TW201630878A - 硼酸鋶鹽、酸產生劑、硬化性組成物及硬化體 - Google Patents
硼酸鋶鹽、酸產生劑、硬化性組成物及硬化體 Download PDFInfo
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- TW201630878A TW201630878A TW105101006A TW105101006A TW201630878A TW 201630878 A TW201630878 A TW 201630878A TW 105101006 A TW105101006 A TW 105101006A TW 105101006 A TW105101006 A TW 105101006A TW 201630878 A TW201630878 A TW 201630878A
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- acid generator
- weight
- borate salt
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- 125000002704 decyl 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])* 0.000 description 1
- 230000002542 deteriorative effect Effects 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical compound C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
- LTYMSROWYAPPGB-UHFFFAOYSA-N diphenyl sulfide Chemical compound C=1C=CC=CC=1SC1=CC=CC=C1 LTYMSROWYAPPGB-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- SFSPUVKCNQHXPP-UHFFFAOYSA-N disodium dioxido-(2,3,4,5,6-pentafluorophenoxy)borane Chemical compound [Na+].B(OC1=C(C(=C(C(=C1F)F)F)F)F)([O-])[O-].[Na+] SFSPUVKCNQHXPP-UHFFFAOYSA-N 0.000 description 1
- ODQWQRRAPPTVAG-GZTJUZNOSA-N doxepin Chemical compound C1OC2=CC=CC=C2C(=C/CCN(C)C)/C2=CC=CC=C21 ODQWQRRAPPTVAG-GZTJUZNOSA-N 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- NHOGGUYTANYCGQ-UHFFFAOYSA-N ethenoxybenzene Chemical compound C=COC1=CC=CC=C1 NHOGGUYTANYCGQ-UHFFFAOYSA-N 0.000 description 1
- 125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 description 1
- UHKJHMOIRYZSTH-UHFFFAOYSA-N ethyl 2-ethoxypropanoate Chemical compound CCOC(C)C(=O)OCC UHKJHMOIRYZSTH-UHFFFAOYSA-N 0.000 description 1
- GFUIDHWFLMPAGY-UHFFFAOYSA-N ethyl 2-hydroxy-2-methylpropanoate Chemical compound CCOC(=O)C(C)(C)O GFUIDHWFLMPAGY-UHFFFAOYSA-N 0.000 description 1
- YOQPJXKVVLAWRU-UHFFFAOYSA-N ethyl carbamate;methyl prop-2-enoate Chemical compound CCOC(N)=O.COC(=O)C=C YOQPJXKVVLAWRU-UHFFFAOYSA-N 0.000 description 1
- 229940116333 ethyl lactate Drugs 0.000 description 1
- 229940117360 ethyl pyruvate Drugs 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- RMBPEFMHABBEKP-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2C3=C[CH]C=CC3=CC2=C1 RMBPEFMHABBEKP-UHFFFAOYSA-N 0.000 description 1
- 238000007429 general method Methods 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052735 hafnium Inorganic materials 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- CAYGQBVSOZLICD-UHFFFAOYSA-N hexabromobenzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1Br CAYGQBVSOZLICD-UHFFFAOYSA-N 0.000 description 1
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000001939 inductive effect Effects 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012796 inorganic flame retardant Substances 0.000 description 1
- 239000001023 inorganic pigment Substances 0.000 description 1
- 239000011229 interlayer Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 230000001678 irradiating effect Effects 0.000 description 1
- 125000004491 isohexyl group Chemical group C(CCC(C)C)* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-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
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 1
- 229910052753 mercury Inorganic materials 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 238000005649 metathesis reaction Methods 0.000 description 1
- BDJSOPWXYLFTNW-UHFFFAOYSA-N methyl 3-methoxypropanoate Chemical compound COCCC(=O)OC BDJSOPWXYLFTNW-UHFFFAOYSA-N 0.000 description 1
- 229940057867 methyl lactate Drugs 0.000 description 1
- CWKLZLBVOJRSOM-UHFFFAOYSA-N methyl pyruvate Chemical compound COC(=O)C(C)=O CWKLZLBVOJRSOM-UHFFFAOYSA-N 0.000 description 1
- XJRBAMWJDBPFIM-UHFFFAOYSA-N methyl vinyl ether Chemical compound COC=C XJRBAMWJDBPFIM-UHFFFAOYSA-N 0.000 description 1
- 125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 229910000476 molybdenum oxide Inorganic materials 0.000 description 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PVWOIHVRPOBWPI-UHFFFAOYSA-N n-propyl iodide Chemical compound CCCI PVWOIHVRPOBWPI-UHFFFAOYSA-N 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- PCILLCXFKWDRMK-UHFFFAOYSA-N naphthalene-1,4-diol Chemical compound C1=CC=C2C(O)=CC=C(O)C2=C1 PCILLCXFKWDRMK-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N o-biphenylenemethane Natural products C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 150000002905 orthoesters Chemical class 0.000 description 1
- 125000003566 oxetanyl group Chemical group 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- PQQKPALAQIIWST-UHFFFAOYSA-N oxomolybdenum Chemical compound [Mo]=O PQQKPALAQIIWST-UHFFFAOYSA-N 0.000 description 1
- RVTZCBVAJQQJTK-UHFFFAOYSA-N oxygen(2-);zirconium(4+) Chemical compound [O-2].[O-2].[Zr+4] RVTZCBVAJQQJTK-UHFFFAOYSA-N 0.000 description 1
- XDEPVFFKOVDUNO-UHFFFAOYSA-N pentafluorobenzyl bromide Chemical compound FC1=C(F)C(F)=C(CBr)C(F)=C1F XDEPVFFKOVDUNO-UHFFFAOYSA-N 0.000 description 1
- 125000000538 pentafluorophenyl group Chemical group FC1=C(F)C(F)=C(*)C(F)=C1F 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 1
- CSHWQDPOILHKBI-UHFFFAOYSA-N peryrene Natural products C1=CC(C2=CC=CC=3C2=C2C=CC=3)=C3C2=CC=CC3=C1 CSHWQDPOILHKBI-UHFFFAOYSA-N 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- QLQOTPOBMXWKOW-UHFFFAOYSA-N phosphinothious acid Chemical compound SP QLQOTPOBMXWKOW-UHFFFAOYSA-N 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003227 poly(N-vinyl carbazole) Polymers 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920001083 polybutene Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 150000007519 polyprotic acids Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- FOWDZVNRQHPXDO-UHFFFAOYSA-N propyl hydrogen carbonate Chemical compound CCCOC(O)=O FOWDZVNRQHPXDO-UHFFFAOYSA-N 0.000 description 1
- RUOJZAUFBMNUDX-UHFFFAOYSA-N propylene carbonate Chemical compound CC1COC(=O)O1 RUOJZAUFBMNUDX-UHFFFAOYSA-N 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- 150000003902 salicylic acid esters Chemical class 0.000 description 1
- 229910052711 selenium Inorganic materials 0.000 description 1
- 239000011669 selenium Substances 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 230000000153 supplemental effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000003396 thiol group Chemical group [H]S* 0.000 description 1
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- CVNKFOIOZXAFBO-UHFFFAOYSA-J tin(4+);tetrahydroxide Chemical compound [OH-].[OH-].[OH-].[OH-].[Sn+4] CVNKFOIOZXAFBO-UHFFFAOYSA-J 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 125000005147 toluenesulfonyl group Chemical group C=1(C(=CC=CC1)S(=O)(=O)*)C 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- OPSWAWSNPREEFQ-UHFFFAOYSA-K triphenoxyalumane Chemical compound [Al+3].[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1.[O-]C1=CC=CC=C1 OPSWAWSNPREEFQ-UHFFFAOYSA-K 0.000 description 1
- BIKXLKXABVUSMH-UHFFFAOYSA-N trizinc;diborate Chemical compound [Zn+2].[Zn+2].[Zn+2].[O-]B([O-])[O-].[O-]B([O-])[O-] BIKXLKXABVUSMH-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C381/00—Compounds containing carbon and sulfur and having functional groups not covered by groups C07C301/00 - C07C337/00
- C07C381/12—Sulfonium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4064—Curing agents not provided for by the groups C08G59/42 - C08G59/66 sulfur containing compounds
-
- 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
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/68—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used
- C08G59/687—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the catalysts used containing sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerisation Methods In General (AREA)
Abstract
本發明提供一種硼酸鋶鹽,其不包含Sb等毒性高的元素,對熱或光等活性能量線具有高的感度,且在與環氧化合物等陽離子聚合性化合物的調配物中的貯存穩定性優異。本發明為通式(1)所表示的硼酸鋶鹽以及特徵在於含有該硼酸鋶鹽的酸產生劑等。 [式(1)中,R1
表示烷基,R2
表示下述通式(2)所表示的苄基]□
Description
本發明第一是有關於一種硼酸鋶鹽,第二是有關於一種酸產生劑,更詳細而言,是有關於含有當使熱或光、電子束或X射線等活性能量線發揮作用而使陽離子聚合性化合物硬化時適合的特定硼酸鋶鹽的酸產生劑。本發明第三是有關於含有該酸產生劑的硬化性組成物以及使其硬化而獲得的硬化體。
先前,使熱或光、電子束或X射線等活性能量線發揮作用而使環氧化合物等陽離子聚合性化合物硬化的陽離子聚合起始劑已知鋶鹽。
但,該些說明書中記載的陽離子聚合起始劑含有BF4 -
、PF6 -
、AsF6 -
、SbF6 -
作為陰離子,但陽離子聚合起始性能根據陰離子的種類而不同,以BF4 -
<PF6 -
<AsF6 -
<SbF6 -
的順序變得良好。但是,含有聚合起始能力良好的AsF6 -
、SbF6 -
的陽離子聚合起始劑由於As、Sb的毒性的問題,故而使用用途受到限定,SbF6 -
鹽僅可用於光造形等受到限定的用途。因此,通常利用聚合起始能力差的PF6 -
鹽,PF6 -
鹽為了獲得例如與SbF6 -
鹽相同程度的硬化速度,必須添加接近於後者的10倍的量,未反應的起始劑、為了將起始劑溶解而視需要使用的溶劑或者起始劑的分解物的殘存量變多,故而硬化物的物性受損,另外藉由起始劑的分解而副產生的HF量變多,因此存在基材或設備等容易腐蝕等問題。因此,強烈要求不包含毒性金屬且具有與SbF6 -
鹽匹敵的陽離子聚合起始能力的陽離子聚合起始劑。因此,近年來,代替SbF6 -
而將具有氟原子鍵結於碳原子上且包含硼原子的抗衡陰離子的硼酸鋶(sulfonium borate)鹽用作陽離子聚合起始劑。(專利文獻5、專利文獻6、專利文獻7、專利文獻8) [現有技術文獻] [專利文獻]
[專利文獻1]日本專利特開平2-196812 [專利文獻2]日本專利特開平3-17101 [專利文獻3]日本專利特開平3-237107 [專利文獻4]日本專利特開平3-205405 [專利文獻5]日本專利特開2008-303167 [專利文獻6]日本專利特開2010-132614 [專利文獻7]日本專利特開2012-153642 [專利文獻8]日本專利特開2010-201611
[發明所欲解決之課題]
專利文獻5~專利文獻8中記載的硼酸鋶鹽雖然對熱的活性優異,但具有以下缺點:缺乏室溫下的穩定性,與陽離子聚合性化合物的調配物的適用期短。
因此,本發明的第一目的為提供一種新的鋶鹽,其不包含Sb等毒性高的元素,且陽離子聚合能力以及與陽離子聚合性化合物的調配物的保存穩定性優異。 本發明的第二目的為提供一種新的酸產生劑,其是包含硼酸鋶鹽而成,所述硼酸鋶鹽不包含Sb等毒性高的元素,且陽離子聚合能力以及與陽離子聚合性化合物的調配物的保存穩定性優異。 本發明的第三目的為提供一種利用所述酸產生劑的硬化性組成物以及硬化體。 [解決課題之手段]
本發明者發現下述式(1)所表示的硼酸鋶鹽適合於所述目的。即,本發明提供式(1)所表示的硼酸鋶鹽。
[化1]
[式(1)中,R1
表示烷基,R2
表示下述通式(2)所表示的苄基]
[化2]
[式(2)中,R3
~R7
分別獨立地表示氫原子或者吸電子基,且表示R3
~R7
的哈米特取代基常數(Hammett substituent constant)σ值的合計為0.43以上者]
另外,本發明為一種酸產生劑,其特徵在於:含有所述硼酸鋶鹽。 另外,本發明為一種硬化性組成物,其是包含所述酸產生劑及陽離子聚合性化合物而成。 進而,本發明為一種硬化體,其特徵在於:使所述硬化性組成物硬化而獲得。 [發明的效果]
本發明的硼酸鋶鹽不包含Sb等毒性高的元素,且陽離子聚合能力以及與陽離子聚合性化合物的調配物的保存穩定性優異。
以下,對本發明的實施形態進行詳細說明。
式(1)中,R1
中的烷基可列舉:碳數1~18的直鏈烷基(甲基、乙基、正丙基、正丁基、正戊基、正辛基、正癸基、正十二烷基、正十四烷基、正十六烷基及正十八烷基等)、碳數1~18的分枝鏈烷基(異丙基、異丁基、第二丁基、第三丁基、異戊基、新戊基、第三戊基、異己基及異十八烷基)、以及碳數3~18的環烷基(環丙基、環丁基、環戊基、環己基及4-癸基環己基等)等。 該些烷基中,就反應性的觀點而言,較佳為碳數1~4的直鏈烷基,特佳為甲基。
式(1)中,R2
表示所述通式(2)所表示的苄基。式(2)中,R3
~R7
分別獨立地表示拉電子基,且表示R3
~R7
的哈米特取代基常數σ值的合計為0.43以上者。 R3
~R7
中的所謂吸電子基,於本發明中表示哈米特的取代基常數σ值為正值的取代基。關於哈米特的σ值,例如於都野雄甫的總論(有機合成化學第23卷第8號(1965)第631-642頁)、湯川泰秀翻譯的「克拉姆有機化學(Cram Organic Chemistry)[II]第4版」第656頁(廣川書店)等中有詳細說明。此外,本發明中將吸電子基由σ值來規定,但所述文獻中記載的已知值並非僅僅限定於某取代基。
σ值為正值的吸電子基可列舉:間烷氧基、間羥基、鹵素原子、鹵代烷基、醯氧基、醯基、氰基、硝基、磺醯基。所述R3
~R7
所表示的取代基只要以R3
~R7
的哈米特的取代基常數σ值的合計成為0.43以上的方式來選擇即可。 就貯存穩定性的觀點而言,R3
~R7
的哈米特的取代基常數σ值的合計較佳為0.70以上。上限通常為3.00以下,較佳為2.00以下。
所述吸電子基中的間烷氧基可列舉:間甲氧基、間乙氧基、間正丙氧基、間異丙氧基、間正丁氧基、間異丁氧基、間第三丁氧基等。 鹵素原子可列舉:氟原子、氯原子、溴原子及碘原子等。 鹵代烷基可列舉烷基中的氫原子的一部分或全部經氟原子取代的全氟烷基,該烷基可列舉:直鏈烷基(甲基、乙基、丙基、丁基、戊基及辛基等)、分枝鏈烷基(異丙基、異丁基、第二丁基及第三丁基等)以及環烷基(環丙基、環丁基、環戊基及環己基等)等。 醯氧基可列舉:乙醯氧基、丁醯氧基及苯甲醯氧基等。 醯基可列舉:乙醯基(acetyl)、乙醯基(ethanoyl)、丙醯基、丁醯基、三甲基乙醯基及苯甲醯基等。 磺醯基可列舉:甲磺醯基、苯磺醯基、甲苯磺醯基、三氟甲磺醯基及二氟甲磺醯基等。
R2
中,較佳為對硝基苄基、間硝基苄基、對氰基苄基、間氰基苄基、對三氟甲基苄基、間三氟甲基苄基、五氟苄基、3,5-雙(三氟甲基)苄基、2,4-雙(三氟甲基)苄基或者2,5-雙(三氟甲基)苄基。
本發明的硼酸鋶鹽的製造方法可依據以下的反應式來製造。 [化3]
此外,反應式中的R1
、R2
與式(1)中的定義相同。X表示鹵素原子,M+
表示鹼金屬(鋰、鈉及鉀等)陽離子。MX表示鹼金屬陽離子與鹵素陰離子的鹽。
所述反應式中,第一階段的反應可於無溶劑條件下進行,視需要亦可於水或有機溶媒、以及其混合物中進行。反應溫度雖亦取決於所使用的溶媒的沸點,但為-20℃~80℃左右。反應時間為1小時~數十小時左右。
第二階段的反應可繼第一階段的反應之後進行,亦可將鹵化鋶分離(視需要純化)後進行。將鹵化鋶、鹼金屬陽離子與四(五氟苯基)硼酸鹽的鹽的水溶液混合·攪拌,進行複分解反應,將析出的固體過濾分離,或者將分離的油狀物以有機溶媒萃取而去除有機溶媒,藉此以固體或黏稠的液體的形式獲得本發明的硼酸鋶鹽。所獲得的固體或者黏稠液體可視需要利用適當的有機溶媒進行洗滌,或者利用再結晶法或管柱層析法進行純化。
本發明的硼酸鋶鹽的化學結構可利用一般的分析方法(例如:1
H-、11
B-、13
C-、19
F-、31
P-核磁共振光譜、紅外吸收光譜及/或元素分析等)來鑑定。
本發明的硼酸鋶鹽適合作為酸產生劑。所謂酸產生劑是指藉由加熱或光照射,其化學結構分解而產生酸的化合物。所產生的酸可作為環氧化物的硬化反應等的觸媒來使用。
本發明的酸產生劑可直接使用本發明的硼酸鋶鹽,亦可使其中含有其他的酸產生劑來使用。
於含有其他的酸產生劑的情況下,相對於本發明的硼酸鋶鹽的總莫耳數,其他的酸產生劑的含量(莫耳%)較佳為1~100,尤佳為5~50。
其他的酸產生劑包含鎓鹽(鋶、錪鎓、硒鎓、銨及鏻等)以及過渡金屬錯合物離子與陰離子的鹽等現有公知的化合物。
本發明的酸產生劑為了容易溶解於陽離子聚合性化合物中,亦可預先溶解於不會阻礙陽離子聚合的溶劑中。
溶劑可列舉:碳酸伸丙酯、碳酸伸乙酯、碳酸-1,2-伸丁酯、碳酸二甲酯及碳酸二乙酯等碳酸酯類;丙酮、甲基乙基酮、環己酮、甲基異戊基酮、2-庚酮等酮類;乙二醇、乙二醇單乙酸酯、二乙二醇、二乙二醇單乙酸酯、丙二醇、丙二醇單乙酸酯、二丙二醇及二丙二醇單乙酸酯的單甲醚、單***、單丙醚、單丁醚、或者單苯基醚等多元醇類及其衍生物;二噁烷之類的環式醚類;甲酸乙酯、乳酸甲酯、乳酸乙酯、乙酸甲酯、乙酸乙酯、乙酸丁酯、丙酮酸甲酯、乙醯乙酸甲酯、乙醯乙酸乙酯、丙酮酸乙酯、乙氧基乙酸乙酯、甲氧基丙酸甲酯、乙氧基丙酸乙酯、2-羥基丙酸甲酯、2-羥基丙酸乙酯、2-羥基-2-甲基丙酸乙酯、2-羥基-3-甲基丁酸甲酯、3-甲氧基丁基乙酸酯、3-甲基-3-甲氧基丁基乙酸酯等酯類;甲苯、二甲苯等芳香族烴類等。
於使用溶劑的情況下,相對於本發明的酸產生劑100重量份,溶劑的使用比例較佳為15重量份~1000重量份,尤佳為30重量份~500重量份。所使用的溶媒可單獨使用,或者亦可將兩種以上併用。
本發明的硬化性組成物包含所述酸產生劑以及陽離子聚合性化合物。
陽離子聚合性化合物可列舉:環狀醚(環氧化物及氧雜環丁烷等)、乙烯性不飽和化合物(乙烯醚及苯乙烯等)、雙環原酸酯、螺環原碳酸酯及螺環原酸酯等(日本專利特開平11-060996號、日本專利特開平09-302269號、日本專利特開2003-026993號、日本專利特開2002-206017號、日本專利特開平11-349895號、日本專利特開平10-212343號、日本專利特開2000-119306號、日本專利特開平10-67812號、日本專利特開2000-186071號、日本專利特開平08-85775號、日本專利特開平08-134405號、日本專利特開2008-20838、日本專利特開2008-20839、日本專利特開2008-20841、日本專利特開2008-26660、日本專利特開2008-26644、日本專利特開2007-277327、光聚合物座談會編「光聚合物手冊」(1989年,工業調査會)、綜合技術中心編「UV·EB硬化技術」(1982年,綜合技術中心)、輻射固化(RadTech)研究會編「UV·EB硬化材料」(1992年,CMC)、技術資訊協會編「UV硬化中的硬化不良·阻礙原因及其對策」(2003年,技術資訊協會)、色材68(5)286-293(1995)、精細化學29(19)5-14(2000)等)。
環氧化物可使用公知者等,包含芳香族環氧化物、脂環式環氧化物以及脂肪族環氧化物。 芳香族環氧化物可列舉:具有至少一個芳香環的一元或多元的苯酚(苯酚、聯苯酚、雙酚A、雙酚F、苯酚酚醛清漆、甲酚酚醛清漆以及它們的溴化物或作為它們的環氧烷加成物的化合物)的縮水甘油醚、以及具有至少一個芳香環的一元或多元的羧酸(鄰苯二甲酸及3-甲基鄰苯二甲酸等)的縮水甘油酯(鄰苯二甲酸二縮水甘油酯以及鄰苯二甲酸二縮水甘油基-3-甲酯等)。
脂環式環氧化物可列舉:藉由將具有至少一個環己烯環或環戊烯環的化合物以氧化劑進行環氧化而獲得的化合物(3,4-環氧基環己烷羧酸-3,4-環氧基環己基甲酯等)。
脂肪族環氧化物可列舉:脂肪族多元醇或者作為其環氧烷加成物的聚縮水甘油醚(1,4-丁二醇二縮水甘油醚、1,6-己二醇二縮水甘油醚等)、脂肪族多元酸的聚縮水甘油酯(四氫鄰苯二甲酸二縮水甘油酯等)、長鏈不飽和化合物的環氧化物(環氧化大豆油以及環氧化聚丁二烯等)。
氧雜環丁烷可使用公知者等,例如可列舉:3-乙基-3-羥基甲基氧雜環丁烷、2-乙基己基(3-乙基-3-氧雜環丁基甲基)醚、2-羥基乙基(3-乙基-3-氧雜環丁基甲基)醚、2-羥基丙基(3-乙基-3-氧雜環丁基甲基)醚、1,4-雙[(3-乙基-3-氧雜環丁基甲氧基)甲基]苯、氧雜環丁基倍半矽氧烷以及苯酚酚醛清漆氧雜環丁烷等。
乙烯性不飽和化合物可使用公知的陽離子聚合性單量體等,包含:脂肪族單乙烯醚、芳香族單乙烯醚、多官能乙烯醚、苯乙烯以及陽離子聚合性含氮單體。
脂肪族單乙烯醚可列舉:甲基乙烯醚、乙基乙烯醚、丁基乙烯醚以及環己基乙烯醚等。
芳香族單乙烯醚可列舉:2-苯氧基乙基乙烯醚、苯基乙烯醚以及對甲氧基苯基乙烯醚等。
多官能乙烯醚可列舉:丁二醇-1,4-二乙烯醚以及三乙二醇二乙烯醚等。
苯乙烯可列舉:苯乙烯、α-甲基苯乙烯、對甲氧基苯乙烯以及對第三丁氧基苯乙烯等。
陽離子聚合性含氮單體可列舉:N-乙烯基咔唑以及N-乙烯基吡咯啶酮等。
雙環原酸酯可列舉:1-苯基-4-乙基-2,6,7-三氧雜雙環[2.2.2]辛烷以及1-乙基-4-羥基甲基-2,6,7-三氧雜雙環-[2.2.2]辛烷等。
螺環原碳酸酯可列舉:1,5,7,11-四氧雜螺環[5.5]十一烷以及3,9-二苄基-1,5,7,11-四氧雜螺環[5.5]十一烷等。
螺環原酸酯可列舉:1,4,6-三氧雜螺環[4.4]壬烷、2-甲基-1,4,6-三氧雜螺環[4.4]壬烷以及1,4,6-三氧雜螺環[4.5]癸烷等。
該些陽離子聚合性化合物中,較佳為環氧化物、氧雜環丁烷以及乙烯醚,尤佳為環氧化物以及氧雜環丁烷,特佳為脂環式環氧化物以及氧雜環丁烷。另外,該些陽離子聚合性化合物可單獨使用,或者亦可將兩種以上併用。
相對於陽離子聚合性化合物100份,硬化性組成物中的本發明的酸產生劑的含量較佳為0.05重量份~20重量份,尤佳為0.1重量份~10重量份。若為該範圍,則陽離子聚合性化合物的聚合變得更充分,硬化體的物性變得更良好。此外,該含量是藉由考慮陽離子聚合性化合物的性質或能量線的種類及照射量、溫度、硬化時間、濕度、塗膜的厚度等各種因素來決定,並不限定於所述範圍。
本發明的硬化性組成物中,可視需要而含有公知的添加劑(增感劑、顏料、填充劑、抗靜電劑、阻燃劑、消泡劑、流動調整劑、光穩定劑、抗氧化劑、密合性賦予劑、離子補充劑、防著色劑、溶劑、非反應性的樹脂以及自由基聚合性化合物等)。
本發明的硬化性組成物中基本上不需要增感劑,但可視需要而含有增感劑來作為補充硬化性者。此種增感劑可使用公知(日本專利特開平11-279212號以及日本專利特開平09-183960號等)的增感劑等,可列舉:蒽{蒽、9,10-二丁氧基蒽、9,10-二甲氧基蒽、9,10-二乙氧基蒽、2-乙基-9,10-二甲氧基蒽、9,10-二丙氧基蒽等};芘(pyrene);1,2-苯并蒽(1,2-benzanthracene);苝(perylene);稠四苯;蔻(coronene);硫雜蒽酮(thioxanthone){硫雜蒽酮、2-甲基硫雜蒽酮、2-乙基硫雜蒽酮、2-氯硫雜蒽酮、2-異丙基硫雜蒽酮以及2,4-二乙基硫雜蒽酮等};啡噻嗪(phenothiazine){啡噻嗪、N-甲基啡噻嗪、N-乙基啡噻嗪、N-苯基啡噻嗪等};氧雜蒽酮(xanthone);萘(naphthalene){1-萘酚(1-naphthol)、2-萘酚、1-甲氧基萘、2-甲氧基萘、1,4-二羥基萘、以及4-甲氧基-1-萘酚等};酮{二甲氧基苯乙酮、二乙氧基苯乙酮、2-羥基-2-甲基-1-苯基丙烷-1-酮、4'-異丙基-2-羥基-2-甲基苯丙酮以及4-苯甲醯基-4'-甲基二苯基硫醚等};咔唑(carbazole){N-苯基咔唑、N-乙基咔唑、聚-N-乙烯基咔唑以及N-縮水甘油基咔唑等};(chrysene){1,4-二甲氧基以及1,4-二-α-甲基苄氧基等};菲(phenanthrene){9-羥基菲、9-甲氧基菲、9-羥基-10-甲氧基菲以及9-羥基-10-乙氧基菲等}等。
於含有增感劑的情況下,相對於酸產生劑100份,增感劑的含量較佳為1重量份~300重量份,尤佳為5重量份~200重量份。
顏料可使用公知的顏料等,可列舉:無機顏料(氧化鈦、氧化鐵及碳黑等)以及有機顏料(偶氮顏料、花青顏料、酞菁顏料及喹吖啶酮(quinacridone)顏料等)等。
於含有顏料的情況下,相對於酸產生劑100份,顏料的含量較佳為0.5重量份~400000重量份,尤佳為10重量份~150000重量份。
填充劑可使用公知的填充劑等,可列舉:熔融二氧化矽、結晶二氧化矽、碳酸鈣、氧化鋁、氫氧化鋁、氧化鋯、碳酸鎂、雲母、滑石、矽酸鈣及矽酸鋰鋁等。
於含有填充劑的情況下,相對於酸產生劑100份,填充劑的含量較佳為50重量份~600000重量份,尤佳為300重量份~200000重量份。
抗靜電劑可使用公知的抗靜電劑等,可列舉:非離子型抗靜電劑、陰離子型抗靜電劑、陽離子型抗靜電劑、兩性型抗靜電劑以及高分子型抗靜電劑。
於含有抗靜電劑的情況下,相對於酸產生劑100份,抗靜電劑的含量較佳為0.1重量份~20000重量份,尤佳為0.6重量份~5000重量份。
阻燃劑可使用公知的阻燃劑等,可列舉:無機阻燃劑{三氧化銻、五氧化銻、氧化錫、氫氧化錫、氧化鉬、硼酸鋅、偏硼酸鋇、紅磷、氫氧化鋁、氫氧化鎂及鋁酸鈣等};溴阻燃劑{四溴鄰苯二甲酸酐、六溴苯以及十溴聯苯基醚等};以及磷酸酯阻燃劑{三(三溴苯基)磷酸酯等}等。
於含有阻燃劑的情況下,相對於酸產生劑100份,阻燃劑的含量較佳為0.5重量份~40000重量份,尤佳為5重量份~10000重量份。
消泡劑可使用公知的消泡劑等,可列舉:醇消泡劑、金屬皂消泡劑、磷酸酯消泡劑、脂肪酸酯消泡劑、聚醚消泡劑、矽酮消泡劑以及礦物油消泡劑等。
流動調整劑可使用公知的流動性調整劑等,可列舉:氫化蓖麻油、氧化聚乙烯、有機膨土、膠體狀二氧化矽、醯胺蠟(amide wax)、金屬皂及丙烯酸酯聚合物等。 光穩定劑可使用公知的光穩定劑等,可列舉:紫外線吸收型穩定劑{苯并***、二苯甲酮、水楊酸酯、氰基丙烯酸酯以及它們的衍生物等};自由基補充型穩定劑{受阻胺等};以及消光型穩定劑{鎳錯合物等}等。 抗氧化劑可使用公知的抗氧化劑等,可列舉:酚系抗氧化劑(單酚系、雙酚系及高分子酚系等)、硫系抗氧化劑及磷系抗氧化劑等。 密合性賦予劑可使用公知的密合性賦予劑等,可列舉:偶合劑、矽烷偶合劑及鈦偶合劑等。 離子補充劑可使用公知的離子補充劑等,可列舉:有機鋁(烷氧基鋁以及苯氧基鋁等)等。 防著色劑可使用公知的防著色劑,通常有效的是抗氧化劑,可列舉:酚系抗氧化劑(單酚系、雙酚系及高分子酚系等)、硫系抗氧化劑以及磷系抗氧化劑等。
於含有消泡劑、流動調整劑、光穩定劑、抗氧化劑、密合性賦予劑、離子補充劑或者防著色劑的情況下,相對於酸產生劑100份,各自的含量較佳為0.1重量份~20000重量份,尤佳為0.5重量份~5000重量份。
溶劑只要可用於溶解陽離子聚合性化合物或調整硬化性組成物的黏度,則並無限制,可使用作為所述酸產生劑的溶劑而列舉者。
於含有溶劑的情況下,相對於酸產生劑100份,溶劑的含量較佳為50重量份~2000000重量份,尤佳為200重量份~500000重量份。
非反應性的樹脂可列舉:聚酯、聚乙酸乙烯酯、聚氯乙烯、聚丁二烯、聚碳酸酯、聚苯乙烯、聚乙烯醚、聚乙烯基丁醛、聚丁烯、苯乙烯丁二烯嵌段共聚物氫化物、(甲基)丙烯酸酯的共聚物以及聚胺基甲酸酯等。該些樹脂的數量平均分子量較佳為1000~500000,尤佳為5000~100000(數量平均分子量為利用凝膠滲透層析法(gel permeation chromatography,GPC)等一般的方法來測定的值)。
於含有非反應性的樹脂的情況下,相對於酸產生劑100份,非反應性的樹脂的含量較佳為5重量份~400000重量份,尤佳為50重量份~150000重量份。
於含有非反應性的樹脂的情況下,為了容易將非反應性的樹脂與陽離子聚合性化合物等溶解,理想為預先溶解於溶劑中。
自由基聚合性化合物可使用:公知{光聚合物座談會編「光聚合物手冊」(1989年,工業調査會)、綜合技術中心編「UV·EB硬化技術」(1982年,綜合技術中心)、輻射固化(RadTech)研究會編「UV·EB硬化材料」(1992年,CMC)、技術資訊協會編「UV硬化中的硬化不良·阻礙原因及其對策」(2003年,技術資訊協會)}的自由基聚合性化合物等,包含:單官能單體、二官能單體、多官能單體、環氧基(甲基)丙烯酸酯、聚酯(甲基)丙烯酸酯及胺基甲酸酯(甲基)丙烯酸酯。
於含有自由基聚合性化合物的情況下,相對於酸產生劑100份,自由基聚合性化合物的含量較佳為5重量份~400000重量份,尤佳為50重量份~150000重量份。
於含有自由基聚合性化合物的情況下,為了藉由自由基聚合使該些自由基聚合性化合物進行高分子量化,較佳為使用藉由熱或光而引發聚合的自由基聚合起始劑。
自由基聚合起始劑可使用公知的自由基聚合起始劑等,包含:熱自由基聚合起始劑(有機過氧化物、偶氮化合物等)以及光自由基聚合起始劑(苯乙酮系起始劑、二苯甲酮系起始劑、米其勒酮系起始劑、安息香系起始劑、硫雜蒽酮系起始劑、醯基膦系起始劑等)。
於含有自由基聚合起始劑的情況下,相對於自由基聚合性化合物100份,自由基聚合起始劑的含量較佳為0.01重量份~20重量份,尤佳為0.1重量份~10重量份。
本發明的硬化性組成物可將陽離子聚合性化合物、酸產生劑以及視需要的添加劑於室溫(20℃~30℃左右)或者視需要於加熱(40℃~90℃左右)下,均勻地混合溶解,或者進而利用三輥機等進行混煉來製備。
本發明的硬化性組成物可藉由加熱或者照射能量線而硬化以獲得硬化體。 能量線只要具有誘發本發明的硼酸鋶鹽的分解的能量,則可為任一者,較佳為由低壓、中壓、高壓或超高壓的水銀燈,金屬鹵化物燈、發光二極體(light emitting diode,LED)燈、氙燈、碳弧燈、螢光燈、半導體固體雷射、氬雷射、He-Cd雷射、KrF準分子雷射、ArF準分子雷射或者F2
雷射等而獲得的紫外~可見光區域(波長:約100 nm~約800 nm)的能量線。此外,能量線中亦可使用電子束或者X射線等具有高能量的放射線。
能量線的照射時間受到能量線的強度或能量線對硬化性組成物的透過性的影響,但充分的是常溫(20℃~30℃左右)下、0.1秒~10秒左右。但是,於能量線的透過性低的情況下或硬化性組成物的膜厚較厚的情況下等,有時較佳為施加其以上的時間。於能量線照射後0.1秒~數分鐘後,大部分的硬化性組成物藉由陽離子聚合而硬化,但如有必要,亦可於能量線的照射後,於室溫(20℃~30℃左右)~150℃下加熱數秒~數小時而進行後硬化。
用以進行硬化的加熱方法例如可使用熱循環式加熱、紅外線加熱、高頻加熱等現有公知的方法。
硬化所需要的加熱溫度若為硬化充分進行,不會使基材劣化的範圍,則並無特別限定,較佳為50℃至250℃,更佳為80℃至200℃的範圍,加熱時間雖依存於加熱溫度,但就生產性的方面而言,較佳為數分鐘至數小時。
本發明的硬化性組成物的具體用途可列舉:塗料、塗佈劑、墨水、噴墨墨水、正型抗蝕劑、抗蝕劑膜、液狀抗蝕劑、負型抗蝕劑、微機電系統(Micro-Electro-Mechanical System,MEMS)用抗蝕劑、正型感光性材料、負型感光性材料、各種黏接劑、成形材料、澆鑄材料、油灰(putty)、玻璃纖維含浸劑、填充材料、密封(sealing)材料、密閉材料、光半導體(LED)密閉材料、光波導材料、奈米壓印材料、光造用以及微光造形用材料等。 [實施例]
以下,藉由實施例來對本發明進一步進行說明,但本發明並不意圖限定於此。此外,以下只要無特別記載,則份是指重量份,%是指重量%。
[製造例1] 4-(乙基硫基)苯酚的合成 使5.00 g(0.04莫耳)的4-羥基苯硫醇、6.18 g(0.04莫耳)的碘乙烷溶解於20 ml的丙酮中,添加6.02 g(0.44莫耳)的碳酸鉀,於40℃下進行10小時反應。反應後,添加20 ml的乙酸乙酯,利用50 ml的離子交換水來洗滌3次,去除溶媒,藉此獲得4.84 g的4-(乙基硫基)苯酚。
[製造例2] 4-(丙基硫基)苯酚的合成 代替6.18 g的碘乙烷而使用6.62 g的碘丙烷,依據製造例1中記載的方法來合成。
[製造例3] 4-(丁基硫基)苯酚的合成 代替6.18 g的碘乙烷而使用7.29 g的碘丁烷,依據製造例1中記載的方法來合成。
[實施例1] 酸產生劑A-1的合成 使2.16 g(0.01莫耳)的對硝基苄基溴、1.40 g(0.01莫耳)的4-(甲基硫基)苯酚溶解於15 ml的甲醇中,於50℃下攪拌12小時。添加30 ml的離子交換水、15 ml的乙酸乙酯,攪拌30分鐘後進行分液,去除乙酸乙酯層。將於水層中包含等莫耳的四(五氟苯基)硼酸鈉的水溶液70 g、30 ml的乙酸乙酯於室溫下混合,直接攪拌3小時。藉由分液操作,將乙酸乙酯層以水洗滌3次後,利用旋轉蒸發器來蒸餾去除溶媒,藉此獲得8.22 g的白色固體。藉由1H-核磁共振(nuclear magnetic resonance,NMR)來確認該白色固體為酸產生劑A-1。A-1的結構記載於表1中。
[實施例2] 酸產生劑A-2的合成 代替2.16 g的對硝基苄基溴而使用2.16 g的間硝基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-2的結構記載於表1中。
[實施例3] 酸產生劑A-3的合成 代替2.16 g的對硝基苄基溴而使用1.96 g的對氰基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-3的結構記載於表1中。
[實施例4] 酸產生劑A-4的合成 代替2.16 g的對硝基苄基溴而使用1.96 g的間氰基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-4的結構記載於表1中。
[實施例5] 酸產生劑A-5的合成 代替2.16 g的對硝基苄基溴而使用2.39 g的對三氟甲基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-5的結構記載於表1中。
[實施例6] 酸產生劑A-6的合成 代替2.16 g的對硝基苄基溴而使用2.39 g的間三氟甲基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-6的結構記載於表1中。
[實施例7] 酸產生劑A-7的合成 代替2.16 g的對硝基苄基溴而使用2.61 g的五氟苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-7的結構記載於表1中。
[實施例8] 酸產生劑A-8的合成 代替2.16 g的對硝基苄基溴而使用3.07 g的3,5-三氟甲基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-8的結構記載於表1中。
[實施例9] 酸產生劑A-9的合成 代替2.16 g的對硝基苄基溴而使用3.07 g的2,4-三氟甲基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-9的結構記載於表1中。
[實施例10] 酸產生劑A-10的合成 代替2.16 g的對硝基苄基溴而使用3.07 g的2,5-三氟甲基苄基溴,依據實施例1中記載的方法來製備。酸產生劑A-10的結構記載於表1中。
[實施例11] 酸產生劑A-11的合成 代替1.40 g的4-(甲基硫基)苯酚而使用1.54 g的製造例1中合成的4-(乙基硫基)苯酚,依據實施例1中記載的方法來製備。酸產生劑A-11的結構記載於表1中。
[實施例12] 酸產生劑A-12的合成 代替1.40 g的4-(甲基硫基)苯酚而使用1.65 g的製造例2中合成的4-(丙基硫基)苯酚,依據實施例1中記載的方法來製備。酸產生劑A-12的結構記載於表1中。
[實施例13] 酸產生劑A-13的合成 代替1.40 g的4-(甲基硫基)苯酚而使用1.82 g的製造例3中合成的4-(丁基硫基)苯酚,依據實施例1中記載的方法來製備。酸產生劑A-13的結構記載於表1中。
[比較例1] 酸產生劑H-1的合成 代替2.16 g的對硝基苄基溴而使用1.27 g的苄基氯,依據實施例1中記載的方法來製備。酸產生劑H-1的結構記載於表1中。
[比較例2] 酸產生劑H-2的合成 代替2.16 g的對硝基苄基溴而使用1.45 g的對氟苄基氯,依據實施例1中記載的方法來製備。酸產生劑H-2的結構記載於表1中。
[比較例3] 酸產生劑H-3的合成 代替2.16 g的對硝基苄基溴而使用1.61 g的對氯苄基氯,依據實施例1中記載的方法來製備。酸產生劑H-3的結構記載於表1中。
[比較例4] 酸產生劑H-4的合成 代替2.16 g的對硝基苄基溴而使用2.50 g的對溴苄基溴,依據實施例1中記載的方法來製備。酸產生劑H-4的結構記載於表1中。
[比較例5] 四(五氟苯基)硼酸-4-羥基苯基二甲基鋶(H-5)的合成 使1.92 g(0.01莫耳)的氯化-4-羥基苯基二甲基鋶溶解於15 ml的二氯甲烷中,將於水層中包含等莫耳的四(五氟苯基)硼酸鈉的水溶液等70 g於室溫下混合,直接攪拌3小時。藉由分液操作,將二氯甲烷層以水洗滌3次後,轉移至旋轉蒸發器中而蒸餾去除溶媒,藉此獲得四(五氟苯基)硼酸-4-羥基苯基二甲基鋶。
[比較例6] 四(五氟苯基)硼酸-4-乙醯氧基苯基二甲基鋶(H-6)的合成 使比較例5中合成的6.00 g(0.01莫耳)的四(五氟苯基)硼酸-4-羥基苯基二甲基鋶溶解於100 ml的乙腈中,於10℃以下添加1.22 g(0.012莫耳)的三乙基胺,於30分鐘後,滴加0.95 g(0.012莫耳)的乙醯氯。攪拌3小時後,將副產生的三乙基胺的鹽酸鹽過濾去除,轉移至旋轉蒸發器中而蒸餾去除溶媒,藉此獲得四(五氟苯基)硼酸-4-乙醯氧基苯基二甲基鋶。
[表1]
(熱硬化性組成物的製備以及其評價) 將本發明的酸產生劑以及比較例的化合物以表2所示的調配量溶解於碳酸伸丙酯中後,以表2的調配量(重量份)均勻混合於作為陽離子聚合性化合物的環氧化物(雙酚A型環氧樹脂,日本環氧樹脂(Japan epoxy resin)公司製造,埃皮考特(Epikote)828)中,製備熱硬化性組成物(實施例C1~實施例C10、比較例C1~比較例C6)。
[表2]
<凝膠時間(熱硬化性)> 對於所述獲得的熱硬化性組成物,依據JISK5909的方法來測定凝膠時間。 將該些結果示於表3中。
<貯存穩定性> 將所述獲得的熱硬化性組成物於遮光下、40℃下保存1週後,測定調配試樣的黏度,藉由下述基準進行評價。將該些結果示於表3中。 (評價基準) ×:1週後的黏度變化為2.0倍以上。 ○:1週後的黏度變化小於2.0倍。 ◎:2週後的黏度變化小於2.0倍。
[表3]
如表3的結果所明示,可知與比較用的硼酸鋶鹽相比,本發明的硼酸鋶鹽的熱硬化性及貯存穩定性的平衡優異。 [產業上之可利用性]
本發明的硼酸鋶鹽適合用作以下材料中使用的酸產生劑:塗料、塗佈劑、墨水、噴墨墨水、正型抗蝕劑(電路基板、晶片尺寸封裝(Chip Scale Package,CSP)、MEMS元件等電子零件製造的連接端子或配線圖案形成等)、抗蝕劑膜、液狀抗蝕劑、負型抗蝕劑(半導體元件等的表面保護膜、層間絕緣膜、平坦化膜等永久膜材料等)、MEMS用抗蝕劑、感光性材料、各種黏接劑、成形材料、澆鑄材料、油灰、玻璃纖維含浸劑、填充材料、密封(sealing)材料、密閉材料、光半導體(LED)密閉材料、奈米壓印材料、光造用、微光造形用材料等。
無
無
無
Claims (5)
- 一種硼酸鋶鹽,其是由下述通式(1)所表示,[式(1)中,R1 表示烷基,R2 表示下述通式(2)所表示的苄基][式(2)中,R3 ~R7 分別獨立地表示氫原子或者吸電子基,且表示R3 ~R7 的哈米特取代基常數σ值的合計為0.43以上者]。
- 如申請專利範圍第1項所述的硼酸鋶鹽,其中式(1)中的R2 為對硝基苄基、間硝基苄基、對氰基苄基、間氰基苄基、對三氟甲基苄基、間三氟甲基苄基、五氟苄基、3,5-雙(三氟甲基)苄基、2,4-雙(三氟甲基)苄基、2,5-雙(三氟甲基)苄基的任一者。
- 一種酸產生劑,其特徵在於:含有如申請專利範圍第1項或第2項所述的硼酸鋶鹽。
- 一種硬化性組成物,其是包含如申請專利範圍第3項所述的酸產生劑及陽離子聚合性化合物而成。
- 一種硬化體,其特徵在於:使如申請專利範圍第4項所述的硬化性組成物硬化而獲得。
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