CN107300830A - A kind of new Photocurable composition and its application - Google Patents
A kind of new Photocurable composition and its application Download PDFInfo
- Publication number
- CN107300830A CN107300830A CN201610235085.0A CN201610235085A CN107300830A CN 107300830 A CN107300830 A CN 107300830A CN 201610235085 A CN201610235085 A CN 201610235085A CN 107300830 A CN107300830 A CN 107300830A
- Authority
- CN
- China
- Prior art keywords
- alkyl
- cycloalkyl
- compound
- photocurable composition
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 60
- 150000001875 compounds Chemical class 0.000 claims abstract description 68
- 238000000016 photochemical curing Methods 0.000 claims abstract description 22
- 150000003254 radicals Chemical class 0.000 claims abstract description 22
- 239000000463 material Substances 0.000 claims abstract description 19
- 239000004593 Epoxy Substances 0.000 claims abstract description 18
- 238000001723 curing Methods 0.000 claims abstract description 14
- 230000004044 response Effects 0.000 claims abstract description 14
- 150000001454 anthracenes Chemical class 0.000 claims abstract description 9
- 229920002521 macromolecule Polymers 0.000 claims abstract description 7
- 125000002091 cationic group Chemical group 0.000 claims abstract description 6
- -1 Hydrogen Chemical class 0.000 claims description 72
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 37
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 29
- 229910052739 hydrogen Inorganic materials 0.000 claims description 25
- 229910052736 halogen Inorganic materials 0.000 claims description 24
- 150000002367 halogens Chemical class 0.000 claims description 24
- 239000001257 hydrogen Substances 0.000 claims description 24
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- 239000003822 epoxy resin Substances 0.000 claims description 15
- 229920000647 polyepoxide Polymers 0.000 claims description 15
- 125000005120 alkyl cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 14
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 14
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 13
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 claims description 12
- 229940052303 ethers for general anesthesia Drugs 0.000 claims description 12
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 10
- 150000003839 salts Chemical class 0.000 claims description 10
- 125000004185 ester group Chemical group 0.000 claims description 8
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 239000011248 coating agent Substances 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 239000000976 ink Substances 0.000 claims description 6
- 229910052740 iodine Inorganic materials 0.000 claims description 6
- 239000011630 iodine Substances 0.000 claims description 6
- 239000003973 paint Substances 0.000 claims description 6
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- 150000005846 sugar alcohols Polymers 0.000 claims description 6
- 125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 5
- 238000003848 UV Light-Curing Methods 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 5
- 239000001273 butane Substances 0.000 claims description 5
- 239000012952 cationic photoinitiator Substances 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 125000000623 heterocyclic group Chemical group 0.000 claims description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 5
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 claims description 5
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims description 5
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 claims description 4
- 125000005250 alkyl acrylate group Chemical group 0.000 claims description 4
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 4
- 239000012965 benzophenone Substances 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 150000001768 cations Chemical class 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 3
- CTKINSOISVBQLD-UHFFFAOYSA-N Glycidol Chemical compound OCC1CO1 CTKINSOISVBQLD-UHFFFAOYSA-N 0.000 claims description 3
- 150000001336 alkenes Chemical class 0.000 claims description 3
- 125000003118 aryl group Chemical group 0.000 claims description 3
- 239000012954 diazonium Substances 0.000 claims description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 claims description 3
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 claims description 3
- 229920000728 polyester Polymers 0.000 claims description 3
- 125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 2
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
- HMBNQNDUEFFFNZ-UHFFFAOYSA-N 4-ethenoxybutan-1-ol Chemical class OCCCCOC=C HMBNQNDUEFFFNZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000003860 C1-C20 alkoxy group Chemical group 0.000 claims description 2
- 125000004648 C2-C8 alkenyl group Chemical group 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229910016861 F9SO3 Inorganic materials 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical class [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000005577 anthracene group Chemical group 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 229960000834 vinyl ether Drugs 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 3
- ZXHDVRATSGZISC-UHFFFAOYSA-N 1,2-bis(ethenoxy)ethane Chemical compound C=COCCOC=C ZXHDVRATSGZISC-UHFFFAOYSA-N 0.000 claims 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims 1
- 239000004845 glycidylamine epoxy resin Substances 0.000 claims 1
- 125000001188 haloalkyl group Chemical group 0.000 claims 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 claims 1
- 239000003999 initiator Substances 0.000 claims 1
- 150000002924 oxiranes Chemical group 0.000 claims 1
- FGIUAXJPYTZDNR-UHFFFAOYSA-N potassium nitrate Chemical compound [K+].[O-][N+]([O-])=O FGIUAXJPYTZDNR-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 abstract description 10
- 238000007711 solidification Methods 0.000 abstract description 10
- 230000008023 solidification Effects 0.000 abstract description 10
- 230000001070 adhesive effect Effects 0.000 abstract description 9
- 238000005457 optimization Methods 0.000 abstract description 3
- 230000000694 effects Effects 0.000 description 9
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 8
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 7
- 238000005516 engineering process Methods 0.000 description 6
- 238000011156 evaluation Methods 0.000 description 6
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 6
- 229910052753 mercury Inorganic materials 0.000 description 6
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 5
- 206010040844 Skin exfoliation Diseases 0.000 description 5
- 230000008859 change Effects 0.000 description 5
- 238000006757 chemical reactions by type Methods 0.000 description 5
- 238000007348 radical reaction Methods 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000000758 substrate Substances 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 230000007547 defect Effects 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 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
- 239000004925 Acrylic resin Substances 0.000 description 2
- 125000003358 C2-C20 alkenyl group Chemical group 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- 150000001335 aliphatic alkanes Chemical class 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 230000018109 developmental process Effects 0.000 description 2
- 239000012776 electronic material Substances 0.000 description 2
- 150000002118 epoxides Chemical group 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229920002120 photoresistant polymer Polymers 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 238000012827 research and development Methods 0.000 description 2
- 238000007761 roller coating Methods 0.000 description 2
- 238000006467 substitution reaction Methods 0.000 description 2
- UNMJLQGKEDTEKJ-UHFFFAOYSA-N (3-ethyloxetan-3-yl)methanol Chemical class CCC1(CO)COC1 UNMJLQGKEDTEKJ-UHFFFAOYSA-N 0.000 description 1
- NLQMSBJFLQPLIJ-UHFFFAOYSA-N (3-methyloxetan-3-yl)methanol Chemical class OCC1(C)COC1 NLQMSBJFLQPLIJ-UHFFFAOYSA-N 0.000 description 1
- SYEWHONLFGZGLK-UHFFFAOYSA-N 2-[1,3-bis(oxiran-2-ylmethoxy)propan-2-yloxymethyl]oxirane Chemical compound C1OC1COCC(OCC1OC1)COCC1CO1 SYEWHONLFGZGLK-UHFFFAOYSA-N 0.000 description 1
- 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 1
- AOBIOSPNXBMOAT-UHFFFAOYSA-N 2-[2-(oxiran-2-ylmethoxy)ethoxymethyl]oxirane Chemical compound C1OC1COCCOCC1CO1 AOBIOSPNXBMOAT-UHFFFAOYSA-N 0.000 description 1
- FZIIBDOXPQOKBP-UHFFFAOYSA-N 2-methyloxetane Chemical class CC1CCO1 FZIIBDOXPQOKBP-UHFFFAOYSA-N 0.000 description 1
- SLJFKNONPLNAPF-UHFFFAOYSA-N 3-Vinyl-7-oxabicyclo[4.1.0]heptane Chemical class C1C(C=C)CCC2OC21 SLJFKNONPLNAPF-UHFFFAOYSA-N 0.000 description 1
- 238000010146 3D printing Methods 0.000 description 1
- UYCGHYYLNBVUGK-UHFFFAOYSA-N 4-(ethenoxymethyl)-1,3-dioxolan-2-one Chemical class C=COCC1COC(=O)O1 UYCGHYYLNBVUGK-UHFFFAOYSA-N 0.000 description 1
- KBIWNQVZKHSHTI-UHFFFAOYSA-N 4-n,4-n-dimethylbenzene-1,4-diamine;oxalic acid Chemical compound OC(=O)C(O)=O.CN(C)C1=CC=C(N)C=C1 KBIWNQVZKHSHTI-UHFFFAOYSA-N 0.000 description 1
- OXQXGKNECHBVMO-UHFFFAOYSA-N 7-oxabicyclo[4.1.0]heptane-4-carboxylic acid Chemical class C1C(C(=O)O)CCC2OC21 OXQXGKNECHBVMO-UHFFFAOYSA-N 0.000 description 1
- 241001614291 Anoplistes Species 0.000 description 1
- GXGJIOMUZAGVEH-UHFFFAOYSA-N Chamazulene Chemical group CCC1=CC=C(C)C2=CC=C(C)C2=C1 GXGJIOMUZAGVEH-UHFFFAOYSA-N 0.000 description 1
- PMPVIKIVABFJJI-UHFFFAOYSA-N Cyclobutane Chemical compound C1CCC1 PMPVIKIVABFJJI-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-N Formic acid Chemical class OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 1
- 239000012901 Milli-Q water Substances 0.000 description 1
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Natural products OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 1
- 150000008062 acetophenones Chemical class 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 239000002390 adhesive tape Substances 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 230000004888 barrier function Effects 0.000 description 1
- WURBFLDFSFBTLW-UHFFFAOYSA-N benzil Chemical class C=1C=CC=CC=1C(=O)C(=O)C1=CC=CC=C1 WURBFLDFSFBTLW-UHFFFAOYSA-N 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical class C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012663 cationic photopolymerization Methods 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000013016 damping Methods 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [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])* 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000007641 inkjet printing Methods 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 238000007645 offset printing Methods 0.000 description 1
- 239000013307 optical fiber Substances 0.000 description 1
- 150000002921 oxetanes Chemical class 0.000 description 1
- 238000011056 performance test Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical class CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 239000011253 protective coating Substances 0.000 description 1
- 238000007650 screen-printing Methods 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 239000004065 semiconductor Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 229920002803 thermoplastic polyurethane Polymers 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 230000001960 triggered effect Effects 0.000 description 1
- 239000002966 varnish Substances 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N vinyl-ethylene Natural products C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/027—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds
- G03F7/028—Non-macromolecular photopolymerisable compounds having carbon-to-carbon double bonds, e.g. ethylenic compounds with photosensitivity-increasing substances, e.g. photoinitiators
- G03F7/031—Organic compounds not covered by group G03F7/029
-
- 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
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Epoxy Resins (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerisation Methods In General (AREA)
Abstract
The present invention discloses a kind of new Photocurable composition, comprising：Anthracene esters sensitizer, selected from the compound of structure shown in formula (I) and/or using formula (I) compound as the macromolecular compound of primary structure；Response type compound, including at least one compound containing unsaturated double-bond and/or at least one contain epoxy compounds；Light trigger.By compositional selecting and optimization, said composition is applicable to free radical type, cationic and mixes type photocuring system, has splendid response to the light source in 200 500nm wave-length coverages, curing rate is fast, developability and pattern integrity are good, and solidification film hardness is high, and the adhesive force on base material is strong.
Description
Technical field
The invention belongs to organic curing field, and in particular to a kind of new Photocurable composition and its in curing field
In application.
Background technology
UV-curing technology has application widely in fields such as electronic material preparations, according to Initiating polymerization mechanism
Difference, free radical type and the major class of cationic two can be divided into, both application emphasize particularly on different fields.At this stage, photocuring system draws
Light emitting source is based on high-pressure sodium lamp (wave-length coverage is usually 200-360nm), but high-pressure sodium lamp high energy consumption, and environmental pollution is big, makes
With receiving increasing limitation.The small, energy of LED/light source (wave-length coverage is usually 320-500nm) infringement is high, consumption is low,
It is considered as that can substitute mercury lamp using the favorable substitutes as conventional lighting sources in photocuring system.However, existing most absolutely
Number photocuring system is very poor to the absorbability of LED/light source, tends not to solidify or solidify not exclusively, a small number of applicable systems are then right
The classification limitation of component is more and expensive, mostly foreign patent technical products.In view of this, current technological development is complied with
Trend and practical application request, research and development in 200-500nm wave-length coverages (including mercury lamp and LED/light source) are respectively provided with excellent light and consolidated
The photocuring system for changing performance just seems highly significant.
Summary of the invention
It is an object of the invention to provide a kind of new Photocurable composition.Pass through compositional selecting and optimization, said composition
It is applicable to free radical type, cationic and mixes type photocuring system, there is pole to the light source in 200-500nm wave-length coverages
Good response, curing rate is fast, and developability and pattern integrity are good, and solidification film hardness is high, and the adhesive force on base material is strong.
Specifically, Photocurable composition of the invention, includes following components：
(A) anthracene esters sensitizer, selected from the compound of structure shown in formula (I) and/or using formula (I) compound be main
The macromolecular compound of structure：
R1And R2Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C20Straight or branched alkyl, C3-C20Ring
Alkyl, C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C10Alkenyl；
R3-R10Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C40Straight or branched alkyl, C3-C40Ring
Alkyl, C4-C40Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C40Alkenyl, C6-C40Aryl ,-O-CO-R groups, R generations
Table halogen, C1-C20Straight or branched alkyl, C3-C20Cycloalkyl, C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-
C20Alkenyl, C6-C20Aryl, C2-C40Contain ester group, C2-C40Contain cycloalkyl groups, C3-C20Taken by halogen
The alkyl in generation；Wherein, R3-R10In at least one be-O-CO-R groups；
Also, acyclic-the CH in these groups2- optionally (optionally) by-O- ,-CO- ,-NH- ,-S- or 1,
4- phenylenes are replaced；
(B) response type compound, including at least one compound containing unsaturated double-bond and/or at least one contain epoxy
Compound；
(C) light trigger corresponding with component (B) type.
The Photocurable composition of the present invention has good response to the light in 200-500nm wave-length coverages, is applicable light source
Including but not limited to mercury lamp, halogen lamp, Non-polarized lamp, LED, laser etc..
In view of its excellent performance, Photocurable composition of the invention can be applied in paint, coating, ink and forming material
In terms of material, it is particularly applicable to make：Applied on the base materials such as plastics, metal, glass, ceramics, timber, wall, optical fiber
The coating of cloth；The Protective coatings such as hard coating agent, anti-soil film, antireflection film, damping of shocks film；Photocuring binder, adhesive agent,
Light breakdown type coating, film, article shaped；The optical recording media of hologram material etc.；Optical mold resin, for example, 3D printing
With ink (resin), electronic circuit and semiconductor manufacturing with photoresist, colored filter, black matrix", dry film etc. in display
Electronic material is with photoresist etc.；Interlayer dielectric, light extraction film, brightness enhancement film, encapsulant；Silk-screen printing, offset printing, intaglio plate
The printing inks, inkjet printing light-curable ink such as printing；Eyeglass, lens array, light-guide wave path, light guide plate, light diffusing sheet,
The optical components such as diffraction element；Light separation material, rib wall, nano impression material；Etc..
Detailed description of the invention
The component of the Photocurable composition of the present invention mainly includes component (A)-(C), and this several component belongs to existing skill
Known class compound in art.By using cooperatively for this several component, the Photocurable composition is to 200-500nm wavelength models
Light source (such as mercury lamp and LED) in enclosing has splendid response, and curing rate is fast, and developability and pattern integrity are excellent, solidification
Film hardness is high, and the adhesive force on base material is strong, and cost is relatively low, and application effect is superior.
The Photocurable composition of the present invention mainly includes component (A)-(C), each component will be carried out below more detailed
Explanation.
<Component (A) anthracene esters sensitizer>
As the anthracene esters sensitizer of component (A), selected from the compound of structure shown in formula (I) and/or with formula (I) change
Compound is the macromolecular compound of primary structure：
R1And R2Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C20Straight or branched alkyl, C3-C20Ring
Alkyl, C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C10Alkenyl；
R3-R10Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C40Straight or branched alkyl, C3-C40Ring
Alkyl, C4-C40Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C40Alkenyl, C6-C40Aryl ,-O-CO-R groups, R generations
Table halogen, C1-C20Straight or branched alkyl, C3-C20Cycloalkyl, C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-
C20Alkenyl, C6-C20Aryl, C2-C40Contain ester group, C2-C40Contain cycloalkyl groups, C3-C20Taken by halogen
The alkyl in generation；Wherein, R3-R10In at least one be-O-CO-R groups；
Acyclic-CH in above-mentioned group2- optionally replaced by-O- ,-CO- ,-NH- ,-S- or 1,4- phenylenes.
Herein, acyclic-CH2- refer to-CH that is not in cyclic structure2-, that is, exclude-the CH in cyclic structure2-。
“R3-R10" represent R3、R4、R5、R6、R7、R8、R9And R10。
Preferably, in structure shown in formula (I), R3-R10Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-
C20Straight or branched alkyl, C1-C20Alkoxy or-O-CO-R groups, and R3-R10In at least one be-O-CO-R bases
Group, R represents halogen, C1-C10Straight or branched alkyl, C3-C10Cycloalkyl, C4-C14Alkyl-cycloalkyl or cycloalkyl alkane
Base, C2-C10Alkenyl, C3-C20Contain ester group, C3-C20Contain cycloalkyl groups, C3-C20The alkane being optionally substituted by halogen
Base.
In R optional group, described refers to containing at least one-CO-O- or-O-CO- in group containing ester group,
For example can be containing (methyl) acrylate-based group；Preferably, in addition to ester group, other containing ester group
Structure division belongs to alkyl structure and/or alkenyl structure.It is described to refer to contain at least one in group containing cycloalkyl groups
Individual epoxide group (such as C2-C3Epoxy radicals)；Preferably, in addition to epoxide group, the other structures portion containing cycloalkyl groups
Divide and belong to alkyl structure.
It is further preferred that in structure shown in formula (I), R3-R10Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-
C10Straight or branched alkyl, C1-C10Alkoxy or-O-CO-R groups, and R3-R10In at least one be-O-CO-R bases
Group, R is selected from following groups：
C2-C8Straight or branched alkyl；
C2-C8Alkenyl；
Wherein h=0-3, i=1-4, and as h=0, the hydrogen in cycloalkyl can be optional
Ground is by C1-C4Alkyl is replaced；
-(CH2)j-CO-O-CkH2k+1Or-(CH2)j-O-CO-CkH2k+1, wherein j=1-4, k=1-6；
-(CH2)r- O-CO-CH=CH2, wherein r=1-5；
Wherein m=1-3, n=0-5；
Wherein x=1-3, y=1-2, z=0-3；
Wherein p=1-5, q=0-5；
Cl、F、Br、-(CH2)s(CH2)tCCl、-(CH2)s(CH2)tCF、-(CH2)s(CH2)tCBr, wherein s=1-6, t=
1-6；
And the hydrogen in structure residing for h, j, r, m, x, y, p, s, t is optionally by C1-C4Alkyl is replaced.In these groups,
CkH2k+1、CnH2n+1、CzH2z+1And CqH2q+1Represent the straight or branched alkyl with corresponding carbon number；The value of carbon number includes
Integer value between end value and end value, such as h=0-3 represent that h can be 0,1,2 or 3；These are for those skilled in the art
Speech is very clearly and obvious.
In the compound of structure shown in formula (I), preferably R3-R10In one, two or four be-O-CO-R groups.
When there is two or four-O-CO-R groups, it is preferable that their present positions are symmetrical or center pair in anthracene structure
Claim.
Preferably, in structure shown in formula (I), R1And R2Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-
C10Straight or branched alkyl, C3-C10Cycloalkyl, C4-C10Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C6Alkenyl,
And acyclic-the CH in these groups2- optionally replaced by-O- ,-CO- or 1,4- phenylenes.
It is further preferred that R1And R2Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C4Straight or branched alkane
Base, C3-C6Cycloalkyl, C4-C8Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C6Alkenyl, it is and non-in these groups
Ring-CH2- optionally replaced by-O- or-CO-.
In the present invention, the compound with structure shown in formula (I) can be by commercially available or via existing known method
Easily it is made.For example, prepare can refer to CN104991418A, CN105001081A, CN105037587A,
Method described in JP2013107848A, herein introduces its full text to be used as reference.
As optional anthracene esters sensitizer, it is described can as the macromolecular compound of primary structure using formula (I) compound
Be formula (I) compound pass through polymerize (including homopolymerization and copolymerization), esterification or ester exchange reaction formed by macromolecular compound.
Corresponding synthetic method can refer to interior described in the Chinese patent application of Publication No. CN104991418A, CN105001081A
Hold, herein introduce its full text to be used as reference.
Exemplarily, can be as the anthracene esters sensitizer of component (A) one kind in compound shown in having structure or
Two or more combinations：
In the Photocurable composition of the present invention, as the anthracene esters sensitizer of component (A) can be it is one or two kinds of with
The combination of upper compound, the compound is selected from the compound of structure shown in formula (I) and/or based on formula (I) compound
Want the macromolecular compound of structure.By percentage to the quality, the content of component (A) anthracene esters sensitizer in the composition is
0.001-10%, preferably 0.01-5%, more preferably 0.1-2%.
<Component (B) response type compound>
Response type compound is the key reaction body in photocuring system, generally there is cationoid reaction type compound and freedom
The class of base response type compound two.Component (B) response type compound in the present invention includes at least one chemical combination containing unsaturated double-bond
Thing and/or at least one contain epoxy compounds.Compound can be the chemical shape such as monomer, prepolymer, oligomer, polymer
State.
The compound containing unsaturated double-bond is selected from (methyl) acrylic ester compound and/or alkenyl ethers chemical combination
Thing.
(methyl) acrylic ester compound can be selected from：(methyl) alkyl acrylate, (methyl) dihydroxypropyl
Ester, (methyl) acrylate of (poly-) aklylene glycol, (methyl) acrylate or its dicarboxylic acids of ternary above polyalcohol change
Property thing, epoxy acrylate, polyurethane (methyl) acrylate, polyester acrylate, (methyl) of terminal hydroxyl fluidized polymer
Acrylate, (methyl) acrylate of the oligomeric resin such as urethane resin, silicone resin, spirane resin.
Consider from the using effect such as factor such as curing efficiency, developability, film hardness, base material adhesive force, (methyl) third
Olefin(e) acid ester type compound is preferably (methyl) alkyl acrylate, (methyl) acrylate of (poly-) aklylene glycol, more than ternary
More than one or both of (methyl) acrylate of polyalcohol, epoxy acrylate, polyurethane (methyl) acrylate
Combination.
Without limitation, described (methyl) acrylic ester compound may be selected from one or both of following compounds with
On combination：(methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) isobutyl acrylate, (methyl) acrylic acid uncle
Butyl ester, (methyl) cyclohexyl acrylate, (methyl) ethylhexyl acrylate, (methyl) n-octyl, (methyl) acrylic acid
Different monooctyl ester, bisphenol A epoxy acrylate resin, ethylene glycol two (methyl) acrylate, diethylene glycol two (methyl) acrylate,
Triethylene glycol two (methyl) acrylate, propane diols two (methyl) acrylate, tripropylene glycol two (methyl) acrylate,
1,4- butanediols two (methyl) acrylate, 1,6-HD two (methyl) acrylate, trimethylolethane trimethacrylate (methyl) third
Olefin(e) acid ester, trimethylolpropane tris (methyl) acrylate, pentaerythrite three (methyl) acrylate, pentaerythrite four (methyl)
Acrylate, dipentaerythritol five (methyl) acrylate, dipentaerythritol six (methyl) acrylate etc..
The alkenyl ether compound may be selected from vinyl ethers, 1- acrylic ethers, 1- cyclobutenyls ethers, 1- amylenes
Pyridyl ethers compound, optimal ethylene pyridyl ethers compound.It is highly preferred that vinyl ethers compound may be selected from Triethylene glycol divinyl
Base ether, 1,4- cyclohexane dimethanols divinyl ether, 4- hydroxy butyl vinyl ethers, glycerol carbonate vinyl ethers, dodecyl
Combination more than one or both of vinyl ethers etc..
Described is selected from glycidyl ether type epoxy resin, glycidyl ester epoxy resin, contracting containing epoxy compounds
Water glycerine amine epoxy resin, linear aliphatic same clan epoxy resin, aliphatic category epoxy resin and oxygen heterocycle butane.
The effect such as factor such as curing efficiency, developability, film hardness, base material adhesive force used from compatibility considers, above-mentioned to contain
Glycidyl ether type epoxy resin, the fat such as the preferred bisphenol A type epoxy resin of epoxy compounds, aliphatic glycidyl ether resin
Fat same clan epoxy resin and oxygen heterocycle butane.
Exemplary type, it is described containing epoxy compounds can be glycerin triglycidyl ether, ethylene glycol and shrink sweet
Oily ether, 3,4- epoxycyclohexyl-methyl -3,4- epoxycyclohexyls formic acid esters, ethanedioic acid double (3,4- epoxycyclohexanecarboxylates), three
Hydroxymethyl-propane glycidol ether, 1,2- epoxy -4- vinyl cyclohexanes, 2,2'- [(1- methyl ethylidene) double (4,1- Asias benzene
Base formaldehyde)] homopolymer (bisphenol A type epoxy resin) of bisoxirane, 3- Oxyranyle 7- oxabicyclos [4,1,0] heptan
Alkane, ethylene glycol bisglycidyl ether, C12-C14Alkyl glycidyl ether, 3- methyl -3- ethene hydroxymethyl-oxetane, 3- first
Double (3- ethyl -3- oxetanylmethoxies) butane of many ethoxylated methyl oxetanes of base -3- ethene hydroxyls, 1,4-,
1,6- double (3- ethyl -3- oxetanylmethoxies) hexane, pentaerythrites three (3- ethyl -3- oxetanylmethyls)
Ether, 3- methyl -3- hydroxymethyl oxetanes, 3- ethyl -3- hydroxymethyl oxetanes, 3- ethyls -3- (2- ethyl hexyls
Epoxide methyl) oxetanes, double [(3- ethyl -3- oxetanylmethoxies) methyl] propane of 1,3-, polyethylene glycol are double
(3- ethyl -3- oxetanylmethyls) ether, isobutoxymethyl (3- ethyl -3- oxetanylmethyls) ether, second two
Alcohol double (3- ethyl -3- oxetanylmethyls) ether, tristane diyl dimethylene (3- ethyl -3- oxetanyls
Methyl) ether, trimethylolpropane tris (3- ethyl -3- oxetanylmethyls) ether, (3- ethyl -3- the oxa-s of pentaerythrite four
Cyclobutane ylmethyl) more than one or both of ether etc. combination.
It is described to be also selected from containing epoxy compounds or including the change with following structure in addition to mentioned kind
Compound：
Above-mentioned (methyl) acrylic ester compound belongs to radical reaction type compound, belongs to sun containing epoxy compounds
Ionic reaction type compound, the characteristics of alkenyl ether compound then has two types simultaneously.Examined from the angle of performance priority
Consider, as response type compound, (methyl) acrylic ester compound is adapted to free radical type photocuring system, chemical combination containing epoxy radicals
Thing is adapted to cationic photocuring system, and then both of which is applicable alkenyl ether compound.
The present invention can flexibly select the composition of component (B) according to required photocuring system type.For radical UV curing
System, component (B) can be (methyl) acrylic ester compound and/or alkenyl ether compound；It is solid for cationic photopolymerization
Change system, component (B) can contain epoxy compounds and/or alkenyl ether compound；For mixing type photocuring system,
Component (B) can be (methyl) acrylic ester compound, containing epoxy compounds and optionally alkenyl ether compound
Combination.
In the Photocurable composition of the present invention, by percentage to the quality, the content of component (B) is 10-90%, preferably
40-90%.
<Component (C) light trigger corresponding with component (B) type>
In photocuring system, the classification correspondence of cation/radical reaction type compound and light trigger is very high, sun from
Sub- response type compound generally requires cationic photoinitiator to trigger polymerization, and radical reaction type compound then needs freedom
Fundamental mode light trigger, the effect that could have so obtained.
For cation photocuring system, i.e., when component (B) is selected from cationoid reaction type compound, component of the invention
(C) be cationic photoinitiator, and be one or both of aryl diazonium salts, salt compounded of iodine, sulfosalt, the luxuriant molysite of aryl with
On combination.
Based on considering for the composite factors such as cost, for example light-initiated efficiency of the effect used cooperatively, curing rate, component (C)
It is preferred that salt compounded of iodine and/or sulfosalt photoinitiator, the change particularly preferably with the structure as shown in following formula (II) and/or (III)
Compound：
Wherein, R11And R12Hydrogen, C are represented independently of one another1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl
Or acyclic-the CH in alkyl-cycloalkyl, and these groups2- optionally replaced by-O- ,-S- or 1,4- phenylenes；
R13And R14Hydrogen, C are represented independently of one another1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl or alkyl
Cycloalkyl, C6-C20Aryl, and the acyclic-CH in these groups2- optionally taken by-O- ,-S- or 1,4- phenylenes
Generation；
R15Represent C6-C20Aryl, C1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl or alkyl-cycloalk
Acyclic-CH in base, substitution or unsubstituted Phenylsulfanylphenyl, and these groups2- optionally by-O- ,-S- or 1,4-
Phenylene is replaced；
X-PF is represented independently of one another6 -、SbF6 -、CF3SO3 -、C4F9SO3 -、C8F17SO3 -、(SO2C4F9)2N-Or B (C6M5)4 -
(M represents H, F, Cl, Br).
As preferred structure, in the compound of structure shown in formula (II) and (III)：
R11And R12Hydrogen, C are represented independently of one another1-C12Straight or branched alkyl, C4-C10Cycloalkyl-alkyl or alkyl
Acyclic-CH in cycloalkyl, and these groups2- optionally replaced by-O-；
R13And R14Hydrogen, C are represented independently of one another1-C10Straight or branched alkyl, C4-C10Cycloalkyl-alkyl or alkyl
Cycloalkyl, C6-C12Aryl, and the acyclic-CH in these groups2- optionally taken by-O- ,-S- or 1,4- phenylenes
Generation；
R15Represent C6-C10Aryl, the acyclic-CH in substitution or unsubstituted Phenylsulfanylphenyl, and these groups2-
Optionally replaced by-O- ,-S- or 1,4- phenylenes.
It is further preferred that above-mentioned salt compounded of iodine and sulfosalt photoinitiator can include following structure：
For radical UV curing system, i.e., when component (B) is selected from radical reaction type compound, component of the invention
(C) it is radical photoinitiator.
Common radical photoinitiator has Dialkoxy acetophenones class, alpha-hydroxyalkyl benzophenone class, α-amine alkyl phenones
Class, acylphosphine oxide, benzophenone, benzoin class, benzil class, heterocycle arone class, oxime ester lightlike initiating agent etc..
Based on considering for the composite factors such as cost, for example light-initiated efficiency of the effect used cooperatively, curing rate, in the present invention
Benzophenone, alpha-hydroxyalkyl benzophenone class and/or α-amine alkyl phenones are selected from as the radical photoinitiator of component (C)
Class, benzil class compound.
Exemplarily, be as the radical photoinitiator of component (C) one kind in compound shown in having structure or
Two or more combinations：
It is easily understood that for Free radical-Cationic Hybrid photocuring system, i.e., when simultaneously component (B) contains certainly
By base response type and cationoid reaction type compound when, component (C) of the invention by above-mentioned radical photoinitiator and sun from
Subtype light trigger is constituted.But there is also special circumstances --- in type Photocurable composition is mixed, contain salt compounded of iodine and/or sulphur
Cationoid reaction type compound crosslink solidification of the component (C) of salt type cationic light trigger in component (B) is triggered
During can discharge free radical simultaneously, and then further trigger the radical reaction type compound in component (B).Namely
Say, when component (C) includes salt compounded of iodine and/or sulfosalt photoinitiator, it is playing cationic photoinitiator effect
Simultaneously, it may have the partial function of free radical type.Now, radical photoinitiator and optional component.
In the Photocurable composition of the present invention, by percentage to the quality, the content of component (C) in the composition is
0.001-20%, preferably 0.1-10%.
<Component (D) other components>
In addition to said components (A)-(C), according to products application needs, Photocurable composition of the invention is also alternative
Ground adds organic and/or inorganic assistant commonly used in the art, including but not limited to pigment, levelling agent, dispersant, curing agent,
Surfactant, solvent etc., this will be apparent to those skilled in the art.In addition, not imitated to composition application
On the premise of fruit has a negative impact, other sensitizers and/or light trigger can be also added in composition with compounding use.
One or more macromoleculars or high-molecular compound are also optionally added in needs, said composition according to applying
To improve the application performance of composition in use, this macromolecular or high-molecular compound can be polyalcohol or polyester
Polyalcohol；Also the polymer for not containing reactive functionality is optionally added, these polymer are typically to contain phenolic hydroxyl group, carboxylic
The resin of the acidic functionalities such as base.
<The preparation of Photocurable composition>
The Photocurable composition of the present invention can be obtained by being well mixed after each component is weighed according to quantity.
The commercially available prod of curing field particularly mid- to high-end product is based on import at this stage, and these products possess mostly
Patented technology, product price is high, and domestic enterprise lacks core technology and independent intellectual property right, under tight technology barriers,
Enterprise development or even research and development layout all receive very big limitation.The present invention passes through constituent optimization, the sense of gained Photocurable composition
Optical wavelength range is big, and photocuring effect is good, is applied, has in many-sides such as paint, coating, ink, moulding materials
Stronger technology and the market competitiveness.
Embodiment
The present invention is described in further detail below with reference to specific embodiment, but be should not be construed as to the present invention
The limitation of protection domain.
Unless otherwise instructed, number described below is parts by weight.The reference implication respectively abridged is as follows：
A1：
A2：
A3：
A4：
B1：Dimethacrylate；
B2：Bisphenol A epoxy acrylate resin (SM6105-80)；
B3：Dodecyl vinyl；
B4：Ethylene glycol and glycidol ether；
B5：
C1：
C2：
C3:
C4：
1st, Photocurable composition is prepared
Formula prepares Photocurable composition shown according to the form below 1.
Table 1
2nd, performance test
(1) film forming is tested under high-pressure sodium lamp
Photocurable composition is stirred under yellow fluorescent lamp, feeding dries 5min in roller coating film forming in PET templates at 90 DEG C
Solvent is removed, the film of about 2 μm of thickness is formed.The substrate for being formed with film is cooled to room temperature, mask plate is enclosed, uses high-pressure mercury
Lamp (exposure machine model RW-UV70201, light intensity 50mW/cm2) irradiation film is exposed, time for exposure 30s.Visually observe
To evaluate the film forming situation of exposure area.
Develop with 30s is impregnated in the 1% NaOH aqueous solution at a temperature of 25 DEG C, then with milli-Q water, air-dry；Connect
Baking 30min after in 240 DEG C of baking oven, obtains the pattern of mask plate transfer.Base is observed with SEM (SEM)
Pattern on plate, to evaluate developability and pattern integrity.
Film forming situation evaluation criterion is as follows：
○：Film surface is smooth；
◎：There is flaw on film surface；
●：Can not film forming.
Developability evaluation criterion is as follows:
○：Residue is not observed in unexposed portion；
◎：In unexposed portion it was observed that a small amount of residue, but residual quantity can receive；
●：In unexposed portion it was observed that obvious residue.
Pattern integrity evaluation criterion is as follows:
○：Pattern defect is not observed；
◎：It was observed that fraction pattern has fewer defects；
●：Substantially it was observed that many pattern defects.
Evaluation result is as shown in table 2.
Table 2
(2) film forming is tested under LED/light source
Photocurable composition is stirred under yellow fluorescent lamp, feeding dries 5min in roller coating film forming in PET templates at 90 DEG C
Solvent is removed, the film of about 2 μm of thickness is formed.The substrate for being formed with film is cooled to room temperature, mask plate is enclosed, using wavelength
395nm, light intensity 1500mW/cm2LED/light source, the substrate of film will be formed with and be maintained at 10cm with fluorescent tube distance, be exposed
And detect its primary solidification time.
The primary solidification time refers to that in the case where LED/light source irradiates material surface hardness is reached with the Chinese board advanced drawing lead of 1H
Pen portrays the time for occurring without vestige, and the primary solidification time can be used to weigh the efficiency of initiation of light trigger.
After primary solidification, with identical in above-mentioned (1) develop and rear baking procedure, and evaluate using identical standard
Its developability and pattern integrity.
Test result is as shown in table 3 below.
Table 3
(3) base material adhesive force is tested
Using the Photocurable composition of embodiment 1 as representative, reference《The cut of GBT9286-1998 paint and varnish paint films is real
Test》, the skill in using a kitchen knife in cookery is drawn using hundred lattice, using QFH paint film lattice drawing instrument, adhesive force of the Photocurable composition on different substrate materials is surveyed
Examination.
Specific method is as follows：
Photocurable composition is uniformly applied on different base materials, solidification (is applied under high-pressure sodium lamp and LED lamp source respectively
Smear and condition of cure is as described above described in (1) and (2), without using mask plate, expose and exposed under 30s, LED/light source under high-pressure sodium lamp
3s), room temperature places 24h and carries out aging after the completion of solidification, then using cross-cut tester laterally and longitudinally each stroke of 1 knife to form 100
Tiny grid, then with each brush of hairbrush diagonal five times, is attached on otch with 3M600 adhesive tapes and pulled open again, use magnifying glass
The situation of grid area is observed, film is evaluated to base material degree of adhesion by evaluating the integrated degree of film in grid.Grid
Interior film is more complete, represents that adhesive ability is stronger.
Evaluation criterion is as follows：
A：The edge of otch is completely smooth, and grid edge does not have any peeling；
B：There is actual spoilage≤5% in small pieces peeling, Hua Ge areas in the intersection of otch；
C：There is peeling at the edge and/or intersection of otch, and its area 5%-30% (is free of 5%)；
D：There is part to peel off or whole large stretch of peeling or all peelings along notching edge, or partial grid is peeled off by full wafer.Stripping
The area fallen is more than 30%.
Evaluation result is as shown in table 4 below.
Table 4
With reference to table 2-4 test result can be seen that the present invention Photocurable composition all have under mercury lamp and LED/light source
There is good photocuring effect, sensitivity is high, and curing rate is fast, and developability and pattern integrity are good, and hardness of film is high, not
With showing very strong adhesive force on base material.
Claims (24)
1. a kind of new Photocurable composition, includes following components：
(A) anthracene esters sensitizer, selected from the compound of structure shown in formula (I) and/or using formula (I) compound as primary structure
Macromolecular compound：
R1And R2Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C20Straight or branched alkyl, C3-C20Cycloalkyl,
C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C10Alkenyl；
R3-R10Hydrogen, nitro, cyano group, halogen, C are represented independently of one another1-C40Straight or branched alkyl, C3-C40Cycloalkyl,
C4-C40Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C40Alkenyl, C6-C40Aryl ,-O-CO-R groups, R represents halogen
Element, C1-C20Straight or branched alkyl, C3-C20Cycloalkyl, C4-C20Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C20's
Alkenyl, C6-C20Aryl, C2-C40Contain ester group, C2-C40Contain cycloalkyl groups, C3-C20Be optionally substituted by halogen
Alkyl；Wherein, R3-R10In at least one be-O-CO-R groups；
Also, acyclic-the CH in these groups2- optionally replaced by-O- ,-CO- ,-NH- ,-S- or 1,4- phenylenes；
(B) response type compound, including at least one compound containing unsaturated double-bond and/or at least one chemical combination containing epoxy radicals
Thing；
(C) light trigger corresponding with component (B) type.
2. Photocurable composition according to claim 1, it is characterised in that：In structure shown in formula (I), R3-R10Each solely
On the spot represent hydrogen, nitro, cyano group, halogen, C1-C20Straight or branched alkyl, C1-C20Alkoxy or-O-CO-R groups,
And R3-R10In at least one be-O-CO-R groups, R represents halogen, C1-C10Straight or branched alkyl, C3-C10Cycloalkanes
Base, C4-C14Alkyl-cycloalkyl or cycloalkyl-alkyl, C2-C10Alkenyl, C3-C20Contain ester group, C3-C20Contain ring
Epoxide group, C3-C20The alkyl being optionally substituted by halogen.
3. Photocurable composition according to claim 1 or 2, it is characterised in that：In structure shown in formula (I), R3-R10Each
Independently represent hydrogen, nitro, cyano group, halogen, C1-C10Straight or branched alkyl, C1-C10Alkoxy or-O-CO-R bases
Group, and R3-R10In at least one be-O-CO-R groups, R is selected from following groups：
C2-C8Straight or branched alkyl；
C2-C8Alkenyl；
Wherein h=0-3, i=1-4, and as h=0, hydrogen in cycloalkyl optionally by
C1-C4Alkyl is replaced；
-(CH2)j-CO-O-CkH2k+1Or-(CH2)j-O-CO-CkH2k+1, wherein j=1-4, k=1-6；
-(CH2)r- O-CO-CH=CH2, wherein r=1-5；
Wherein m=1-3, n=0-5；
Wherein x=1-3, y=1-2, z=0-3；
Wherein p=1-5, q=0-5；
Cl、F、Br、-(CH2)s(CH2)tCCl、-(CH2)s(CH2)tCF、-(CH2)s(CH2)tCBr, wherein s=1-6, t=1-6；
And the hydrogen in structure residing for h, j, r, m, x, y, p, s, t is optionally by C1-C4Alkyl is replaced.
4. Photocurable composition according to claim 1, it is characterised in that：R3-R10In one, two or four be-
O-CO-R groups.
5. the Photocurable composition according to claim 1 or 4, it is characterised in that：When there is two or four-O-CO-R bases
During group, their present positions are symmetrical or centrosymmetric in anthracene structure.
6. Photocurable composition according to claim 1, it is characterised in that：In structure shown in formula (I), R1And R2Each solely
On the spot represent hydrogen, nitro, cyano group, halogen, C1-C10Straight or branched alkyl, C3-C10Cycloalkyl, C4-C10Alkyl-cycloalk
Base or cycloalkyl-alkyl, C2-C6Alkenyl, and the acyclic-CH in these groups2- optionally sub- by-O- ,-CO- or 1,4-
Phenyl is replaced.
7. the Photocurable composition according to claim 1 or 6, it is characterised in that：R1And R2Hydrogen, nitre are represented independently of one another
Base, cyano group, halogen, C1-C4Straight or branched alkyl, C3-C6Cycloalkyl, C4-C8Alkyl-cycloalkyl or cycloalkyl-alkyl,
C2-C6Alkenyl, and the acyclic-CH in these groups2- optionally replaced by-O- or-CO-.
8. Photocurable composition according to claim 1, it is characterised in that：The compound containing unsaturated double-bond is selected from
(methyl) acrylic ester compound and/or alkenyl ether compound.
9. Photocurable composition according to claim 8, it is characterised in that：(methyl) the acrylic ester compound choosing
From more than (methyl) alkyl acrylate, (methyl) crylic acid hydroxy ester, (methyl) acrylate of (poly-) aklylene glycol, ternary
(methyl) acrylate of polyalcohol or secondly carboxyl acid modified thing, epoxy acrylate, polyurethane (methyl) acrylate, polyester
Acrylate, (methyl) acrylate of terminal hydroxyl fluidized polymer, (methyl) acrylate of oligomeric resin.
10. Photocurable composition according to claim 8 or claim 9, it is characterised in that：(methyl) the esters of acrylic acid chemical combination
Thing is (methyl) alkyl acrylate, (poly-) aklylene glycol (methyl) acrylate, (methyl) third of ternary above polyalcohol
Combination more than one or both of olefin(e) acid ester, epoxy acrylate, polyurethane (methyl) acrylate.
11. Photocurable composition according to claim 8, it is characterised in that：The alkenyl ether compound is selected from second
Alkenyl ethers, 1- acrylic ethers, 1- cyclobutenyls ethers, 1- amylene pyridyl ethers compounds, optimal ethylene pyridyl ethers compound.
12. Photocurable composition according to claim 11, it is characterised in that：The vinyl ethers compound is selected from three
Ethylene glycol divinyl ether, 1,4- cyclohexane dimethanols divinyl ether, 4- hydroxy butyl vinyl ethers, glycerol carbonate vinyl
Combination more than one or both of ether, dodecyl vinyl.
13. Photocurable composition according to claim 1, it is characterised in that：Described is selected from contracting containing epoxy compounds
Water glycerine ether type epoxy resins, glycidyl ester epoxy resin, glycidyl amine epoxy resin, linear aliphatic same clan epoxy
Resin, aliphatic category epoxy resin and oxygen heterocycle butane.
14. the Photocurable composition according to claim 1 or 13, it is characterised in that：Described selects containing epoxy compounds
From glycidol ether based epoxy resin, aliphatic category epoxy resin and oxygen heterocycle butane.
15. Photocurable composition according to claim 1, it is characterised in that it is described be selected from containing epoxy compounds or
Including the compound with following structure：
16. Photocurable composition according to claim 1, it is characterised in that：For radical UV curing system, component
(B) by (methyl) acrylic ester compound and/or alkenyl ethers compound group into；For cation photocuring system, group
Point (B) by containing epoxy compounds and/or alkenyl ethers compound group into；For Free radical-Cationic Hybrid photocuring
System, component (B) is by (methyl) acrylic ester compound, containing epoxy compounds and optionally alkenyl ether compound
Composition.
17. the Photocurable composition according to claim 1 or 16, it is characterised in that：For cation photocuring system, group
It is cationic photoinitiator to divide (C), and is one or both of aryl diazonium salts, salt compounded of iodine, sulfosalt, the luxuriant molysite of aryl
Combination above.
18. Photocurable composition according to claim 17, it is characterised in that：Component (C) is selected from salt compounded of iodine and/or sulphur
Salt photoinitiator.
19. Photocurable composition according to claim 18, it is characterised in that component (C), which is selected from, has such as following formula (II)
And/or the compound of structure shown in (III)：
Wherein, R11And R12Hydrogen, C are represented independently of one another1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl or alkyl
Acyclic-CH in cycloalkyl, and these groups2- optionally replaced by-O- ,-S- or 1,4- phenylenes；
R13And R14Hydrogen, C are represented independently of one another1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl or alkyl-cycloalk
Base, C6-C20Aryl, and the acyclic-CH in these groups2- optionally replaced by-O- ,-S- or 1,4- phenylenes；
R15Represent C6-C20Aryl, C1-C20Straight or branched alkyl, C4-C20Cycloalkyl-alkyl or alkyl-cycloalkyl, take
Acyclic-CH in generation or unsubstituted Phenylsulfanylphenyl, and these groups2- optionally by-O- ,-S- or 1,4- phenylenes
Replaced；
X-PF is represented independently of one another6 -、SbF6 -、CF3SO3 -、C4F9SO3 -、C8F17SO3 -、(SO2C4F9)2N-Or B (C6M5)4 -(M generations
Table H, F, Cl, Br).
20. the Photocurable composition according to claim 1 or 16, it is characterised in that：For radical UV curing system, group
It is radical photoinitiator to divide (C), even selected from benzophenone, alpha-hydroxyalkyl benzophenone class and/or α-amine alkylbenzene ketone, benzene
Acyl class compound.
21. the Photocurable composition according to claim 1 or 16, it is characterised in that：For Free radical-Cationic Hybrid
Photocuring system, component (C) is made up of radical photoinitiator and cationic photoinitiator, wherein, cationic light draws
Hair agent is combinations more than one or both of aryl diazonium salts, salt compounded of iodine, sulfosalt, the luxuriant molysite of aryl, free radical type light
Initiator is selected from benzophenone, alpha-hydroxyalkyl benzophenone class and/or α-amine alkylbenzene ketone compounds.
22. the Photocurable composition according to claim 1 or 16, it is characterised in that：For Free radical-Cationic Hybrid
Photocuring system, component (C) includes salt compounded of iodine and/or sulfosalt photoinitiator.
23. application of the Photocurable composition any one of claim 1-22 in curing field.
24. application according to claim 23, it is characterised in that：The curing field include paint, coating, ink and
Moulding material.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610235085.0A CN107300830B (en) | 2016-04-15 | 2016-04-15 | Novel photocuring composition and application thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610235085.0A CN107300830B (en) | 2016-04-15 | 2016-04-15 | Novel photocuring composition and application thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN107300830A true CN107300830A (en) | 2017-10-27 |
| CN107300830B CN107300830B (en) | 2021-03-30 |
Family
ID=60136808
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201610235085.0A Active CN107300830B (en) | 2016-04-15 | 2016-04-15 | Novel photocuring composition and application thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN107300830B (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108319109A (en) * | 2017-01-17 | 2018-07-24 | 常州强力电子新材料股份有限公司 | A kind of application of photosensitive polymer combination in manufacturing printed wiring board |
| CN108319111A (en) * | 2017-01-17 | 2018-07-24 | 常州强力电子新材料股份有限公司 | A kind of photosensitive polymer combination for liquid crystal display |
| CN108329657A (en) * | 2018-03-09 | 2018-07-27 | 北京瑞达科博技术有限公司 | Free radical-Cationic Hybrid curing glass fiber reinforcement plastic feed composition |
| WO2019019924A1 (en) * | 2017-07-27 | 2019-01-31 | 常州强力先端电子材料有限公司 | Oxetane monomer compound and preparation method therefor |
| CN110317482A (en) * | 2018-03-28 | 2019-10-11 | 常州格林感光新材料有限公司 | The method handled for the Photocurable composition of anti-corrosion of metal, its application and corrosion protection of metal surface |
| CN110819161A (en) * | 2019-11-18 | 2020-02-21 | 南京森工生物科技有限公司 | Printable developing ink and preparation method thereof |
| CN112126274A (en) * | 2020-09-16 | 2020-12-25 | 四川乐凯新材料有限公司 | Photocurable composition for PCB containing alkenyl ether and/or oxetane compound |
Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1782878A (en) * | 2004-11-26 | 2006-06-07 | 东丽株式会社 | Positive type photo-sensitive siloxane composition, cured film formed from the composition and device incorporating the cured film |
| CN1882304A (en) * | 2003-11-21 | 2006-12-20 | 密苏里大学管理者 | Photoinitiator systems with anthracene-based electron donors for curing cationically polymerizable resins |
| CN101069129A (en) * | 2004-12-03 | 2007-11-07 | 巴斯福股份公司 | Radiation-curable coating substances |
| CN102702431A (en) * | 2012-05-30 | 2012-10-03 | 深圳市惠乐光电有限公司 | Cyclohexyl copolymer resin and preparation method thereof as well as color photoresist and preparation method thereof |
| CN104423166A (en) * | 2013-08-23 | 2015-03-18 | 财团法人工业技术研究院 | Photosensitive Composition And Photoresist |
| CN105001081A (en) * | 2015-06-24 | 2015-10-28 | 常州强力电子新材料股份有限公司 | Anthracene-series sensitizer and application of same in UV-LED light-curing system |
| CN105037587A (en) * | 2015-06-24 | 2015-11-11 | 常州强力先端电子材料有限公司 | Sensitizer applicable to UV-LED photocuring system |
-
2016
- 2016-04-15 CN CN201610235085.0A patent/CN107300830B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1882304A (en) * | 2003-11-21 | 2006-12-20 | 密苏里大学管理者 | Photoinitiator systems with anthracene-based electron donors for curing cationically polymerizable resins |
| CN1782878A (en) * | 2004-11-26 | 2006-06-07 | 东丽株式会社 | Positive type photo-sensitive siloxane composition, cured film formed from the composition and device incorporating the cured film |
| CN101069129A (en) * | 2004-12-03 | 2007-11-07 | 巴斯福股份公司 | Radiation-curable coating substances |
| CN102702431A (en) * | 2012-05-30 | 2012-10-03 | 深圳市惠乐光电有限公司 | Cyclohexyl copolymer resin and preparation method thereof as well as color photoresist and preparation method thereof |
| CN104423166A (en) * | 2013-08-23 | 2015-03-18 | 财团法人工业技术研究院 | Photosensitive Composition And Photoresist |
| CN105001081A (en) * | 2015-06-24 | 2015-10-28 | 常州强力电子新材料股份有限公司 | Anthracene-series sensitizer and application of same in UV-LED light-curing system |
| CN105037587A (en) * | 2015-06-24 | 2015-11-11 | 常州强力先端电子材料有限公司 | Sensitizer applicable to UV-LED photocuring system |
Non-Patent Citations (1)
| Title |
|---|
| 陈明等: "混杂光固化体系的原理及应用", 《感光科学与光化学》 * |
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108319109A (en) * | 2017-01-17 | 2018-07-24 | 常州强力电子新材料股份有限公司 | A kind of application of photosensitive polymer combination in manufacturing printed wiring board |
| CN108319111A (en) * | 2017-01-17 | 2018-07-24 | 常州强力电子新材料股份有限公司 | A kind of photosensitive polymer combination for liquid crystal display |
| CN108319109B (en) * | 2017-01-17 | 2021-08-03 | 常州强力电子新材料股份有限公司 | Application of photosensitive resin composition in manufacturing printed circuit board |
| CN108319111B (en) * | 2017-01-17 | 2021-09-07 | 常州强力电子新材料股份有限公司 | Photosensitive resin composition for liquid crystal display |
| WO2019019924A1 (en) * | 2017-07-27 | 2019-01-31 | 常州强力先端电子材料有限公司 | Oxetane monomer compound and preparation method therefor |
| CN108329657A (en) * | 2018-03-09 | 2018-07-27 | 北京瑞达科博技术有限公司 | Free radical-Cationic Hybrid curing glass fiber reinforcement plastic feed composition |
| CN110317482A (en) * | 2018-03-28 | 2019-10-11 | 常州格林感光新材料有限公司 | The method handled for the Photocurable composition of anti-corrosion of metal, its application and corrosion protection of metal surface |
| CN110819161A (en) * | 2019-11-18 | 2020-02-21 | 南京森工生物科技有限公司 | Printable developing ink and preparation method thereof |
| CN112126274A (en) * | 2020-09-16 | 2020-12-25 | 四川乐凯新材料有限公司 | Photocurable composition for PCB containing alkenyl ether and/or oxetane compound |
Also Published As
| Publication number | Publication date |
|---|---|
| CN107300830B (en) | 2021-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN107325237A (en) | A kind of Free radical-Cationic Hybrid photocuring system and its application | |
| CN107300830A (en) | A kind of new Photocurable composition and its application | |
| CN107300832A (en) | A kind of Photocurable composition and its application | |
| CN107300831A (en) | A kind of curable compositions solidified applied to LED light | |
| KR910003981B1 (en) | Solder resist ink composition | |
| CN107300829A (en) | A kind of application of novel cation photocuring system and combinations thereof | |
| CN102858738B (en) | Liquid radiation curable resins for additive fabrication comprising a triaryl sulfonium borate cationic photoinitiator | |
| CN107300833A (en) | A kind of application of new free-radical photocuring system and combinations thereof | |
| CN108314911A (en) | A kind of UVLED curable wood coatings | |
| CN102272227A (en) | Radiation curable resin composition and rapid three-dimensional imaging process using the same | |
| TW201808874A (en) | Flourene multifunctional photoinitiator, method of production, and the use thereof, and photopolymer comprising the same and the use thereof | |
| CN104428712B (en) | Photocurable resin composition, its solidfied material and printed circuit board (PCB) | |
| JP2015129074A (en) | Composition for reinforcing glass end face, glass plate material, and method of producing glass plate material | |
| JPWO2018084121A1 (en) | Curable insulating composition for printed wiring board, dry film, cured product, printed wiring board, and method for producing curable insulating composition for printed wiring board | |
| CN104854155B (en) | Photocurable composition | |
| CN108951281A (en) | A kind of cured paper film coating of UV-LED/EB | |
| CN1205784A (en) | Photosensitive resin compsn. | |
| JP2014186266A (en) | Resin composition for solder resist and printed wiring board | |
| CN111324009A (en) | Photocurable composition and use thereof | |
| TW201910447A (en) | Monomer mixture and hardenable composition comprising the same | |
| JPH07212012A (en) | Manufacture of photopolymeric mixture and solder resist mask | |
| CN108319111B (en) | Photosensitive resin composition for liquid crystal display | |
| JP7556786B2 (en) | Radiation-curable compositions containing modified pigments and their applications | |
| CN108319109B (en) | Application of photosensitive resin composition in manufacturing printed circuit board | |
| DE2713797C3 (en) | Photopolymerizable coating agents |
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 | ||
| TR01 | Transfer of patent right |
Effective date of registration: 20240311 Address after: 213159 Wucheng Industrial Park, Zhenglu Town, Tianning District, Changzhou City, Jiangsu Province Patentee after: CHANGZHOU TRONLY ADVANCED ELECTRONIC MATERIALS Co.,Ltd. Country or region after: China Patentee after: Changzhou Tronly New Electronic Materials Co.,Ltd. Patentee after: Changzhou Qiangli photoelectric material Co.,Ltd. Address before: 213011 Qian Jia Industrial Park, Guan yuan town, Wujin District, Jiangsu, Changzhou Patentee before: Changzhou Tronly New Electronic Materials Co.,Ltd. Country or region before: China Patentee before: CHANGZHOU TRONLY ADVANCED ELECTRONIC MATERIALS Co.,Ltd. |
|
| TR01 | Transfer of patent right |