOYSA-N diethylene glycol monoethyl ether Chemical compound CCOCCOCCO XXJWXESWEXIICW-UHFFFAOYSA-N 0.000 description 1
- 229940075557 diethylene glycol monoethyl ether Drugs 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N hydrazine Substances NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 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
- 238000004519 manufacturing process Methods 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 238000003801 milling Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- JLTDJTHDQAWBAV-UHFFFAOYSA-N phenyldimethylamine Natural products CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
- 238000001259 photo etching Methods 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001235 sensitizing effect Effects 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 235000011149 sulphuric acid Nutrition 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 0.000 description 1
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Substances C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/14—Polycondensates modified by chemical after-treatment
- C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
- C08G59/1477—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing nitrogen
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- General Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Materials For Photolithography (AREA)
Abstract
A kind of photosensitive solder resist material the present invention relates to the photocuring of structure containing oxazolidone heat reactive resin, its preparation method and containing it.Be added separately in solvent for diisocyanate, dibutyl tin laurate and pentaerythritol triacrylate in the preparation process of the photocuring heat reactive resin of structure containing oxazolidone by the invention, keep 70 DEG C of reaction temperature 40 DEG C, the change in concentration of NCO group in monitoring system, when NCO group content for initial content 48% 55% when stop reaction, obtain the addition product of diisocyanate half；Again by epoxy resin, catalyst and 2, the methylphenol of 6 di-t-butyl 4 is added separately in the addition product of the diisocyanate half, keep 140 DEG C of reaction temperature 110 DEG C, when NCO group in system content be 0 when stop reaction, after measured in infrared spectrum in Chu Xian oxazolidone ring structures carbonyl 1750cm‑1The absworption peak at place, that is, obtain the photocuring heat reactive resin of the ring of ketone containing oxazolidine.Photocuring heat reactive resin prepared by the invention has excellent heat resistance and preferable adhesive force.
Description
Technical field
The present invention relates to light-cured resin field, more particularly to a kind of photocuring heat cure tree of structure containing oxazolidone
Fat, its preparation method and the photosensitive solder resist material containing it.
Background technology
Printed circuit board (PCB) is the basic activity of hyundai electronicses industry, can be a large amount of in the manufacture of printed circuit board (PCB)
Use photosensitive solder resist material.In recent years due to the requirement and the national limitation to lead content in electronic product of environmental protection, printing electricity
The process of surface treatment of road plate (PCB) starts more to spray tin instead of traditional lead that has using lead-free tin spray, and lead-free tin spray is needed
Surface temperature that will be higher.But, traditional photosensitive solder resist material easily bubbles stripping in hot conditions, has a strong impact on circuit
Plate quality.
The content of the invention
Based on this, it is necessary to provide the photocuring heat cure of structure containing oxazolidone of a kind of high temperature resistant, stripping not easy to foaming
Resin, its preparation method and the photosensitive solder resist material containing it.
A kind of preparation method of the photocuring of structure containing oxazolidone heat reactive resin, comprises the following steps：
Diisocyanate, dibutyl tin laurate and pentaerythritol triacrylate are added separately in solvent, are protected
40 DEG C -70 DEG C of reaction temperature is held, in monitoring system-change in concentration of NCO group, when the content of-NCO group is initial content
Stop reaction during 48%-55%, obtain the addition product of diisocyanate half；
Epoxy resin, catalyst and 2,6 di tert butyl 4 methyl phenol are added separately to the diisocyanate half
In addition product, keep 110 DEG C -140 DEG C of reaction temperature, when in system-content of NCO group be 0 when stop reaction, that is, contained
Oxazolidone structure photocuring heat reactive resin.
Wherein in one embodiment, the pentaerythritol triacrylate is 1 with the mol ratio of the diisocyanate:
(1-1.05)；The diisocyanate is 100 with the mass ratio of the dibutyl tin laurate：(0.1-1)；Two isocyanide
Acid esters is 1 with the mass ratio of the dibasic acid ester:(0.11-0.2)；The epoxy resin epoxide epoxy group group and the intermediate flux
In-mol ratio of NCO group is 1:(0.5-0.8)；The epoxy resin is 100 with the mass ratio of the catalyst:(0.1-
1)；The epoxy resin is 100 with the 2,6 di tert butyl 4 methyl phenol mass ratio:(0.1-1).
Wherein in one embodiment, the diisocyanate is methyl diphenylene diisocyanate, toluene diisocynate
One or more of ester, IPDI and HDI.
Wherein in one embodiment, the solvent be ether solvent, one kind of lipid solvent and aromatic hydrocarbon solvent or
It is various.
Wherein in one embodiment, the epoxy resin is bisphenol A type epoxy resin, bisphenol f type epoxy resin, phenolic aldehyde
One or more in epoxy resin and o-cresol formaldehyde epoxy resin.
Wherein in one embodiment, the catalyst is N, N- dimethyl benzylamines, DMP-30, triethylamine, 2- methyl miaows
Azoles, 2-ethyl-4-methylimidazole, lithium chloride, aluminium chloride, zinc bromide, aluminium chloride-tetrahydrofuran, aluminium chloride-hexamethyl phosphinylidyne three
One or more in amine, aluminium chloride-triphenylphosphine oxide, magnesium chloride-HMPA and magnesium chloride-triphenylphosphine oxide.
In the present invention-monitoring of NCO group content determined by di-n-butylamine titrimetric standard.
The present invention is in preparation process by by diisocyanate, dibutyl tin laurate and the acrylic acid of pentaerythrite three
Ester is added separately in solvent, keeps 40 DEG C -70 DEG C of temperature to be reacted, when in system-content of NCO group is initially to contain
Stop reaction during the 48%-55% of amount, obtain the addition product of two isocyanic acid half；Again by epoxy resin, catalyst and the tertiary fourths of 2,6- bis-
Base -4- methylphenols are added separately in the addition product of two isocyanic acid half, and temperature is increased to 110 DEG C -140 DEG C and is reacted,
Until in system-NCO group disappearance, that is, the photocuring heat reactive resin of structure containing oxazolidone is obtained, through in monitoring infrared spectrum
Carbonyl is in 1750cm in Chu Xian oxazolidone structures-1The absworption peak at place.Photocuring heat reactive resin prepared by the method has excellent
Different heat resistance and preferable adhesive force.
A kind of photocuring heat reactive resin of structure containing oxazolidone, the knot containing oxazolidone as described in any of the above-described embodiment
The preparation method of structure photocuring heat reactive resin is prepared from.
The photocuring heat reactive resin prepared in the present invention is by the Yin Ru oxazolidones ring knot in epoxy molecule chain
Structure, from making system that there is excellent heat resistance and adhesive force.It is simultaneously acrylate-based containing epoxide group and multiple in the resin
Group, with photocuring heat curable properties, increased crosslink density, system heat resistance is further enhanced.
Additionally, it is necessary to provide a kind of photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone.
A kind of photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone, mainly including following quality
The component of percentage composition：
Wherein in one embodiment, the alkali soluble resins is carboxyl functional acrylic's resin, carboxylic poly- ammonia
Ester resin, anhydride modified epoxy acrylic resin, styrene maleic anhydride copolymer, phenol novolacs, alkylphenol phenolic aldehyde
One or more in resin and bisphenol A phenolic resin.
Wherein in one embodiment, the light trigger be 2- hydroxy-2-methyl -1- phenylacetones -1,2- methyl isophthalic acids -
(4- first mercaptophenyl) -2- morpholines acetone -1,2- phenyl -2- dimethylaminos -1- (4- morpholinyl phenyls)-butanone -1, isopropyl sulphur
Miscellaneous anthrone, 2,4- diethyl thioxanthones, 2,4,6- trimethylbenzoyls diphenyl phosphine oxide, double (2,4,6- trimethylbenzene first
Acyl group) phenyl phosphine oxide, double (2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) cyclopentadienyl titanium, 9- anthracene methyl Ns, N- diethylacbamazines
One or more in acid esters, 2- (3- benzoylphenyls) propionic acid guanidines and 1- (anthraquinone -2- bases) ethyl imidazol(e) carboxylate.
Wherein in one embodiment, the pigment is dark green, phthalocyanine blue, azophosphine, azophloxine, carbon black and titanium dioxide
In one or more.
Wherein in one embodiment, described filler is talcum powder, barium sulfate, silicon powder, bentonite, aerosil
With one or more in calcium carbonate.
Wherein in one embodiment, the solvent be binary acid methyl esters, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether,
One or more in dipropylene glycol methyl ether, 2-Butoxyethyl acetate, propylene glycol methyl ether acetate and aromatic hydrocarbon solvent.
Wherein in one embodiment, the thermosetting accelerator is dicyandiamide, melamine, glyoxaline compound, uncle
One or more in amine, tertiary ammonium salt, substitute urea compound, boron amide, boron amide salt and Boron Amine Complex
Wherein in one embodiment, the acrylic ester monomer be n-butyl acrylate, senecioate-hydroxyl ethyl ester,
The double acrylic acid of 2- benzene oxygen ethyl propylenes acid esters, iso-bornyl acrylate, 1,6-HD double methacrylate, two contracting propane diols
Ester, tripropylene glycol double methacrylate, Ethoxylated bisphenol A dimethylacrylates, the propylene of diethoxy neopentyl glycol two
Acid esters, ethoxylated neopentylglycol diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three
One or more in the propylene acid esters of (2- ethoxys) isocyanates three and double pentaerythritol methacrylate.
Photosensitive solder resist material in the present invention includes the photocuring heat reactive resin of Han oxazolidone ring structures, the photosensitive resistance
Wlding material has excellent heat resistance, adhesive force and endurance.The solder resist material as printed circuit board soldermask coatings when, it is right
The plain conductor surface of circuit board has preferable adhesive force, high temperature resistant and endurance performance, so as in printed circuit plate surface
Non-foaming stripping when lead-free tin spray is processed is carried out, the printed circuit board of better quality can be obtained.
Specific embodiment
Unless otherwise defined, all of technologies and scientific terms used here by the article with belong to technical field of the invention
The implication that technical staff is generally understood that is identical.The term for being used in the description of the invention herein is intended merely to description tool
The purpose of the embodiment of body, it is not intended that in the limitation present invention.Term as used herein "and/or" includes one or more phases
The arbitrary and all of combination of the Listed Items of pass.
In one implementation method, the preparation method of the photocuring heat reactive resin of Han oxazolidine ketone ring structures includes following step
Suddenly：
Diisocyanate, dibutyl tin laurate and pentaerythritol triacrylate are added separately to dibasic acid ester molten
In agent, 40 DEG C -70 DEG C of reaction temperature is kept, reaction a period of time, in reaction system is monitored-content of NCO group is first
Stop reaction during the 48%-50% of beginning content, obtain the addition product of two isocyanic acid half；
Epoxy resin, catalyst and 2,6 di tert butyl 4 methyl phenol are added separately to the addition of two isocyanic acid half
Thing, keep 110 DEG C -140 DEG C of reaction temperature, reaction a period of time, when in monitoring system-NCO group disappear when stop reaction,
After measured in infrared spectrum in Chu Xian oxazolidone ring structures carbonyl 1750cm-1The absworption peak at place, that is, obtain containing oxazolidone
Structure photocuring heat reactive resin.
Pentaerythritol triacrylate and the mol ratio of the diisocyanate are 1 in present embodiment:(1-1.05)；This two
Isocyanates is 100 with the mass ratio of the dibutyl tin laurate：(0.1-1)；The diisocyanate and the dibasic acid ester
Mass ratio is 1:(0.11-0.2)；In the epoxy resin epoxy group and the intermediate flux-mol ratio of NCO group is 1:
(0.5-0.8)；The epoxy resin is 100 with the mass ratio of the catalyst:(0.1-1)；The epoxy resin and the tertiary fourths of 2,6- bis-
Base -4- methylphenols mass ratio is 100:(0.1-1).
Diisocyanate is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), isophorone in present embodiment
One or more of diisocyanate and HDI.
Solvent is one or more in ethers, lipid and aromatic hydrocarbon solvent in present embodiment.Specifically, diethyl
Glycol monobutyl ether, diethylene glycol monoethyl ether, Dipropylene glycol mono-n-butyl Ether, DPE, diethylene glycol ether acetate alone,
Diethylene glycol monomethyl ether acetate, S150 solvents, one or more of S200 solvents.
Present embodiment epoxy resin be bisphenol A type epoxy resin, bisphenol f type epoxy resin, novolac epoxy resin and
One or more in o-cresol formaldehyde epoxy resin.
Catalyst is N, N- dimethyl benzylamines, DMP-30, triethylamine, 2-methylimidazole, 2- ethyls -4- in present embodiment
Methylimidazole, lithium chloride, aluminium chloride, zinc bromide, aluminium chloride-tetrahydrofuran, aluminium chloride-HMPA, aluminium chloride-three
One or more in phenyl phosphine oxide, magnesium chloride-HMPA and magnesium chloride-triphenylphosphine oxide.
By by diisocyanate, dibutyl tin laurate and the propylene of pentaerythrite three in preparation process in the present invention
Acid esters is added separately in dibasic acid ester solvent, keeps 40 DEG C -70 DEG C of temperature to be reacted,-NCO the bases in system is monitored
Stop reaction when the content of group is the 48%-55% of initial content, obtain the addition product of two isocyanic acid half；Again by epoxy resin, urge
Agent and 2,6- di-tert-butyl-4-methy phenol are added separately in the addition product of two isocyanic acid half, and temperature is increased to 110 DEG C -140
DEG C reacted, until in system-NCO group disappears, carbonyl exists in Chu Xian oxazolidone structures in infrared spectrum after measured
1750cm-1The absworption peak at place, that is, obtain the photocuring heat reactive resin of the ring of ketone containing oxazolidine.The light prepared in present embodiment
Solidification heat reactive resin has excellent heat resistance and preferable adhesive force.
In present embodiment-monitoring of NCO group content determined by di-n-butylamine titrimetric standard.
Using the photocuring heat reactive resin of above method preparation by epoxy molecule chain in one implementation method
Yin Ru oxazolidone ring structures, so that with excellent heat resistance and preferable adhesive force.It is simultaneously double containing carbon carbon in the resin
Key, epoxide group and multiple acrylate groups, with photocuring and heat curable properties, and increased crosslink density, and its is heat-resisting
Property is further enhanced.
Additionally, there is a need to providing a kind of photosensitive solder resist material of the photocuring of structure containing oxazolidone heat reactive resin.
In one embodiment, a kind of photosensitive solder resist material containing photocuring heat reactive resin, mainly including following matter
Measure the component of percentage composition：
Specifically, a kind of photosensitive solder resist material containing photocuring heat reactive resin, mainly contains including following quality percentage
The component of amount：
Alkali soluble resins is resin containing carboxyl functional acrylic, carboxylic polyurethane resin, acid in present embodiment
Anhydride modification epoxy acrylic resin, styrene maleic anhydride copolymer, phenol novolacs, alkylphenol phenolic resin and bis-phenol
One or more in A phenolic resin.
Light trigger, also known as sensitising agent or light curing agent, is that a class can be in ultraviolet region (250nm-420nm) or visible ray
Area (400nm-800nm) absorbs the energy of certain wavelength, free radical, cation, anion etc. is produced, so as to trigger monomer to be polymerized
The compound of crosslinking curing.Wherein, Photobase generator is that the light trigger of anion photocuring system is photograph of the class in ultraviolet light
Penetrate down the compound that can produce alkaline matter.It is appreciated that in other embodiments light trigger be 2- hydroxy-2-methyls-
1- phenylacetones -1,2- methyl isophthalic acids-(4- first mercaptophenyl) -2- morpholines acetone -1,2- phenyl -2- dimethylaminos -1- (4- morpholines
Phenyl)-butanone -1, isopropyl thioxanthone, 2,4- diethyl thioxanthones, 2,4,6- trimethylbenzoyls diphenyl oxidation
Phosphine, double (2,4,6- trimethylbenzoyls) phenyl phosphine oxides, double (2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) cyclopentadienyl titanium, 9-
Anthracene methyl N, N- diethylaminos formic acid esters, 2- (3- benzoylphenyls) propionic acid guanidines and 1- (anthraquinone -2- bases) ethyl imidazol(e) carboxylic
One or more in acid esters.
Solvent is binary acid methyl esters, ethylene glycol monobutyl ether, diethylene glycol monobutyl ether, dipropylene glycol methyl ether, butyl glycol ether
One or more in acetate, propylene glycol methyl ether acetate and aromatic hydrocarbon solvent.
Acrylic ester monomer is n-butyl acrylate, senecioate-hydroxyl ethyl ester, 2- benzene oxygen ethyl propylenes acid esters, different ice
Chip base acrylate, 1,6-HD double methacrylate, two contracting propane diols double methacrylates, tripropylene glycol double methacrylate,
Ethoxylated bisphenol A dimethylacrylates, diethoxy neopentylglycol diacrylate, ethoxylated neopentylglycol dipropyl
Olefin(e) acid ester, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three (2- ethoxys) acrylic acids of isocyanates three
One or more in ester and double pentaerythritol methacrylate.
In the present embodiment, also promote for filler, pigment and heat cure comprising filler, thermosetting accelerator and pigment
Enter agent to have no particular limits, as long as being adapted to the use of photosensitive solder resist material.Conventional filler has sulfuric acid dam, huge sum of money stone
Powder, silica flour, talcum powder, mica powder, gas-phase silica, clay, magnesium carbonate, calcium carbonate, aluminum oxide, aluminium hydroxide, kaolin,
Silicon powder, bentonite or aerosil etc..Conventional pigment has dark green, blue or green blue, titanium dioxide, carbon black, lithopone, idol
Nitrogen Huang, azophloxine, permanent violet, permanent yellow or ultramarine etc., above-mentioned pigment can be used alone, but also two or more mixing makes
With.Conventional thermosetting accelerator is epoxy resin thermosetting accelerator, including imidazoles, 2-methylimidazole, 2- ethyl imidazol(e)s, 2-
Ethyl -4- methyl-imidazoles, 2- phenylimidazoles, 4- phenylimidazoles, 1- amino-ethyl -2- phenylimidazoles, 1- (2- amino-ethyls) -
The imdazole derivatives such as 2-ethyl-4-methylimidazole；Dicyanodiamide, melamine, phenyl dimethyl amine, 4- (dimethylaminos
Base) amines such as-N, N- dimethyl benzyl amines；The hydrazide kind compounds such as AH, decanedioyl hydrazine；And the phosphine such as triphenylphosphine
Compound, tertiary amine, tertiary ammonium salt, substitute urea compound, boron amide, boron amide salt and Boron Amine Complex etc..Thermosetting accelerator is not special
The above compound is not defined in, as long as Epoxy cure catalysts, or promote epoxy radicals and complete base reaction
Material can be used in the present invention.Above-mentioned substance can be used alone, but also two or more is used in mixed way.
Specifically, filler is the one kind in talcum powder, barium sulfate, silicon powder, bentonite, aerosil and calcium carbonate
Or it is various.Pigment is one or more in dark green, phthalocyanine blue, azophosphine, azophloxine, carbon black and titanium dioxide.Heat cure promotees
Enter agent for dicyandiamide, melamine, glyoxaline compound, tertiary amine, tertiary ammonium salt, substitute urea compound, boron amide, boron amide salt and boron
One or more in amine complex.
Present embodiment can mix by by above-mentioned component, and acquisition photosensitive solder resist material is ground in milling apparatus.Tool
Body ground, is easy to assist side surface to be coated with the photosensitive solder resist material use organic solvent adjustment viscosity of present embodiment.More
Body ground, above-mentioned component is well mixed, and fineness is ground to less than 15 μm with three-roller, and sticking to 150dpas with dibasic acid ester tune obtains
The photosensitive solder resist material of coating must be adapted to.
Photosensitive solder resist material in the present invention includes Han oxazolidone ring structure photocuring heat reactive resins.The photosensitive solder resist
Material has excellent heat resistance, adhesive force and endurance, the solder resist material as printed circuit board soldermask coatings when, to electricity
The plain conductor surface of road plate has preferable adhesive force, high temperature resistant and endurance performance, so as to enter in printed circuit plate surface
Non-foaming stripping during the treatment of row lead-free tin spray, can obtain the printed circuit board of better quality.
Additionally, there is a need to the photosensitive solder resist material provided Han oxazolidone ring structure photocuring heat reactive resins are included
It is used for the purposes of printed circuit board in soldermask coatings form.Specifically, including Han oxazolidone ring structure photocuring heat cure trees
The photosensitive solder resist material of fat is coated on circuit board through screen printing mode, through low temperature is pre-baked, exposure, development, bake after high temperature after
The soldermask coatings are obtained.
Additionally, there is a need to a kind of printed circuit board of offer, it includes Han oxazolidone ring structure photocuring heat cure trees
The photosensitive solder resist material of fat is used as soldermask coatings.
It is below specific embodiment part：
Embodiment 1：The preparation of the photocuring heat reactive resin of structure containing oxazolidone A
257.8g methyl diphenylene diisocyanates, 0.8g dibutyl tin laurates are added separately to 36g S150 virtues
In hydrocarbon solvent, 298.3g pentaerythritol triacrylates are added dropwise, keep reaction temperature at 40-70 DEG C, react 2-4h.When monitoring
In system-content of NCO group for initial content 50% when stop reaction, obtain the addition product of two isocyanic acid half, be cooled to room
Temperature.By 360g novolac epoxy resins (NPPN-638S), 0.7gN, N- dimethyl benzylamines, 0.5g 2,6- di-t-butyl -4- methyl
Phenol is added in the gained addition product of two isocyanic acid half, is heated to 130 DEG C, when in monitoring system-NCO group disappear when stop it is anti-
Should, IR measure is carried out to product after reaction, the suction in infrared spectrum in Chu Xian oxazolidone ring structures at the 1750cm-1 of carbonyl
Peak is received, the photocuring heat reactive resin A of Han oxazolidone ring structures is obtained final product.
Embodiment 2：The preparation of the photocuring heat reactive resin of structure containing oxazolidone B
257.8g methyl diphenylene diisocyanates, 0.8g dibutyl tin laurates are added separately to 36g S150 virtues
In hydrocarbon solvent solvent, 298.3g pentaerythritol triacrylates are added dropwise, keep reaction temperature at 40-70 DEG C, react 2-4h.Work as prison
In measuring system-content of NCO group for initial content 50% when stop reaction, obtain the addition product of two isocyanic acid half, cool down
To room temperature.By 276.9g novolac epoxy resins (NPPN-638S), 0.7gN, N- dimethyl benzylamines, 0.5g2,6- di-t-butyls -4-
Methylphenol add gained the addition product of two isocyanic acid half in, be heated to 130 DEG C, when in monitoring system-NCO group disappear when stop
Only react, IR measure is carried out to product after reaction, in infrared spectrum in Chu Xian oxazolidone ring structures at the 1750cm-1 of carbonyl
Absworption peak, obtain final product the photocuring heat reactive resin B of Han oxazolidone ring structures.
Embodiment 3：The preparation of the photocuring heat reactive resin of structure containing oxazolidone C
257.8g methyl diphenylene diisocyanates, 0.8g dibutyl tin laurates are added separately to 36gS150 virtues
In hydrocarbon solvent solvent, 298.3g pentaerythritol triacrylates are added dropwise, keep reaction temperature at 40-70 DEG C, react 2-4h.Work as prison
In measuring reaction system-content of NCO group for initial content 50% when stop reaction, obtain the addition product of two isocyanic acid half,
It is cooled to room temperature.By 225g novolac epoxy resins (NPPN-638S), 0.7gN, N- dimethyl benzylamines, 0.5g2,6- di-t-butyls-
4- methylphenols are added in the gained addition product of two isocyanic acid half, are heated to 130 DEG C, in reaction system is monitored-NCO group disappears
Stop reaction during mistake, IR measure is carried out to product after reaction, carbonyl in Chu Xian oxazolidone ring structures in infrared spectrum
Absworption peak at 1750cm-1, obtains final product the photocuring heat reactive resin C of Han oxazolidine ketone ring structures.
Embodiment 4：The preparation of the photosensitive solder resist material containing photocuring heat reactive resin
Each component is configured to photosensitive solder resist composition, i.e. photosensitive solder resist material by the weight/mass percentage composition that table 1 is listed.By table
1 each component listed is well mixed, and fineness is ground to less than 15 μm with three-roll grinder, is adjusted with dibasic acid ester and sticked to
150dpa.s, that is, be obtained photosensitive solder resist material.The photosensitive solder resist material is incited somebody to action by 43T silk-screen printings on circuit board surface
The circuit board for printing is placed in constant temperature drying box in 75 DEG C of pre-baked a period of times, then exposes (21 grades of exposures with ultraviolet photoetching machine
Chi, 10 grades of residual films), with 1 ± 0.2% sodium carbonate liquor in 30 ± 1 DEG C of development 60s of temperature, model is put into 150 DEG C of constant temperature roasters
Middle baking 1h.Photosensitive solder resist material developability on circuit boards, adhesive force, heat resistance, acid resistance, alkali resistance are surveyed
Examination is evaluated.
Table 1
Note 1：CCR-4959HW, chemical drug chemical industry (Wuxi) Co., Ltd.
Note 2：JRCURE-1107 (the general trade mark 907), Tianjin Jiu new materials limited company.
Note 3：JRCURE-1107 (the general trade mark 907), Tianjin Jiu new materials limited company.
Note 4：Dark green K8730, German BASF.
Note 5：Barium sulfate, AY-JB53, Fushan Anyi Nano Materials Co., Ltd.
Note 6：Dibasic acid ester, English Weida.
Note 7：DPHA, EM264, Changxing chemical industry.
Note 8：Dicyandiamide, OMICURE DDA5, U.S. CVC.
Note 9：NPPN-638S, Nanya Plastic Cement Industry Co., Ltd.
The performance test evaluation criterion of photosensitive solder resist material is as follows：
(1) developability
Whether observed by printed plate 75 DEG C of difference pre-baked 45,55,65,75min, after development on base material has residual.Without residual
It is qualified to be left, and it is unqualified to have residual.
(2) adhesive force
With reference to GB/T9286-1998《The lattice of drawing of paint and varnish paint film are tested》.Coating without coming off for qualified, have come off for
It is unqualified.
(3) heat resistance
Circuit board surface of the high temperature after roasting is coated with rosin flux, 288 ± 5 DEG C × 10s × 3 time of wicking.Use 3M adhesive tapes
(600 type) is pullled 3 times, and observation coating whether there is foaming is fallen oil.Coating is qualified without oil is fallen, and it is unqualified to have oil.
(4) acid resistance
Circuit board of the high temperature after roasting is immersed in H2SO4 solution (25 ± 1 DEG C) 30min of 10% volume fraction, clear water is used
Cleaning, drying.Pullled 3 times with 3M adhesive tapes (600 type), observation coating whether there is oil.Coating is qualified without oil is fallen, and has oil for not
It is qualified.
(5) alkali resistance
Circuit board of the high temperature after roasting is immersed in NaOH solution (25 ± 1 DEG C) 30min of 10% mass fraction, is washed with clear water
Only, dry.Pullled 3 times with 3M adhesive tapes (600 type), observation coating whether there is oil.Coating is qualified without oil is fallen, and has oil not conform to
Lattice.
Table 2
Known by table 2, the photosensitive solder resist material prepared by the photocuring heat reactive resin containing oxazolidone structure in the present embodiment
1st, the 2 photosensitive solder resist material control groups prepared with the novolac epoxy resin of non-Han oxazolidones ring structure are compared, and are both had
Excellent developability and preferably adhesive force, acid resistance and alkali resistance, but by the photocuring heat cure of Han oxazolidine ketone structures
The standby photosensitive solder resist material of resin-made has more excellent heat resistance.The heat resistance of photosensitive solder resist material 3 and alkali resistance be not good be by
It is relatively low in resin C epoxy group mass contgs, so that the carboxyl of alkali soluble type resin can not fully participate in cross-linking reaction, system after solidification
In remain carboxyl, crosslink density declines.
Each technical characteristic of the embodiment can be combined arbitrarily above, to make description succinct, not to above-mentioned implementation
The all possible combination of each technical characteristic in example is all described, as long as however, the combination of these technical characteristics does not exist
Contradiction, is all considered to be the scope of this specification record.
The embodiment only expresses several embodiments of the invention above, and its description is more specific and detailed, but not
Can therefore be construed as limiting the scope of the patent.It should be pointed out that for the person of ordinary skill of the art,
Without departing from the inventive concept of the premise, various modifications and improvements can be made, these belong to protection model of the invention
Enclose.Therefore, the protection domain of patent of the present invention should be determined by the appended claims.
Claims (10)
1. a kind of preparation method of the photocuring of structure containing oxazolidone heat reactive resin, it is characterised in that the preparation method bag
Include following steps：
Diisocyanate, dibutyl tin laurate and pentaerythritol triacrylate are added separately in solvent, keep anti-
40 DEG C -70 DEG C of temperature is answered, in monitoring system-change in concentration of NCO group, when the content of-NCO group is initial content
Stop reaction during 48%-55%, obtain the addition product of diisocyanate half；
Epoxy resin, catalyst and 2,6 di tert butyl 4 methyl phenol are added separately to the addition of the diisocyanate half
In thing, keep 110 DEG C -140 DEG C of reaction temperature, when in system-content of NCO group be 0 when stop reaction, that is, obtain containing oxazole
Alkanone structure photocuring heat reactive resin.
2. the preparation method of the photocuring of structure containing oxazolidone heat reactive resin according to claim 1, it is characterised in that
The pentaerythritol triacrylate is 1 with the mol ratio of the diisocyanate:(1-1.05)；The diisocyanate and institute
The mass ratio for stating dibutyl tin laurate is 100：(0.1-1)；The mass ratio of the diisocyanate and the dibasic acid ester
It is 1:(0.11-0.2)；In the epoxy resin epoxide epoxy group group and the intermediate flux-mol ratio of NCO group is 1:
(0.5-0.8)；The epoxy resin is 100 with the mass ratio of the catalyst:(0.1-1)；The epoxy resin and described 2,
6- di-tert-butyl-4-methy phenols mass ratio is 100:(0.1-1).
3. the preparation method of the photocuring of structure containing oxazolidone heat reactive resin according to claim 1 and 2, its feature exists
In the diisocyanate is methyl diphenylene diisocyanate, toluene di-isocyanate(TDI), IPDI and six
One or more of methylene diisocyanate.
4. the preparation method of the photocuring of structure containing oxazolidone heat reactive resin according to claim 1 and 2, its feature exists
In the solvent is one or more of ether solvent, lipid solvent and aromatic hydrocarbon solvent；The catalyst is N, N- diformazans
Base benzylamine, DMP-30, triethylamine, 2-methylimidazole, 2-ethyl-4-methylimidazole, lithium chloride, aluminium chloride, zinc bromide, chlorination
Aluminium-tetrahydrofuran, aluminium chloride-HMPA, aluminium chloride-triphenylphosphine oxide, magnesium chloride-HMPA and chlorine
Change one or more in magnesium-triphenylphosphine oxide.
5. the preparation method of the photocuring of structure containing oxazolidone heat reactive resin according to claim 1 and 2, its feature exists
In the epoxy resin is bisphenol A type epoxy resin, bisphenol f type epoxy resin, novolac epoxy resin and o-cresol formaldehyde asphalt mixtures modified by epoxy resin
One or more in fat.
6. a kind of photocuring heat reactive resin of structure containing oxazolidone, it is characterised in that as described in claim any one of 1-5
The preparation method of the photocuring heat reactive resin of structure containing oxazolidone is prepared from.
7. a kind of photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone, it is characterised in that the sense
Light solder resist material mainly includes the component of following weight/mass percentage composition：
8. the photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone according to claim 7, its
It is characterised by, the alkali soluble resins is carboxyl functional acrylic's resin, carboxylic polyurethane resin, anhydride modified epoxy
Acrylic resin, styrene maleic anhydride copolymer, phenol novolacs, alkylphenol phenolic resin and bisphenol A phenolic resin
In one or more.
9. the photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone according to claim 7, its
It is characterised by, the light trigger is 2- hydroxy-2-methyl -1- phenylacetones -1,2- methyl isophthalic acids-(4- first mercaptophenyl) -2-
Morpholine acetone -1,2- phenyl -2- dimethylaminos -1- (4- morpholinyl phenyls)-butanone -1, isopropyl thioxanthone, 2,4- diethyl
It is thioxanthone, 2,4,6- trimethylbenzoyls diphenyl phosphine oxide, double (2,4,6- trimethylbenzoyls) phenyl phosphine oxides, double
(2,6- bis- fluoro- 3- (1H- pyrrole radicals -1) phenyl) cyclopentadienyl titanium, 9- anthracene methyl Ns, N- diethylaminos formic acid esters, 2- (3- benzoyls
Phenyl) one or more in propionic acid guanidine and 1- (anthraquinone -2- bases) ethyl imidazol(e) carboxylate, the hot thermosetting accelerator is double
Cyanamide, melamine, glyoxaline compound, tertiary amine, tertiary ammonium salt, substitute urea compound, boron amide, boron amide salt and Boron Amine Complex
In one or more.
10. the photosensitive solder resist material including the photocuring heat reactive resin of structure containing oxazolidone according to claim 7, its
Be characterised by, the acrylic ester monomer be n-butyl acrylate, senecioate-hydroxyl ethyl ester, 2- benzene oxygen ethyl propylenes acid esters,
The double acrylic acid of iso-bornyl acrylate, 1,6-HD double methacrylate, two contracting propane diols double methacrylates, tripropylene glycol
Ester, Ethoxylated bisphenol A dimethylacrylates, diethoxy neopentylglycol diacrylate, ethoxylated neopentylglycol
Diacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, three (2- ethoxys) isocyanates 3 third
One or more in diluted acid ester and double pentaerythritol methacrylate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710087190.9A CN106832221B (en) | 2017-02-17 | 2017-02-17 | The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201710087190.9A CN106832221B (en) | 2017-02-17 | 2017-02-17 | The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN106832221A true CN106832221A (en) | 2017-06-13 |
| CN106832221B CN106832221B (en) | 2017-12-29 |
Family
ID=59129162
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201710087190.9A Active CN106832221B (en) | 2017-02-17 | 2017-02-17 | The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN106832221B (en) |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108341921A (en) * | 2018-03-27 | 2018-07-31 | 佛山市三求光固材料股份有限公司 | Polyurethane-modified flexible epoxy acrylic resin, preparation method, photocuring marking ink and flexible circuit board |
| CN108976381A (en) * | 2018-08-22 | 2018-12-11 | 广东昊辉新材料有限公司 | Epoxy modified polyurethane acrylate aqueous dispersion and preparation method thereof |
| CN109160997A (en) * | 2018-08-28 | 2019-01-08 | 佛山市三求光固材料股份有限公司 | Alkali solubility UV-cured resin, preparation method containing urethano and the ultraviolet light solidification etch-resistant material containing it |
| CN109280367A (en) * | 2018-09-17 | 2019-01-29 | 佛山朝鸿新材料科技有限公司 | A kind of fire-retardant toughened plastic material and preparation method thereof |
| CN113388059A (en) * | 2021-06-21 | 2021-09-14 | 深圳职业技术学院 | High-refractive-index photocuring resin composition with oxazolidinone structure, preparation method thereof, and thiophenyl ether photosensitive monomer and intermediate thereof |
| CN115185159A (en) * | 2021-09-17 | 2022-10-14 | 广东硕成科技股份有限公司 | A kind of solder resist dry film and preparation method thereof |
| CN115612096A (en) * | 2022-11-02 | 2023-01-17 | 广州市嵩达新材料科技有限公司 | Polyoxazolidinone prepolymer and preparation method and application thereof |
| CN118027806A (en) * | 2024-02-01 | 2024-05-14 | 江苏大自然智能家居有限公司 | Water-based UV (ultraviolet) photo-curing coating for wood floor and preparation method thereof |
| CN119529621A (en) * | 2024-11-27 | 2025-02-28 | 迪克印材（江门）有限公司 | A high temperature resistant waterproof coating and preparation method thereof |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101899127A (en) * | 2009-06-01 | 2010-12-01 | 钟文军 | Polyurethane modified acrylic resin and preparation method thereof |
| CN101928380A (en) * | 2009-06-18 | 2010-12-29 | 新亚T&C | Method for preparing flame-retardant polyepoxy compound |
| US20120095132A1 (en) * | 2010-10-19 | 2012-04-19 | Chung-Hao Chang | Halogen- and phosphorus-free thermosetting resin composition |
| CN105467762A (en) * | 2014-09-30 | 2016-04-06 | 太阳油墨制造株式会社 | Curing resin composition, dried film and cured material thereof, and printed circuit board with same |
| CN105968321A (en) * | 2015-03-13 | 2016-09-28 | 新日铁住金化学株式会社 | Oxazolidone ring-containing epoxy resin, method for producing the thereof, epoxy resin composition, cured product and application thereof |
-
2017
- 2017-02-17 CN CN201710087190.9A patent/CN106832221B/en active Active
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101899127A (en) * | 2009-06-01 | 2010-12-01 | 钟文军 | Polyurethane modified acrylic resin and preparation method thereof |
| CN101928380A (en) * | 2009-06-18 | 2010-12-29 | 新亚T&C | Method for preparing flame-retardant polyepoxy compound |
| US20120095132A1 (en) * | 2010-10-19 | 2012-04-19 | Chung-Hao Chang | Halogen- and phosphorus-free thermosetting resin composition |
| CN105467762A (en) * | 2014-09-30 | 2016-04-06 | 太阳油墨制造株式会社 | Curing resin composition, dried film and cured material thereof, and printed circuit board with same |
| CN105968321A (en) * | 2015-03-13 | 2016-09-28 | 新日铁住金化学株式会社 | Oxazolidone ring-containing epoxy resin, method for producing the thereof, epoxy resin composition, cured product and application thereof |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108341921A (en) * | 2018-03-27 | 2018-07-31 | 佛山市三求光固材料股份有限公司 | Polyurethane-modified flexible epoxy acrylic resin, preparation method, photocuring marking ink and flexible circuit board |
| CN108341921B (en) * | 2018-03-27 | 2020-01-21 | 广东三求光固材料股份有限公司 | Polyurethane modified flexible epoxy acrylic resin, preparation method thereof, photocuring identification ink and flexible printed circuit board |
| CN108976381B (en) * | 2018-08-22 | 2020-12-18 | 广东昊辉新材料有限公司 | A kind of epoxy modified polyurethane acrylate water dispersion and preparation method thereof |
| CN108976381A (en) * | 2018-08-22 | 2018-12-11 | 广东昊辉新材料有限公司 | Epoxy modified polyurethane acrylate aqueous dispersion and preparation method thereof |
| CN109160997A (en) * | 2018-08-28 | 2019-01-08 | 佛山市三求光固材料股份有限公司 | Alkali solubility UV-cured resin, preparation method containing urethano and the ultraviolet light solidification etch-resistant material containing it |
| CN109160997B (en) * | 2018-08-28 | 2019-11-19 | 广东三求光固材料股份有限公司 | Alkali solubility UV-cured resin, preparation method containing urethano and the ultraviolet light solidification etch-resistant material containing it |
| CN109280367A (en) * | 2018-09-17 | 2019-01-29 | 佛山朝鸿新材料科技有限公司 | A kind of fire-retardant toughened plastic material and preparation method thereof |
| CN113388059A (en) * | 2021-06-21 | 2021-09-14 | 深圳职业技术学院 | High-refractive-index photocuring resin composition with oxazolidinone structure, preparation method thereof, and thiophenyl ether photosensitive monomer and intermediate thereof |
| CN115185159A (en) * | 2021-09-17 | 2022-10-14 | 广东硕成科技股份有限公司 | A kind of solder resist dry film and preparation method thereof |
| CN115185159B (en) * | 2021-09-17 | 2025-09-05 | 广东硕成科技股份有限公司 | A solder resist dry film and preparation method thereof |
| CN115612096A (en) * | 2022-11-02 | 2023-01-17 | 广州市嵩达新材料科技有限公司 | Polyoxazolidinone prepolymer and preparation method and application thereof |
| CN118027806A (en) * | 2024-02-01 | 2024-05-14 | 江苏大自然智能家居有限公司 | Water-based UV (ultraviolet) photo-curing coating for wood floor and preparation method thereof |
| CN119529621A (en) * | 2024-11-27 | 2025-02-28 | 迪克印材（江门）有限公司 | A high temperature resistant waterproof coating and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| CN106832221B (en) | 2017-12-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN106832221B (en) | The photocuring of structure containing oxazolidone heat reactive resin, its preparation method and the photosensitive solder resist material containing it | |
| JP6047666B2 (en) | Method for producing dry film solder resist and film laminate used therefor | |
| US6475701B2 (en) | Active energy beam curable composition and printed wiring board | |
| CN1661475B (en) | Photocurable and thermosetting resin composition and printed wiring board using same | |
| CN109073969A (en) | Hardening resin composition, dry film, solidfied material and printed circuit board | |
| CN112034680A (en) | Curable resin composition, dry film, cured product and printed circuit board | |
| CN104350421B (en) | Photosensitive composition and printed circuit board having its cured layer | |
| CN102385244A (en) | Black curable resin composition | |
| CN108885400A (en) | Hardening resin composition, dry film, solidfied material and printed circuit board | |
| US20090101394A1 (en) | Photosensitive resin composition and flexible printed wiring circut board having insulative cover layer formed of photosensitive resin composition | |
| JP2018173609A (en) | Curable resin composition, dry film, cured product, and printed wiring board | |
| JPWO2018143220A1 (en) | Photocurable resin composition, dry film, cured product, and printed wiring board | |
| TW201942242A (en) | Curable resin composition, dry film, cured product, and printed circuit board suitable for being used in a printed circuit board and excellent in reliability and adhesion | |
| WO2021210570A1 (en) | Curable resin composition, dry film, cured article, and printed wiring board | |
| JP2019178307A (en) | Curable resin composition, dry film, cured product and electronic component | |
| CA2017860C (en) | Photoimageable compositions | |
| JP3849637B2 (en) | Photosensitive resin composition | |
| CN105086605B (en) | A kind of photocuring heat-curing composition ink, purposes and the wiring board containing it | |
| JP2022155116A (en) | Photosensitive resin composition, dry film, cured product, and electronic component | |
| JP4725833B2 (en) | Active energy ray-curable epoxy acrylate resin composition and cured product thereof | |
| JP3415779B2 (en) | Photosensitive resin composition | |
| TW202035595A (en) | Curable resin composition, dry film, cured product, and electronic component | |
| JPH0777800A (en) | Photosensitive resin composition | |
| US10423069B2 (en) | Water soluble photosensitive resin composition and film using same | |
| JPS62226145A (en) | Solder resist |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PB01 | Publication | ||
| PB01 | Publication | ||
| SE01 | Entry into force of request for substantive examination | ||
| SE01 | Entry into force of request for substantive examination | ||
| GR01 | Patent grant | ||
| GR01 | Patent grant | ||
| CP03 | Change of name, title or address |
Address after: 528000 No. 11, No. 26, Floro Road, Chancheng District, Foshan City, Guangdong Province Patentee after: Guangdong Sanqiu Optical Solid Materials Co., Ltd. Address before: 528000 No. 26, Floro Road, Chancheng District, Foshan City, Guangdong Province Patentee before: FOSHAN SQ UV CURING MATERIALS CO., LTD. |
|
| CP03 | Change of name, title or address | ||
| CP02 | Change in the address of a patent holder |
Address after: No. 8, Dehua Road, industrial park, Chengdong neighborhood committee, Decheng street, Deqing County, Zhaoqing City, Guangdong Province, 526699 Patentee after: Guangdong Sanqiu Optical Solid Materials Co.,Ltd. Address before: 528000 No. 11, No. 26, Floro Road, Chancheng District, Foshan City, Guangdong Province Patentee before: Guangdong Sanqiu Optical Solid Materials Co.,Ltd. |
|
| CP02 | Change in the address of a patent holder |