CN113402665A - 包含高溶解性光致酸产生剂的牙科用光固化性组合物 - Google Patents
包含高溶解性光致酸产生剂的牙科用光固化性组合物 Download PDFInfo
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- CN113402665A CN113402665A CN202110276469.8A CN202110276469A CN113402665A CN 113402665 A CN113402665 A CN 113402665A CN 202110276469 A CN202110276469 A CN 202110276469A CN 113402665 A CN113402665 A CN 113402665A
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- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001791 phenazinyl group Chemical group C1(=CC=CC2=NC3=CC=CC=C3N=C12)* 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 description 1
- 125000001484 phenothiazinyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3NC12)* 0.000 description 1
- 125000004932 phenoxathinyl group Chemical group 0.000 description 1
- 125000001644 phenoxazinyl group Chemical group C1(=CC=CC=2OC3=CC=CC=C3NC12)* 0.000 description 1
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 1
- 125000006678 phenoxycarbonyl group Chemical group 0.000 description 1
- RAFRTSDUWORDLA-UHFFFAOYSA-N phenyl 3-chloropropanoate Chemical compound ClCCC(=O)OC1=CC=CC=C1 RAFRTSDUWORDLA-UHFFFAOYSA-N 0.000 description 1
- NPUSTSBKXOLJIC-UHFFFAOYSA-N phenyl(2-prop-2-enoyloxyethoxy)phosphinic acid Chemical compound C=CC(=O)OCCOP(=O)(C1=CC=CC=C1)O NPUSTSBKXOLJIC-UHFFFAOYSA-N 0.000 description 1
- 125000003356 phenylsulfanyl group Chemical group [*]SC1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 125000003170 phenylsulfonyl group Chemical group C1(=CC=CC=C1)S(=O)(=O)* 0.000 description 1
- 125000002467 phosphate group Chemical group [H]OP(=O)(O[H])O[*] 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920006393 polyether sulfone Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- DJEHXEMURTVAOE-UHFFFAOYSA-M potassium bisulfite Chemical compound [K+].OS([O-])=O DJEHXEMURTVAOE-UHFFFAOYSA-M 0.000 description 1
- 229940099427 potassium bisulfite Drugs 0.000 description 1
- 235000010259 potassium hydrogen sulphite Nutrition 0.000 description 1
- 235000010289 potassium nitrite Nutrition 0.000 description 1
- 239000004304 potassium nitrite Substances 0.000 description 1
- BHZRJJOHZFYXTO-UHFFFAOYSA-L potassium sulfite Chemical compound [K+].[K+].[O-]S([O-])=O BHZRJJOHZFYXTO-UHFFFAOYSA-L 0.000 description 1
- 235000019252 potassium sulphite Nutrition 0.000 description 1
- NLZLDWFYQXFPSZ-UHFFFAOYSA-M potassium;2,4,6-triethylbenzenesulfinate Chemical compound [K+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 NLZLDWFYQXFPSZ-UHFFFAOYSA-M 0.000 description 1
- SCRWQCKSJIHKKV-UHFFFAOYSA-M potassium;2,4,6-trimethylbenzenesulfinate Chemical compound [K+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 SCRWQCKSJIHKKV-UHFFFAOYSA-M 0.000 description 1
- YVHWGMMGEAQQRT-UHFFFAOYSA-M potassium;4-methylbenzenesulfinate Chemical compound [K+].CC1=CC=C(S([O-])=O)C=C1 YVHWGMMGEAQQRT-UHFFFAOYSA-M 0.000 description 1
- LZSBNSVOXWMXLL-UHFFFAOYSA-M potassium;benzenesulfinate Chemical compound [K+].[O-]S(=O)C1=CC=CC=C1 LZSBNSVOXWMXLL-UHFFFAOYSA-M 0.000 description 1
- 150000003139 primary aliphatic amines Chemical class 0.000 description 1
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000004742 propyloxycarbonyl group Chemical group 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 125000003373 pyrazinyl group Chemical group 0.000 description 1
- 125000001725 pyrenyl group Chemical group 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 125000000168 pyrrolyl group Chemical group 0.000 description 1
- 125000002294 quinazolinyl group Chemical group N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 125000005493 quinolyl group Chemical group 0.000 description 1
- 125000001567 quinoxalinyl group Chemical group N1=C(C=NC2=CC=CC=C12)* 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 238000005057 refrigeration Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000003829 resin cement Substances 0.000 description 1
- HUIHCQPFSRNMNM-UHFFFAOYSA-K scandium(3+);triiodide Chemical compound [Sc+3].[I-].[I-].[I-] HUIHCQPFSRNMNM-UHFFFAOYSA-K 0.000 description 1
- 125000005930 sec-butyloxycarbonyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(OC(*)=O)C([H])([H])[H] 0.000 description 1
- VSZWPYCFIRKVQL-UHFFFAOYSA-N selanylidenegallium;selenium Chemical compound [Se].[Se]=[Ga].[Se]=[Ga] VSZWPYCFIRKVQL-UHFFFAOYSA-N 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 230000008313 sensitization Effects 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 229940077386 sodium benzenesulfonate Drugs 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 235000010288 sodium nitrite Nutrition 0.000 description 1
- 235000010265 sodium sulphite Nutrition 0.000 description 1
- VMMZJFAHOAKUQM-UHFFFAOYSA-N sodium;1,3,5-trimethyl-1,3-diazinane-2,4,6-trione Chemical compound [Na].CC1C(=O)N(C)C(=O)N(C)C1=O VMMZJFAHOAKUQM-UHFFFAOYSA-N 0.000 description 1
- VFTILSBBLXWMQK-UHFFFAOYSA-M sodium;1-cyclohexyl-5-ethyl-4,6-dioxopyrimidin-2-olate Chemical compound [Na+].O=C1C(CC)C(=O)[N-]C(=O)N1C1CCCCC1 VFTILSBBLXWMQK-UHFFFAOYSA-M 0.000 description 1
- KNHRGMOGYVTHPU-UHFFFAOYSA-M sodium;2,4,6-triethylbenzenesulfinate Chemical compound [Na+].CCC1=CC(CC)=C(S([O-])=O)C(CC)=C1 KNHRGMOGYVTHPU-UHFFFAOYSA-M 0.000 description 1
- GRBCNEIBDFNEES-UHFFFAOYSA-M sodium;2,4,6-trimethylbenzenesulfinate Chemical compound [Na+].CC1=CC(C)=C(S([O-])=O)C(C)=C1 GRBCNEIBDFNEES-UHFFFAOYSA-M 0.000 description 1
- CHLCPTJLUJHDBO-UHFFFAOYSA-M sodium;benzenesulfinate Chemical compound [Na+].[O-]S(=O)C1=CC=CC=C1 CHLCPTJLUJHDBO-UHFFFAOYSA-M 0.000 description 1
- MZSDGDXXBZSFTG-UHFFFAOYSA-M sodium;benzenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC=CC=C1 MZSDGDXXBZSFTG-UHFFFAOYSA-M 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000001179 sorption measurement Methods 0.000 description 1
- BGKZULDOBMANRY-UHFFFAOYSA-N sulfanyl prop-2-enoate Chemical compound SOC(=O)C=C BGKZULDOBMANRY-UHFFFAOYSA-N 0.000 description 1
- BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
- 150000003455 sulfinic acids Chemical class 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003419 tautomerization reaction Methods 0.000 description 1
- 230000002123 temporal effect Effects 0.000 description 1
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 125000005931 tert-butyloxycarbonyl group Chemical group [H]C([H])([H])C(OC(*)=O)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 125000001935 tetracenyl group Chemical group C1(=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C12)* 0.000 description 1
- 125000004627 thianthrenyl group Chemical group C1(=CC=CC=2SC3=CC=CC=C3SC12)* 0.000 description 1
- 125000000335 thiazolyl group Chemical group 0.000 description 1
- DHCDFWKWKRSZHF-UHFFFAOYSA-L thiosulfate(2-) Chemical compound [O-]S([S-])(=O)=O DHCDFWKWKRSZHF-UHFFFAOYSA-L 0.000 description 1
- GWIKYPMLNBTJHR-UHFFFAOYSA-M thiosulfonate group Chemical group S(=S)(=O)[O-] GWIKYPMLNBTJHR-UHFFFAOYSA-M 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- XJDNKRIXUMDJCW-UHFFFAOYSA-J titanium tetrachloride Chemical compound Cl[Ti](Cl)(Cl)Cl XJDNKRIXUMDJCW-UHFFFAOYSA-J 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 230000036367 tooth discoloration Effects 0.000 description 1
- 125000002088 tosyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])S(*)(=O)=O 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000004360 trifluorophenyl group Chemical group 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- RMZAYIKUYWXQPB-UHFFFAOYSA-N trioctylphosphane Chemical compound CCCCCCCCP(CCCCCCCC)CCCCCCCC RMZAYIKUYWXQPB-UHFFFAOYSA-N 0.000 description 1
- BZVJOYBTLHNRDW-UHFFFAOYSA-N triphenylmethanamine Chemical compound C=1C=CC=CC=1C(C=1C=CC=CC=1)(N)C1=CC=CC=C1 BZVJOYBTLHNRDW-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- GEPJPYNDFSOARB-UHFFFAOYSA-N tris(4-fluorophenyl)phosphane Chemical compound C1=CC(F)=CC=C1P(C=1C=CC(F)=CC=1)C1=CC=C(F)C=C1 GEPJPYNDFSOARB-UHFFFAOYSA-N 0.000 description 1
- UYUUAUOYLFIRJG-UHFFFAOYSA-N tris(4-methoxyphenyl)phosphane Chemical compound C1=CC(OC)=CC=C1P(C=1C=CC(OC)=CC=1)C1=CC=C(OC)C=C1 UYUUAUOYLFIRJG-UHFFFAOYSA-N 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 238000003466 welding Methods 0.000 description 1
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 239000004246 zinc acetate Substances 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- SCWPFSIZUZUCCE-UHFFFAOYSA-N β-terpinene Chemical compound CC(C)C1=CCC(=C)CC1 SCWPFSIZUZUCCE-UHFFFAOYSA-N 0.000 description 1
Classifications
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/10—Esters
- C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
- C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/15—Compositions characterised by their physical properties
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/30—Compositions for temporarily or permanently fixing teeth or palates, e.g. primers for dental adhesives
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
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- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
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- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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- C08K3/34—Silicon-containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
本发明提供从低温恢复到室温后也能够表现出优异的机械物理性质的牙科用光固化性组合物。该牙科用光固化性组合物包含(A)聚合性单体、(B)光敏剂、(C)光致酸产生剂以及(D)光聚合促进剂,(C)光致酸产生剂包含(C‑1)与logS为‑4以下的阴离子形成的碘鎓盐系化合物。
Description
技术领域
本发明涉及牙科用光固化性组合物。
背景技术
在牙科领域中口腔内的治疗中使用牙科用光固化性组合物,其应用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用玻璃离子水门汀、牙科用切削加工用材料、牙科用3D打印用材料等。
在日本特许4093974号公报中,作为光聚合引发剂提出了含有光致酸产生剂(三嗪化合物或特定的芳基碘鎓盐)、增敏剂和供电子化合物而成的光聚合引发剂。
在日本特许4596786号公报中,作为光聚合引发剂提出了含有光致酸产生剂(三嗪化合物或特定的芳基碘鎓盐)、增敏剂和供电子化合物而成的光聚合引发剂。
发明内容
但是,使用日本特许4093974号公报和日本特许4596786号公报记载的以往的光聚合引发剂的牙科用光固化性组合物在低温保管后不能获得充分的物理性质。
本发明的目的在于提供从低温恢复到室温后也能够表现出优异的机械物理性质的牙科用光固化性组合物。
本发明的牙科用光固化性组合物包含(A)聚合性单体、(B)光敏剂、(C)光致酸产生剂以及(D)光聚合促进剂,并且(C)光致酸产生剂包含(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。
本发明的牙科用光固化性组合物在从低温恢复到室温后也表现出优异的机械物理性质。
具体实施方式
在本发明中,相对于(A)聚合性单体100质量份,能够包含0.5质量份以上的(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。
在本发明中,作为(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物,能够包含具有含有有机基团以及P、B、Al、S、Ga中的任意一个以上的原子的阴离子的芳基碘鎓盐。
在本发明中,作为(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物,能够包含具有含有至少1个以上的H被F取代的有机基团以及P、B、Al、S、Ga中的任意一个以上的原子的阴离子的芳基碘鎓盐。
在本发明中,作为(D)光聚合促进剂能够包含脂肪族叔胺化合物。
在本发明中,作为(D)光聚合促进剂能够包含(D-1)不具有2个以上的伯羟基的脂肪族叔胺化合物。
在本发明中,其能够是单剂型的牙科用光固化性组合物,相对于(A)聚合性单体100质量份,包含0.005~0.5质量份的(B)光敏剂、0.5~10.0质量份的(C)光致酸产生剂、以及0.01~20质量份的(D)光聚合促进剂。
在本发明中,其能够是双剂型的光固化性组合物,由第一膏和第二膏组成,第一膏与第二膏的比重为1:0.8~1.2,相对于第一膏和第二膏中包含的(A)聚合性单体的合计200质量份,包含0.01~2.0质量份的(B)光敏剂、1.0~20质量份的(C)光致酸产生剂、以及0.02~40质量份的(D)光聚合促进剂。
以下,详细地说明本发明的牙科用光固化性组合物的各成分。本发明的牙科用光固化性组合物作为牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用硬质树脂、牙科切削加工用材料、牙科用3D打印用材料使用。
在牙科临床中,为了对因龋齿或折断等而产生的牙齿的缺失进行审美性和功能性恢复,进行用牙科用复合树脂直接修复或用牙科用树脂水门汀对由陶瓷或牙科用硬质树脂构成的假体装置间接修复的治疗。另外,使用用于将牙科用复合树脂与各种牙科材料和天然牙粘接的牙科用粘接材料、用于固定松动牙的牙科用松动牙固定粘接材料,保护感觉过敏或形成后的活髓牙免受外来刺激或继发龋的牙科用涂布材料,尤其是通过填补乳牙等复杂的沟来预防龋齿的牙科用窝沟裂隙封闭材料,通过遮蔽牙齿变色使审美性暂时恢复的牙科用美容材料,在牙冠部因龋齿而崩坏时用于形成基牙的牙科用基台修筑材料。近年来,新开发了用于通过CAD/CAM加工制作假体装置的牙科切削加工用材料、用于通过3D打印制作假体装置的牙科用3D打印用材料等复合材料,各种牙科材料被用于治疗。对于上述的材料,根据其用途混合由多种聚合性单体构成的树脂基体、无机填料、有机无机复合填料等各种填料以及聚合引发剂,制备成均匀的膏状。举例一部分材料,则是将牙科填充用复合树脂以未固化的膏的状态填充于牙齿,通过仪器等牙科用器具赋予天然牙的解剖学形态后,通过牙科用光照射器等照射光来使其固化从而使用。对于来自光照射器的照射光,通常使用约360~500nm的波长范围内的光强度为100~2000mW/cm2左右的输出光源。另一方面,牙科用树脂水门汀用于将假体装置粘接在窝沟或基牙,在窝沟或基牙上安装假体装置后进行光照射使其固化。
作为用于这种牙科材料的光聚合引发剂,光敏剂和在光敏剂中组合了适当的光聚合促进剂的系统被广泛使用。作为光敏剂,已知酰基氧化膦化合物、α-二酮化合物,特别是α-二酮化合物在对人体影响小的可见光波长区域具有聚合引发能力。另外,作为与光敏剂组合的聚合促进剂,众所周知的是叔胺化合物,α-二酮化合物与叔胺化合物的组合对照射光具有高聚合活性,因此在牙科材料领域中使用。含有该光聚合引发剂的牙科用光固化性组合物表现出各种材料所要求的硬度、弯曲强度、压缩强度等优异的机械特性。
但是,在使用所述α-二酮化合物与叔胺化合物的组合作为光聚合引发剂的情况下,产生环境光稳定性缺乏的问题。即,手术者在像照射口腔内的牙科用灯或者荧光灯那样的室内灯等白色光(环境光)下进行,在仅使用所述α-二酮化合物与叔胺化合物的组合作为光聚合引发剂的情况下,不仅对照射光而且对环境光也表现出高灵敏度,因此,在填充、堆焊、安装等操作中,存在慢慢进行固化、膏的粘度上升、操作变得困难的问题。
为了解决上述问题,提出了包含作为光致酸产生剂的芳基碘鎓盐、增敏剂以及电子供体化合物而成的光聚合引发剂,但在牙科用光固化性组合物中的溶解性上存在问题,由于在低温下保管时析出,因此,在输送到寒冷地区后使用牙科用光固化性组合物时,存在不会表现出充分的物理性质的情况。
本发明人发现了本发明的牙科用光固化性组合物在使用脂溶性高的光致酸产生剂时,在低温保管时不会产生析出,表现出优异的物理性质,从而完成了本发明。更具体地说,发现了芳基碘鎓盐的阴离子的脂溶性对聚合性单体的溶解性产生较大影响。发现了包含与logS(Log Solubility:对数溶解度)为特定值的阴离子形成的芳基碘鎓盐的牙科用光固化性组合物在冷藏、冷冻的保存条件下性状也稳定,logS是通过计算求出的作为与脂溶性相反的特性的水溶性的尺度,从而完成了本发明。
[(A)聚合性单体]
只要本发明的(A)聚合性单体是公知物质,就能够没有限制地使用。在本发明中记载的聚合性单体或具有聚合性基团的化合物中,优选聚合性基团是表现出自由基聚合性的基团,具体而言,从容易自由基聚合的观点出发,聚合性基团优选为(甲基)丙烯酸基和/或(甲基)丙烯酰胺基。需要说明的是,在本说明书中,“(甲基)丙烯酸基”是指丙烯酸基和/或甲基丙烯酸基,“(甲基)丙烯酰基”是指丙烯酰基和/或甲基丙烯酰基,“(甲基)丙烯酸酯”是指丙烯酸酯和/或甲基丙烯酸酯,“(甲基)丙烯酰胺”是指丙烯酰胺和/或甲基丙烯酰胺。还能够优选使用在丙烯酸基和/或丙烯酰胺基的α位上具有取代基的聚合性单体。存在具有一个自由基聚合性基团的化合物,具有两个自由基聚合性基团的化合物,具有三个以上自由基聚合性基团的化合物,具有酸性基团的化合物,具有烷氧基甲硅烷基、硫原子的化合物等。
作为具有一个自由基聚合性基团且不具有酸性基团的聚合性单体的具体例,可举出2-羟乙基(甲基)丙烯酸酯、3-羟丙基(甲基)丙烯酸酯、4-羟丁基(甲基)丙烯酸酯、2-羟丙基(甲基)丙烯酸酯、2-羟丁基(甲基)丙烯酸酯、6-羟己基(甲基)丙烯酸酯、10-羟癸基(甲基)丙烯酸酯、丙二醇单(甲基)丙烯酸酯、丙三醇单(甲基)丙烯酸酯、赤藓醇单(甲基)丙烯酸酯、N-羟甲基(甲基)丙烯酰胺、N-羟乙基(甲基)丙烯酰胺、N,N-(二羟乙基)(甲基)丙烯酰胺、(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸异丙酯、(甲基)丙烯酸丁酯、(甲基)丙烯酸异丁酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸月桂酯、2,3-二溴丙基(甲基)丙烯酸酯、3-(甲基)丙烯酰氧基丙基三甲氧基硅烷、11-(甲基)丙烯酰氧基十一烷基三甲氧基硅烷、(甲基)丙烯酰胺等。
作为具有两个自由基聚合性基团且不具有酸性基团的聚合性单体的具体例,可举出2,2-双((甲基)丙烯酰氧基苯基)丙烷、2,2-双〔4-(3-(甲基)丙烯酰氧基)-2-羟基丙氧基苯基〕丙烷(通称“Bis-GMA”)、2,2-双(4-(甲基)丙烯酰氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基聚乙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基二乙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧四乙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基五乙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基二丙氧基苯基)丙烷、2-(4-(甲基)丙烯酰氧基二乙氧基苯基)-2-(4-(甲基)丙烯酰氧基二乙氧基苯基)丙烷、2-(4-(甲基)丙烯酰氧基二乙氧基苯基)-2-(4-(甲基)丙烯酰氧基二三乙氧基苯基)丙烷、2-(4-(甲基)丙烯酰氧基二丙氧基苯基)-2-(4-(甲基)丙烯酰氧基三乙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基丙氧基苯基)丙烷、2,2-双(4-(甲基)丙烯酰氧基异丙氧基苯基)丙烷、1,4-双(2-(甲基)丙烯酰氧基乙基)均苯四酸酯、丙三醇二(甲基)丙烯酸酯、1-(丙烯酰氧基)-3-(甲基丙烯酰氧基)-2-丙醇、乙二醇二(甲基)丙烯酸酯、二乙二醇二(甲基)丙烯酸酯、三乙二醇二(甲基)丙烯酸酯、丙二醇二(甲基)丙烯酸酯、丁二醇二(甲基)丙烯酸酯、新戊二醇二(甲基)丙烯酸酯、聚乙二醇二(甲基)丙烯酸酯、1,3-丁二醇二(甲基)丙烯酸酯、1,5-戊二醇二(甲基)丙烯酸酯、1,6-己二醇二(甲基)丙烯酸酯、1,10-癸二醇二(甲基)丙烯酸酯、1,2-双(3-甲基丙烯酰氧基-2-羟基丙氧基)乙烷、2,2,4-三甲基六亚甲基双(2-氨基甲酰氧基乙基)二甲基丙烯酸酯(通称“UDMA”)、1,2-双(3-甲基丙烯酰氧基-2-羟基丙氧基)乙烷等。
作为具有三个以上自由基聚合性基团且不具有酸性基团的聚合性单体的具体例,可举出三羟甲基丙烷三(甲基)丙烯酸酯、三羟甲基乙烷三(甲基)丙烯酸酯、三羟甲基甲烷三(甲基)丙烯酸酯、季戊四醇三(甲基)丙烯酸酯、季戊四醇四(甲基)丙烯酸酯、二季戊四醇五(甲基)丙烯酸酯、N,N-(2,2,4-三甲基六亚甲基)双〔2-(氨基羧基)丙烷-1,3-二醇〕四甲基丙烯酸酯、1,7-二丙烯酰氧基-2,2,6,6-四丙烯酰氧基甲基-4-氧基庚烷等。
具有酸性基团的聚合性单体只要是具有一个以上的聚合性基团且至少具有一个以上的磷酸基、焦磷酸基、硫代磷酸基、膦酸基、磺酸基、羧酸基等酸性基团的聚合性单体,就能够没有限制地使用。
作为具有磷酸基的聚合性单体的具体例,可举出2-(甲基)丙烯酰氧基乙基磷酸二氢酯、3-(甲基)丙烯酰氧基丙基磷酸二氢酯、4-(甲基)丙烯酰氧基丁基磷酸二氢酯、5-(甲基)丙烯酰氧基戊基磷酸二氢酯、6-(甲基)丙烯酰氧基己基磷酸二氢酯、7-(甲基)丙烯酰氧基庚基磷酸二氢酯、8-(甲基)丙烯酰氧基辛基磷酸二氢酯、9-(甲基)丙烯酰氧基壬基磷酸二氢酯、10-(甲基)丙烯酰氧基癸基磷酸二氢酯、11-(甲基)丙烯酰氧基十一烷基磷酸二氢酯、12-(甲基)丙烯酰氧基十二烷基磷酸二氢酯、16-(甲基)丙烯酰氧基十六烷基磷酸二氢酯、20-(甲基)丙烯酰氧基二十烷基磷酸二氢酯、双〔2-(甲基)丙烯酰氧基乙基〕磷酸氢酯、双〔4-(甲基)丙烯酰氧基丁基〕磷酸氢酯、双〔6-(甲基)丙烯酰氧基己基〕磷酸氢酯、双〔8-(甲基)丙烯酰氧基辛基〕磷酸氢酯、双〔9-(甲基)丙烯酰氧基壬基〕磷酸氢酯、双〔10-(甲基)丙烯酰氧基癸基〕磷酸氢酯、1,3-二(甲基)丙烯酰氧基丙基磷酸二氢酯、2-(甲基)丙烯酰氧基乙基苯基磷酸氢酯、2-(甲基)丙烯酰氧基乙基-2-溴乙基磷酸氢酯、双〔2-(甲基)丙烯酰氧基-(1-羟甲基)乙基〕磷酸氢酯;这些化合物的酰氯化物、碱金属盐、铵盐;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。
作为具有焦磷酸基的聚合性单体的具体例,可举出焦磷酸双〔2-(甲基)丙烯酰氧基乙酯〕、焦磷酸双〔4-(甲基)丙烯酰氧基丁酯〕、焦磷酸双〔6-(甲基)丙烯酰氧基己酯〕、焦磷酸双〔8-(甲基)丙烯酰氧基辛酯〕、焦磷酸双〔10-(甲基)丙烯酰氧基癸酯〕;这些化合物的酰氯化物、碱金属盐、铵盐;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。
作为具有硫代磷酸基的聚合性单体的具体例,可举出2-(甲基)丙烯酰氧基乙基硫代磷酸二氢酯、3-(甲基)丙烯酰氧基丙基硫代磷酸二氢酯、4-(甲基)丙烯酰氧基丁基硫代磷酸二氢酯、5-(甲基)丙烯酰氧基戊基硫代磷酸二氢酯、6-(甲基)丙烯酰氧基己基硫代磷酸二氢酯、7-(甲基)丙烯酰氧基庚基硫代磷酸二氢酯、8-(甲基)丙烯酰氧基辛基硫代磷酸二氢酯、9-(甲基)丙烯酰氧基壬基硫代磷酸二氢酯、10-(甲基)丙烯酰氧基癸基硫代磷酸二氢酯、11-(甲基)丙烯酰氧基十一烷基硫代磷酸二氢酯、12-(甲基)丙烯酰氧基十二烷基硫代磷酸二氢酯、16-(甲基)丙烯酰氧基十六烷基硫代磷酸二氢酯、20-(甲基)丙烯酰氧基二十烷基硫代磷酸二氢酯;这些化合物的酰氯化物、碱金属盐、铵盐;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。需要说明的是,具有硫代磷酸基的聚合性单体也可以被分类为具有硫原子的聚合性单体。
作为具有膦酸基的聚合性单体的具体例,可举出2-(甲基)丙烯酰氧基乙基苯基膦酸酯、5-(甲基)丙烯酰氧基戊基-3-膦酰基丙酸酯、6-(甲基)丙烯酰氧基己基-3-膦酰基丙酸酯、10-(甲基)丙烯酰氧基癸基-3-膦酰基丙酸酯、6-(甲基)丙烯酰氧基己基-3-膦酰基乙酸酯、10-(甲基)丙烯酰氧基癸基-3-膦酰基乙酸酯;这些化合物的酰氯化物、碱金属盐、铵盐;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。
作为具有磺酸基的聚合性单体的具体例,可举出2-(甲基)丙烯酰胺-2-甲基丙磺酸、2-磺乙基(甲基)丙烯酸酯等。
具有羧酸基的聚合性单体被分类为分子内具有一个羧基的(甲基)丙烯酸系化合物和分子内具有复数个羧基的(甲基)丙烯酸系化合物。作为分子内具有一个羧基的(甲基)丙烯酸系化合物的具体例,可举出(甲基)丙烯酸、N-(甲基)丙烯酰基甘氨酸、N-(甲基)丙烯酰基天冬氨酸、O-(甲基)丙烯酰基酪氨酸、N-(甲基)丙烯酰基酪氨酸、N-(甲基)丙烯酰基苯丙氨酸、N-(甲基)丙烯酰基-对氨基苯甲酸、N-(甲基)丙烯酰基-邻氨基苯甲酸、对乙烯基苯甲酸、2-(甲基)丙烯酰氧基苯甲酸、3-(甲基)丙烯酰氧基苯甲酸、4-(甲基)丙烯酰氧基苯甲酸、N-(甲基)丙烯酰基-5-氨基水杨酸、N-(甲基)丙烯酰基-4-氨基水杨酸、2-(甲基)丙烯酰氧基乙基琥珀酸氢酯、2-(甲基)丙烯酰氧基乙基邻苯二甲酸氢酯、2-(甲基)丙烯酰氧基乙基苹果酸氢酯;这些化合物的酰卤化物;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。作为分子内具有复数个羧基的(甲基)丙烯酸系化合物的具体例,可举出6-(甲基)丙烯酰氧基己烷-1,1-二羧酸、9-(甲基)丙烯酰氧基壬烷-1,1-二羧酸、10-(甲基)丙烯酰氧基癸烷-1,1-二羧酸、11-(甲基)丙烯酰氧基十一烷-1,1-二羧酸、12-(甲基)丙烯酰氧基十二烷-1,1-二羧酸、13-(甲基)丙烯酰氧基十三烷-1,1-二羧酸、4-(甲基)丙烯酰氧基乙基偏苯三酸酯、4-(甲基)丙烯酰氧基丁基偏苯三酸酯、4-(甲基)丙烯酰氧基己基偏苯三酸酯、4-(甲基)丙烯酰氧基癸基偏苯三酸酯、2-(甲基)丙烯酰氧基乙基-3’-(甲基)丙烯酰氧基-2’-(3,4-二羧基苯甲酰氧基)丙基琥珀酸酯;这些化合物的酸酐、酰卤化物;以及这些化合物的酯键被酰胺键取代的(甲基)丙烯酰胺化合物等。
作为具有烷氧基甲硅烷基的聚合性单体的具体例,可举出分子内具有一个烷氧基甲硅烷基的(甲基)丙烯酸系化合物和分子内具有复数个烷氧基甲硅烷基的(甲基)丙烯酸系化合物。可举出2-(甲基)丙烯酰氧基乙基三甲氧基硅烷、3-(甲基)丙烯酰氧基丙基三甲氧基硅烷、3-(甲基)丙烯酰氧基丙基三乙氧基硅烷、3-(甲基)丙烯酰氧基丙基甲基二甲氧基硅烷、4-(甲基)丙烯酰氧基丁基三甲氧基硅烷、5-(甲基)丙烯酰氧基戊基三甲氧基硅烷、6-(甲基)丙烯酰氧基己基三甲氧基硅烷、7-(甲基)丙烯酰氧基庚基三甲氧基硅烷、8-(甲基)丙烯酰氧基辛基三甲氧基硅烷、9-(甲基)丙烯酰氧基壬基三甲氧基硅烷、10-(甲基)丙烯酰氧基癸基三甲氧基硅烷、11-(甲基)丙烯酰氧基十一烷基三甲氧基硅烷。
只要具有硫原子的聚合性单体是具有一个以上的硫原子和聚合性基团的聚合性单体,就能够没有任何限制地使用公知的化合物。具体而言,是指具有-SH、-S-S-、>C=S、>C-S-C<、>P=S等部分结构或通过互变异构产生上述结构的化合物。作为具体例,可举出10-甲基丙烯酰氧基癸基-6,8-二硫代辛酸酯、6-甲基丙烯酰氧基己基-6,8-二硫代辛酸酯、6-甲基丙烯酰氧基己基2-硫尿嘧啶-5-羧酸酯、2-(11-甲基丙烯酰氧基十一烷基硫基)-5-巯基-1,3,4-噻二唑、10-(甲基)丙烯酰氧基癸基硫代磷酸二氢酯。
除这些聚合性单体以外,即使使用分子内具有至少一个以上聚合性基团的低聚物或预聚物也没有任何限制。另外,即使在同一分子内具有氟基等取代基也没有任何问题。以上记载的聚合性单体不仅能够单独使用,还能够组合复数种使用。
本发明的牙科用光固化性组合物能够含有公知的含酸性基团的聚合性单体作为(A)聚合性单体,以赋予对牙质、假体装置的粘接性。优选为10-甲基丙烯酰氧基癸基磷酸二氢酯或6-甲基丙烯酰氧基己基磷酰基乙酸酯。从赋予粘接性的观点出发,相对于牙科用光固化性组合物中所含的聚合性单体的总量100质量份,含酸性基团的聚合性单体的配合量为1质量份以上,更优选为10质量份以上。
本发明的牙科用光固化性组合物中,为了赋予对玻璃陶瓷的粘接性,能够含有硅烷偶联剂作为(A)聚合性单体。只要是公知的硅烷偶联剂,就能够没有限制地使用,但优选3-甲基丙烯酰氧基丙基三甲氧基硅烷、8-甲基丙烯酰氧基辛基三甲氧基硅烷、11-甲基丙烯酰氧基十一烷基三甲氧基硅烷。从赋予粘接性的观点出发,相对于组合物中的聚合性单体的总量100质量份,为1质量份以上,更优选为10质量份以上且小于20质量份的配合量。由于作为聚合性单体的硅烷偶联剂的目的是赋予包含玻璃陶瓷或由玻璃陶瓷构成的填料的树脂材料等粘接性,因此需要与填料的表面处理剂分开配合。
为了赋予对贵金属的粘接性,本发明的牙科用光固化性组合物能够含有具有硫原子的聚合性单体作为(A)聚合性单体。从赋予粘接性的观点出发,相对于牙科用光固化性组合物中所含的聚合性单体100质量份的总量,具有硫原子的聚合性单体的配合量为0.01质量份以上,更优选为0.1质量份以上且小于10质量份的配合量。
<光聚合引发剂>
本发明的牙科用光固化性组合物中使用的光聚合引发剂包含(B)光敏剂、(C)光致酸产生剂以及(D)光聚合促进剂,这些没有特别的限制,通常使用的公知的化合物能够没有任何限制地使用。
[(B)光敏剂]
具体地举例本发明中能够使用的(B)光敏剂,可举出苄基、樟脑醌、樟脑醌羧酸、樟脑醌磺酸、α-萘基、萘乙酮、p,p'-二甲氧基苄基、p,p'-二氯苄基乙酰基、戊二酮、1,2-菲醌、1,4-菲醌、3,4-菲醌、9,10-菲醌、萘醌等α-二酮类、苯偶姻、苯偶姻甲醚、苯偶姻乙醚等苯偶姻烷基醚类;噻吨酮、2-氯噻吨酮、2-甲基噻吨酮、2-异丙基噻吨酮、2-甲氧基噻吨酮、2-羟基噻吨酮、2,4-二乙基噻吨酮、2,4-二异丙基噻吨酮等噻吨酮类;二苯甲酮、对氯二苯甲酮、对甲氧基二苯甲酮等二苯甲酮类;双(2,6-二甲氧基苯甲酰基)苯基氧化膦、双(2,6-二甲氧基苯甲酰基)(2,4,4-三甲基戊基)氧化膦、双(2,6-二甲氧基苯甲酰基)-正丁基氧化膦、双(2,6-二甲氧基苯甲酰基)-(2-甲基丙-1-基)氧化膦、双(2,6-二甲氧基苯甲酰基)-(1-甲基丙-1-基)氧化膦、双(2,6-二甲氧基苯甲酰基)-叔丁基氧化膦、双(2,6-二甲氧基苯甲酰基)环己基氧化膦、双(2,6-二甲氧基苯甲酰基)辛基氧化膦、双(2-甲氧基苯甲酰基)(2-甲基丙-1-基)氧化膦、双(2-甲氧基苯甲酰基)(1-甲基丙-1-基)氧化膦、双(2,6-二乙氧基苯甲酰基)(2-甲基丙-1-基)氧化膦、双(2,6-二乙氧基苯甲酰基)(1-甲基丙-1-基)氧化膦、双(2,6-二丁氧基苯甲酰基)(2-甲基丙-1-基)氧化膦、双(2,4-二甲氧基苯甲酰基)(2-甲基丙-1-基)氧化膦、双(2,4,6-三甲基苯甲酰基)苯基氧化膦、2,4,6-三甲基苯甲酰基二苯基氧化膦、双(2,4,6-三甲基苯甲酰基)(2,4-二戊氧基苯基)氧化膦、双(2,6-二甲氧基苯甲酰基)苄基氧化膦、双(2,6-二甲氧基苯甲酰基)-2-苯基丙基氧化膦、双(2,6-二甲氧基苯甲酰基)-2-苯基乙基氧化膦、双(2,6-二甲氧基苯甲酰基)苄基氧化膦、双(2,6-二甲氧基苯甲酰基)-2-苯基丙基氧化膦、双(2,6-二甲氧基苯甲酰基)-2-苯基乙基氧化膦、2,6-二甲氧基苯甲酰基苄基丁基氧化膦、2,6-二甲氧基苯甲酰基苄基辛基氧化膦、双(2,4,6-三甲基苯甲酰基)异丁基氧化膦和2,6-二甲氧基苯甲酰基-2,4,6-三甲基苯甲酰基-正丁基氧化膦等酰基氧化膦类、双苯甲酰基二乙基锗、双苯甲酰基二甲基锗、双苯甲酰基二丁基锗、双(4-甲氧基苯甲酰基)二甲基锗和双(4-甲氧基苯甲酰基)二乙基锗等酰基锗化合物、2-苄基-二甲基氨基-1-(4-吗啉基苯基)-丁酮-1,2-苄基-二乙基氨基-1-(4-吗啉基苯基)-丙酮-1等α-氨基苯乙酮类、苄基二甲基缩酮、苄基二乙基缩酮、苄基(2-甲氧基乙基缩酮)等缩酮类、双(环戊二烯基)-双〔2,6-二氟-3-(1-吡咯基)苯基〕-钛、双(环戊二烯基)-双(五氟苯基)-钛、双(环戊二烯基)-双(2,3,5,6-四氟-4-二甲硅烷氧基苯基)-钛等茂钛类等。
(B)光敏剂能够根据用于聚合的光的波长、强度、光照射时间、组合的其他成分的种类或配合量来适当选择。另外,光敏剂能够单独使用或组合两种以上使用。其中,优选使用在可见光区域具有最大吸收波长的α-二酮化合物,进一步优选为樟脑醌、樟脑醌羧酸、樟脑醌磺酸等樟脑醌类化合物,特别是,从容易获得的角度出发,优选樟脑醌。
通常,相对于牙科用光固化性组合物中包含的(A)聚合性单体的总量100质量份,(B)光敏剂的配合量优选为0.005~1.0质量份,更优选为0.01~1.0质量份,进一步优选为0.05~1.0质量份。当光敏剂的配合量小于0.005质量份时,缺乏对于照射光的聚合活性,固化不充分。配合大于1.0质量份时,虽然表现出充分的固化性,但是,环境光稳定性变短,黄色调增大。
[(C)光致酸产生剂]
在本发明的牙科用光固化性组合物中,作为(C)光致酸产生剂能够包含(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。在本发明的牙科用光固化性组合物中,能够没有限制地使用(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物与其他公知的光致酸产生剂。具体而言,可举出三嗪化合物、碘鎓盐系化合物、锍盐系化合物、磺酸酯化合物等。其中,由于在与增敏剂联用时聚合性高,因此优选三嗪化合物、碘鎓盐系化合物。更优选为碘鎓盐系化合物。碘鎓盐系化合物容易受到在可见光区域有吸收的光敏剂引发的敏化。
作为三嗪化合物的具体例,可举出2,4,6-三(三氯甲基)-s-三嗪、2,4,6-三(三溴甲基)-s-三嗪、2-甲基-4,6-双(三氯甲基)-s-三嗪、2-甲基-4,6-双(三溴甲基)-s-三嗪、2-苯基-4,6-双(三氯甲基)-s-三嗪、2-(对甲氧基苯基)-4,6-双(三氯甲基)-s-三嗪、2-(对甲基硫代苯基)-4,6-双(三氯甲基)-s-三嗪、2-(对氯苯基)-4,6-双(三氯甲基)-s-三嗪、2-(2,4-二氯苯基)-4,6-双(三氯甲基)-s-三嗪、2-(对溴苯基)-4,6-双(三氯甲基)-s-三嗪、2-(对甲苯基)-4,6-双(三氯甲基)-s-三嗪、2-正丙基-4,6-双(三氯甲基)-s-三嗪、2-(α,α,β-三氯乙基)-4,6-双(三氯甲基)-s-三嗪、2-苯乙烯基-4,6-双(三氯甲基)-s-三嗪、2-[2-(对甲氧基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪、2-[2-(邻甲氧基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪、2-[2-(对丁氧基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪、2-[2-(3,4-二甲氧基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪、2-[2-(3,4,5-三甲氧基苯基)乙烯基]-4,6-双(三氯甲基)-s-三嗪、2-(1-萘基)-4,6-双(三氯甲基)-s-三嗪、2-(4-联苯基)-4,6-双(三氯甲基)-s-三嗪、2-[2-{N,N-双(2-羟乙基)氨基}乙氧基]-4,6-双(三氯甲基)-s-三嗪、2-[2-{N-羟乙基-N-乙基氨基}乙氧基]-4,6-双(三氯甲基)-s-三嗪、2-[2-{N-羟乙基-N-甲基氨基}乙氧基]-4,6-双(三氯甲基)-s-三嗪、2-[2-{N,N-二烯丙基氨基}乙氧基]-4,6-双(三氯甲基)-s-三嗪。其中,优选为2,4,6-三(三氯甲基)-s-三嗪。
对于碘鎓盐系化合物,只要是公知的,就能够使用所有的化合物。作为具体例,碘鎓盐系化合物的结构式能够用下述式(1)表示。
[(R1)2I]+[A]- 式(1)
(式中的[(R1)2I]+是阳离子部分,[A]-是阴离子部分,式(1)所示的R1表示与I键合的有机基团,R1相同或不同。例如,R1表示碳原子数为6~30的芳基、碳原子数为4~30的杂环基、碳原子数为1~30的烷基、碳原子数为2~30的烯基或碳原子数为2~30的炔基,这些基团可以被从烷基、羟基、烷氧基、烷基羰基、芳羰基、烷氧羰基、芳氧羰基、芳硫羰基、酰氧基、芳硫基、烷硫基、芳基、杂环、芳氧基、烷基亚磺酰基、芳基亚磺酰基、烷基磺酰基、芳基磺酰基、亚烷基氧基、氨基、氰基、硝基等各基团和卤素所组成的组中选出的至少一种取代。)
作为上述的碳原子数6~30的芳基,可举出苯基等单环式芳基和萘基、蒽基、菲基、芘基、草屈基(chrysenyl)、并四苯基(naphthacenyl)、苯并蒽基、蒽喹啉基、芴基、萘醌、蒽醌等缩合多环式芳基。
作为碳原子数4~30的杂环基,可举出含1~3个氧、氮、硫等杂原子的环状物质,这些杂原子相同或不同,作为具体例,可举出噻吩基、呋喃基、吡喃基、吡咯基、噁唑基、噻唑基、吡啶基、嘧啶基、吡嗪基等单环式杂环基以及吲哚基、苯并呋喃基、异苯并呋喃基、苯并噻吩基、异苯并噻吩基、喹啉基、异喹啉基、喹喔啉基、喹唑啉基、咔唑基、吖啶基、吩噻嗪基、吩嗪基、呫吨基(Xanthenyl)、噻蒽基(Thianthrenyl)、吩噁嗪基、吩恶噻基、苯并二氢吡喃基(chromanyl)、异苯并二氢吡喃基、二苯并噻吩基、氧杂蒽酮基(xanthonyl)、噻吨酮基(thioxanthonyl)、二苯并呋喃基等缩合多环式杂环基。
作为碳原子数为1~30的烷基的具体例,可举出甲基、乙基、丙基、丁基、十六烷基、十八烷基等直链烷基、异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、异己基等支链烷基;环丙基、环丁基、环戊基、环己基等环烷基。
另外,作为碳原子数为2~30的烯基的具体例,可举出乙烯基、烯丙基、1-丙烯基、异丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-甲基-1-丙烯基等直链或分支状的烯基。
此外,作为碳原子数为2~30的炔基的具体例,可举出乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-1-丙炔基、1-甲基-2-丙炔基等直链或分支状的炔基。
上述碳原子数为6~30的芳基、碳原子数为4~30的杂环基、碳原子数为1~30的烷基、碳原子数为2~30的烯基或碳原子数为2~30的炔基具有或不具有至少一种取代基,作为取代基的具体例,可举出甲基、乙基、丙基、丁基、十八烷基等碳原子数为1~18的直链烷基;异丙基、异丁基、仲丁基、叔丁基等碳原子数为1~18的支链烷基;环丙基、环丁基、环戊基、环己基等碳原子数为3~18的环烷基;羟基;甲氧基、乙氧基、丙氧基、异丙氧基、丁氧基、异丁氧基、仲丁氧基、叔丁氧基、十二烷氧基等碳原子数为1~18的直链或支链的烷氧基;乙酰基、丙酰基、丁酰基、2-甲基丙酰基、庚酰基、2-甲基丁酰基、3-甲基丁酰基、辛酰基等碳原子数为2~18的直链或支链的烷基羰基;苯甲酰基、萘甲酰基等碳原子数为7~11的芳羰基;甲氧羰基、乙氧羰基、丙氧羰基、异丙氧羰基、丁氧羰基、异丁氧羰基、仲丁氧羰基、叔丁氧羰基等碳原子数为2~19的直链或支链的烷氧羰基;苯氧羰基、萘氧羰基等碳原子数为7~11的芳氧羰基;苯硫羰基、萘氧硫羰基等碳原子数为7~11的芳硫羰基;乙酰氧基、乙基羰氧基、丙基羰氧基、异丁基羰氧基、仲丁基羰氧基、叔丁基羰氧基、十八烷基羰氧基等碳原子数为2~19的直链或支链的酰氧基;苯硫基、联苯硫基、甲基苯硫基、氯苯硫基、溴苯硫基、氟苯硫基、羟基苯硫基、甲氧基苯硫基、萘硫基、4-[4-(苯硫基)苯甲酰基]苯硫基、4-[4-(苯硫基)苯氧基]苯硫基、4-[4-(苯硫基)苯基]苯硫基、4-(苯硫基)苯硫基、4-苯甲酰基苯硫基、4-苯甲酰基-氯苯硫基、4-苯甲酰基-甲基硫代苯硫基、4-(甲基硫代苯甲酰基)苯硫基、4-(对叔丁基苯甲酰基)苯硫基等碳原子数为6~20的芳硫基;甲硫基、乙硫基、丙硫基、叔丁硫基、新戊基硫基、十二烷基硫基等碳原子数为1~18的直链或支链的烷硫基;苯基、甲苯基、二甲苯基、萘基等碳原子数为6~10的芳基;噻吩基、呋喃基、吡喃基、呫吨基、苯并二氢吡喃基、异苯并二氢吡喃基、氧杂蒽酮基、噻吨酮基、二苯并呋喃基等碳原子数为4~20的杂环基;苯氧基、萘氧基等碳原子数为6~10的芳氧基;甲基亚磺酰基、乙基亚磺酰基、丙基亚磺酰基、叔戊基亚磺酰基、辛基亚磺酰基等碳原子数为1~18的直链或支链的烷基亚磺酰基;苯基亚磺酰基、甲苯基亚磺酰基、萘基亚磺酰基等碳原子数为6~10的芳基亚磺酰基;甲基磺酰基、乙基磺酰基、丙基磺酰基、异丙基磺酰基、丁基磺酰基、辛基磺酰基等碳原子数为1~18的直链或支链的烷基磺酰基;苯基磺酰基、甲苯基磺酰基(甲苯磺酰基)、萘基磺酰基等碳原子数为6~10的芳基磺酰基;亚烷基氧基;氰基;硝基;氟、氯、溴、碘等卤素等。
在碘鎓盐系化合物中,由于稳定性高,因此优选芳基碘鎓盐。另外,为了提高脂溶性,优选芳基具有取代基。具体而言,优选甲基、丙基、辛基、癸基、十一烷基、十二烷基、十三烷基等直链烷基;异丙基、异丁基、仲丁基、叔丁基、异戊基、新戊基、叔戊基、异己基等支链烷基或这些基团中的一个以上的H被F取代的官能团或全氟烷基、卤素等作为取代基。
对碘鎓盐系化合物阴离子部分的结构没有特别的限定,作为例子,可举出具有卤素、P、S、B、Al、Ga等原子的结构。从安全性的观点出发,能够使用具有As或Sb的阴离子,但在牙科用途中不优选。另外,阴离子优选具有烷基和/或烷氧基和/或芳基等有机基团,此外,最优选具有至少一个以上的H被F取代的烷基和/或烷氧基和/或芳基等有机基团。由于具有这样的阴离子的碘鎓盐系化合物在光固化性组合物中的溶解性高,因此能够期待防止低温保管时或长期保管时的析出、因在短时间内溶解到组合物中而缩短制造时间等。另外,由具有一个以上的H被F取代的烷基和/或烷氧基和/或芳基等有机基团的阴离子构成的碘鎓盐系化合物能够期待更高的溶解性。在光致酸产生剂析出的情况下,由于存在导致光颜色稳定性的降低或弯曲强度的降低的情况,因此不优选。对于这样的具有至少一个以上的H可以被F取代的烷基和/或烷氧基和/或芳基等有机基团的阴离子,能够使用具有任意原子的阴离子,但从通用性和安全性的观点出发,优选具有P、S、B、Al、Ga的物质。
作为不具有烷基和/或烷氧基和/或芳基的阴离子,可举出氯化物、溴化物等卤素或高氯酸等高卤酸、对甲苯磺酸盐等芳香族磺酸、樟脑磺酸、硝酸盐、乙酸盐、氯乙酸盐、羧酸盐、酚盐、四氟硼酸盐、六氟磷酸盐、六氟锑酸盐、六氟砷酸盐等。其中,优选使用对甲苯磺酸盐、樟脑磺酸、羧酸盐。
由于式(1)的碘鎓盐系化合物的[A]-阴离子部分在光聚合组合物中的溶解性提高,因此优选具有至少一个以上的H被F取代的烷基和/或烷氧基和/或芳基等有机基团的阴离子。具体而言,式(1)的碘鎓盐系化合物的[A]-阴离子部分具有的烷基的优选碳原子数为1~8,优选为1~4。作为具体例,可举出甲基、乙基、丙基、丁基、戊基、辛基等直链烷基;异丙基、异丁基、仲丁基、叔丁基等支链烷基;环丙基、环丁基、环戊基、环己基等环烷基等。烷基中的氢原子与氟原子的数量比(F/H)为4以上,烷基中的氢原子与氟原子的数量比(F/H)优选为9以上。进一步优选烃的氢原子全部被氟取代。在光固化性组合物中还可以配合由具有氢原子与氟原子的比率不同的烷基的阴离子构成的碘鎓盐。
此外,作为烷基的具体例,可举出CF3、CF3CF2、(CF3)2CF、CF3CF2CF2、CF3CF2CF2CF2、(CF3)2CFCF2、CF3CF2(CF3)CF、(CF3)3C等直链或支链全氟烷基。
式(1)的碘鎓盐系化合物的[A]-阴离子部分具有的烷氧基的优选碳原子数为1~8,优选为1~4。作为具体例,可举出甲氧基、乙氧基、丙氧基、丁氧基、戊氧基、辛氧基等直链烷氧基或异丙氧基、异丁氧基、仲丁氧基、叔丁氧基等支链烷氧基。烷基中的氢原子与氟原子的数量比(F/H)为4以上,烷基中氢原子与氟原子的数量比(F/H)优选为9以上。进一步优选烃的氢原子全部被氟取代。在光固化性组合物中还可以配合由具有氢原子与氟原子的比率不同的烷氧基的阴离子构成的碘鎓盐。
此外,作为烷氧基的具体例,可举出CF3O、CF3CF2O、CF3CF2CF2O、(CF3)2CFO、CF3CF2CF2CF2O、(CF3)2CFCF2O、CF3CF2(CF3)CFO、CF3CF2CF2CF2CF2O、CF3CF2CF2CF2CF2CF2CF2CF2CF2O等直链或支链全氟烷氧基。
在式(1)的碘鎓盐系化合物的[A]-阴离子部分具有的苯基中具有至少一个以上的氢原子被氟原子、和/或被氟原子取代的烷基和/或烷氧基取代的苯基。被氟原子取代的烷基和/或烷氧基优选上述基团。作为特别优选的苯基的具体例,可举出五氟苯基(C6F5)、三氟苯基(C6H2F3)、四氟苯基(C6HF4)、三氟甲基苯基(CF3C6H4)、双(三氟甲基)苯基((CF3)2C6H3)、五氟乙基苯基(CF3CF2C6H4)、双(五氟乙基)苯基((CF3CF2)2C6H3)、三氟甲基氟苯基(CF3C6H3F)、双三氟甲基氟苯基((CF3)2C6H2F)、五氟乙基氟苯基(CF3CF2C6H3F)、双五氟乙基氟苯基((CF3CF2)2C6H2F)等全氟苯基。在光固化性组合物中还可以配合由具有氢原子与氟原子的比率不同的苯基的阴离子构成的碘鎓盐。
作为式(1)的碘鎓盐系化合物的[A]-阴离子部分的具体例,具有P的阴离子,可举出[(CF3CF2)3PF3]-、[(CF3CF2CF2)3PF3]-、[((CF3)2CF)2PF4]-、[((CF3)2CF)3PF3]-、[((CF3)2CF)4PF2]-、[((CF3)2CFCF2)2PF4]-、[((CF3)2CFCF2)3PF3]-等。具有S的阴离子,可举出[(CF3SO2)3C]-、[(CF3CF2SO2)3C]-、[(CF3CF2CF2SO2)3C]-、[(CF3CF2CF2CF2SO2)3C]-、[CF3CF2CF2CF2SO3]-、[CF3CF2CF2SO3]-、[(CF3CF2SO2)3C]-、[(SO2CF3)3N]-、[(SO2CF2CF3)2N]-、[((CF3)C6H4)SO3]-、[SO3((CF2CF2CF2CF2)SO3]2-等。作为具有B的阴离子,可举出[B(C6F5)4]-、[(C6H5)B(C6F5)3]-、[(C6H5)B((CF3)2C6H3))3]-等。作为具有Ga的阴离子,可举出[((CF3)4Ga)-、[Ga(C6F5)4]-等。作为具有Al的阴离子,可举出[((CF3)3CO)4Al]-、[((CF3CF2)3CO)4Al]-等。
在本发明的牙科用光固化性组合物中,作为(C)光致酸产生剂包含(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。
logS是化合物在水中的溶解性的指标,用于预测化合物的水溶性。在本发明中,使用化学绘图专业软件(ChemDraw Professional ver18.1)进行计算。logS值越大水溶性越高,logS值越小水溶性越低。作为根据这种化合物的结构表现出特性的指标,已知有LogP、CLogP、AlogP、LogD等的分配系数、HSP(汉森溶解度参数)、tPSA(拓扑几何学极性表面积)等。将这些指标与实验结果进行对照,结果确认了上述与溶解性有关的指标和实验结果之间的相关性,其中,基于logS进行了研究,结果发现,通过使用碘鎓盐系化合物,牙科用光固化性组合物在低温保管时的保存稳定性提高。认为通过在牙科用光固化性组合物中配合溶解性高的光致酸产生剂,即使在低温保管时也不会析出,在恢复到室温时也表现出充分的物理性质。并且,还确认了在高温条件下保管时的保存稳定性也优异。这样的碘鎓盐在上述指标中与ClogP有很高的相关性,通常,存在logS的值越大ClogP越低的倾向。以ClogP为指标时,优选与显示1个以上的ClogP的阴离子形成的碘鎓盐。在本发明中,由于在以logS作为指标的情况下能够判断能适用于大量化合物,因此,通过使用logS进行研究,完成了本发明的开发。
举例logS为-4以下的阴离子,可举出[(CF3CF2)3PF3]-、[(CF3CF2CF2)3PF3]-、[((CF3)2CF)2PF4]-、[((CF3)2CF)3PF3]-、[((CF3)2CF)4PF2]-、[((CF3)2CFCF2)2PF4]-、[((CF3)2CFCF2)3PF3]-、[(CF3CF2SO2)3C]-、[(CF3CF2CF2SO2)3C]-、[(CF3CF2CF2CF2SO2)3C]-、[B(C6F5)4]-、[(C6H5)B(C6F5)3]-、[(C6H5)B((CF3)2C6H3))3]-、[((CF3)4Ga]-、[Ga(C6F5)4]-、[((CF3)3CO)4Al]-、[((CF3CF2)3CO)4Al]-等。
另一方面,如果举例logS大于-4的阴离子即脂溶性低的阴离子,可举出氯化物、溴化物、硝酸盐、高氯酸盐、四氟硼酸盐、六氟锑酸盐、六氟磷酸盐、对甲苯磺酸盐、三氟甲烷磺酸盐等。这种阴离子因logS值高而水溶性高,另一方面,因ClogP值低而脂溶性低。例如,上述所示的阴离子的ClogP为1以下。
(C-1)的碘鎓盐系化合物中的阴离子的logS为-4以下,优选为-5以下。如果在牙科用光固化性组合物中相对于(A)聚合性单体的总量100质量份配合0.5质量份以上的与logS大于-4的阴离子形成的碘鎓盐,则在低温条件下保管时有可能析出,特别是,关于溶解性低的阴离子,有时不能均匀地溶解在牙科用光固化性组合物中。在光致酸产生剂不能均匀溶解在牙科用光固化性组合物中的情况下或在光致酸产生剂析出的情况下,有时不能表现出充分的机械特性,光颜色稳定性降低,并且析出的光致酸产生剂被观测为黑点从而影响审美性。
相对于(A)聚合性单体的总量100质量份,优选含有0.5质量份以上的(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物,进一步优选含有1.0质量份以上。小于0.5质量份时,弯曲强度有时不充分,0.5~小于1.0质量份时,存在弯曲强度比含有1.0质量份以上的情况低的倾向。另一方面,相对于(A)聚合性单体的总量100质量份,(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物优选为10质量份以下,进一步优选为5质量份以下。包含大于10质量份时,有时会产生环境光稳定性降低、光颜色稳定性降低等。另外,由于在5~10质量份之间时,不能期待通过增加(C-1)与logS为-4以下阴离子形成的碘鎓盐系化合物的配合量来显著提高弯曲强度,因此,相对于(A)聚合性单体的总量100质量份,配合量最优选为1.0~5.0质量份。(C-1)的碘鎓盐系化合物能够单独使用或组合使用2种以上。
此外,(C)光致酸产生剂并不限于(C-1)的碘鎓盐系化合物,能够组合使用除(C-1)的碘鎓盐系化合物以外的(C)光致酸产生剂。在该情况下,对于本发明的牙科用光固化性组合物,相对于(A)聚合性单体的总量100质量份,包含(C-1)的碘鎓盐系化合物的(C)光致酸产生剂的配合量优选为0.5~10.0质量份。进一步优选为1.0~5.0质量份。配合量小于0.5质量份时,有时会缺乏聚合促进能力,固化不充分。配合大于10质量份时,虽然具有充分的固化性,但有时环境光稳定性变短,固化体带有褐色等变色增大。
本发明的牙科用光固化性组合物,作为(C)光致酸产生剂可以仅包含(C-1)的碘鎓盐系化合物。本发明的牙科用光固化性组合物可以仅包含具有有机基团和P、B、Al、S、Ga中任意一个以上的原子的阴离子与芳基碘鎓阳离子的盐即芳基碘鎓盐。本发明的牙科用光固化性组合物,作为(C)光致酸产生剂可以仅包含具有至少一个以上的H被F取代的有机基团和P、B、Al、S、Ga中任意一个以上的原子的阴离子与芳基碘鎓阳离子的盐。
[(D)光聚合促进剂]
本发明的牙科用光固化性组合物中使用的(D)光聚合促进剂只要是具有聚合促进能力的光聚合促进剂,就没有特别的限制,能够没有任何限制地使用在牙科领域通常使用的公知的光聚合促进剂。作为光聚合促进剂,能够使用芳香族胺化合物、脂肪族胺化合物等伯~叔胺化合物、有机金属化合物、膦化合物等。其中,由于光颜色稳定性优异,因此优选脂肪族叔胺化合物、有机金属化合物。
芳香族胺化合物是指氨(NH3)的1个以上的H取代为芳香环的化合物。能够将NH3的1个H取代为芳香环的化合物分类为芳香族伯胺化合物,将NH3的1个H取代为芳香环且不同的1个H取代为芳香环或烷基的化合物分类为芳香族仲胺化合物,并将NH3的1个H取代为芳香环且不同的2个H取代为芳香环或烷基的化合物分类为芳香族叔胺化合物。
作为芳香族伯胺化合物的具体例,存在苯胺等,作为芳香族仲胺化合物的具体例,存在N-苯基苄胺、N-苄基对茴香胺、N-苄基邻氨基苯乙醚、N-苯基甘氨酸乙酯、N-苯基甘氨酸这样的N保护氨基酸(酯)等,作为芳香族叔胺化合物的具体例,可举出N,N-二甲基苯胺、N,N-二乙基苯胺、N,N-二正丁基苯胺、N,N-二甲基对甲苯胺、N,N-二甲基间甲苯胺、N,N-二乙基对甲苯胺、对溴-N,N-二甲基苯胺、间氯-N,N-二甲基苯胺、对二甲氨基苯甲醛、对二甲氨基苯乙酮、对二甲氨基苯甲酸、对二甲氨基苯甲酸乙酯、对二甲氨基苯甲酸异戊酯、对二甲氨基苯甲酸2-丁氧基乙酯、对二甲氨基苯甲酸2-乙基己酯、对二甲氨基苯甲酸氨基酯、N,N-二甲基邻氨基苯甲酸甲酯、N,N-二羟乙基苯胺、N,N-二羟基乙基对甲苯胺、对二甲氨基苯基醇、对二甲氨基苯乙烯、N,N-二甲基-3,5-二甲基苯胺、4-二甲氨基吡啶、N,N-二甲基-α-萘胺、N,N-二甲基-β-萘胺等。
具体地举例上述有机金属化合物,可举出包含钪(Sc)、钛(Ti)、钒(V)、锰(Mn)、铁(Fe)、钴(Co)、镍(Ni)、铜(Cu)、锡(Sn)、锌(Zn)、锆(Zr)的有机金属化合物,优选为包含锡(Sn)、钒(V)、铜(Cu)的有机金属化合物。作为包含锡(Sn)的有机金属化合物的具体例,可举出二乙酸二丁基锡、二马来酸二丁基锡、二马来酸二辛基锡、二月桂酸二辛基锡、二月桂酸二丁基锡、二叔碳酸二辛基锡、S,S’-双异辛基巯基乙酸二辛基锡、四甲基-1,3-二乙酰氧基二锡氧烷等,作为包含钒(V)的有机金属化合物的具体例,可举出乙酰丙酮钒、四氧化二钒、乙酰丙酮氧钒、硬脂酸氧化钒、草酸钒、硫酸钒、二(1-苯基-1,3-丁二酮)氧代钒、双(麦芽醇)氧钒、五氧化二钒、偏钒酸钠等,作为包含铜(Cu)的有机金属化合物的具体例,可举出乙酰丙酮铜、环烷酸铜、辛酸铜、硬脂酸铜、乙酸铜。
膦化合物是指在P原子上有机基团三取代的化合物,芳香族膦化合物是指在P原子上具有或不具有1个以上的取代基的苯基取代的化合物。作为膦化合物的具体例,可举出三甲基膦、三丁基膦、三己基膦、三正辛基膦、三环己基膦、三(2-噻吩基)膦、二苯丙基膦、二叔丁基(3-甲基-2-丁烯基)膦、甲基二苯基膦、三苯基膦、2-(二苯基膦基)苯乙烯、3-(二苯基膦基)苯乙烯、4-(二苯基膦基)苯乙烯、烯丙基二苯基膦、2-(二苯基膦基)苯甲醛、3-(二苯基膦基)苯甲醛、4-(二苯基膦基)苯甲醛、2-(苯基膦基)苯甲酸、3-(苯基膦基)苯甲酸、4-(苯基膦基)苯甲酸、三(2-甲氧基苯基)膦、三(3-甲氧基苯基)膦、三(4-甲氧基苯基)膦、2-(二苯基膦基)联苯、三(4-氟苯基)膦、三(邻甲苯基)膦、三(间甲苯基)膦、三(对甲苯基)膦、2-(二甲氨基)苯基二苯基膦、3-(二甲氨基)苯基二苯基膦、4-(二甲氨基)苯基二苯基膦、2,2’-双(二苯基膦基)联苯、双[2-(二苯基膦基)苯基]醚等。其中,优选三苯基膦、4-(苯基膦基)苯甲酸、三(邻甲苯基)膦、三(间甲苯基)膦、三(对甲苯基)膦。
脂肪族胺化合物是指氨(NH3)的1个以上的H取代为烷基的化合物。对于烷基,将CH3-或-CH2-分类为伯烷基,将-CH2-的1个H具有取代基的烷基分类为仲烷基,将-CH2-中的2个H具有取代基的烷基分类为叔烷基。对于脂肪族胺,将NH3中的1个H被烷基取代的脂肪族胺分类为脂肪族伯胺化合物,将NH3的2个H被烷基取代的脂肪族胺分类为脂肪族仲胺化合物、将NH3的3个H被烷基取代的脂肪族胺分类为脂肪族叔胺化合物。
作为脂肪族伯胺化合物的具体例,可举出二苯甲胺、三苯基甲胺、甘氨酸等氨基酸或氨基酸酯类等,作为脂肪族仲胺化合物的具体例,可举出二苄胺、N-苄基-1-苯基乙胺、双(1-苯基乙基)胺、双(4-氰基苄基)胺、N-苄基保护氨基酸或N-苄基保护氨基酸酯等,作为脂肪族叔胺化合物的具体例,可举出三丁胺、三丙胺、三乙胺、N,N-二甲基己胺、N,N-二甲基十二胺、N,N-二甲基硬脂胺、N-[3-(二甲氨基)丙基]丙烯酰胺、N,N-二甲基甲酰胺二甲基缩醛、N,N-二甲基乙酰胺二甲基缩醛、N,N-二甲基甲酰胺二乙基缩醛、N,N-二甲基甲酰胺二丙基缩醛、N,N-二甲基甲酰胺二叔丁基缩醛、1-(2-羟乙基)乙烯亚胺、N,N-二甲基乙醇胺、N,N-二甲基异丙醇胺、N,N-二异丙基乙醇胺、N-甲基二乙醇胺、N-乙基二乙醇胺、N-乙基二乙醇胺、N-丁基二乙醇胺、N-月桂基二乙醇胺、N-硬脂基二乙醇胺、三乙醇胺、三苄胺、二苄基甘氨酸乙酯、N’-(2-羟乙基)-N,N,N’-三甲基乙二胺、2-(二甲氨基)-2-甲基-1-丙醇、N,N-二甲基-2,3-二羟基丙胺、N,N-二乙基乙醇胺、1-甲基-3-吡咯烷醇、1-(2-羟乙基)吡咯烷、1-异丙基-3-吡咯烷醇、1-哌啶乙醇、2-[2-(二甲氨基)乙氧基]乙醇、N,N-二甲基甘氨酸、N,N-二甲基甘氨酸甲酯、N,N-二乙基甘氨酸甲酯、N,N-二甲基甘氨酸乙酯、N,N-二乙基甘氨酸钠、乙酸2-(二甲基氨基)乙酯、N-甲基亚氨基二乙酸、N,N-二甲基氨基乙基丙烯酸酯、N,N-二乙基氨基乙基甲基丙烯酸酯、N,N-二丁基氨基乙基甲基丙烯酸酯、N,N-二苄基氨基乙基甲基丙烯酸酯、3-二甲氨基丙腈、三(2-氰乙基)胺、N,N-二甲基烯丙基胺、N,N-二乙基烯丙基胺、三烯丙基胺等。
(D)光聚合促进剂特别优选使用脂肪族叔胺化合物。由于芳香族胺化合物的光颜色稳定性差,因此如果用于像前牙那样的光容易照射的部位的假体装置、修复材料、粘接剂,色调有时会随时间发生变化,因而不优选。另外,通过并用紫外线吸收剂,能够期待抑制光引起的随时间变色。但是,紫外线吸收剂作为通常的添加剂使用,因此不能期待配合带来的机械物理特性的提高,而且,还存在使固化前的牙科用光固化性组合物的黄色调增加的情况,因此不优选大量配合。基于这些原因,优选使用脂肪族叔胺化合物。另外,根据牙科用光固化性组合物的组成不同,在含有脂肪族伯胺化合物和脂肪族仲胺化合物的情况下能够期待高保存稳定性、高机械强度,因此能够没有任何限制地使用公知的物质。
此外,在脂肪族叔胺化合物中,优选分子内不具有2个以上伯羟基的胺化合物,进一步优选分子内不具有伯羟基的胺化合物。作为分子内具有2个以上伯羟基的胺化合物的具体例,可举出三乙醇胺、甲基二乙醇胺等。在长期保管牙科用光固化性组合物的固化体时,具有伯羟基的胺化合物有时会导致变色。分子内的伯羟基的数量越多,变色越有增大的倾向,在分子内具有2个以上的情况下特别显著。能够通过在高温水中条件下保存而在短期内确认长期保管固化体时的变色。在高温水中条件下变色小的情况下,即,在热颜色稳定性高的情况下,长期使用牙科用光固化性组合物的固化体时的变色小。
相对于牙科用光聚合组合物中所含的(A)聚合性单体的总量100质量份,(D)光聚合促进剂优选为0.01~20质量份,进一步优选为0.1~10质量份。小于0.01质量份时,机械强度有时会不充分。配合大于20质量份时,虽然具有充分的固化性,但存在环境光稳定性变短或固化体带有褐色等变色增大的情况,因此不优选。
根据需要,作为聚合引发剂的这些(B)光敏剂、(C)光致酸产生剂、(D)光聚合促进剂实施微粉碎、载体吸附、内包于微胶囊等的二次处理也没有任何问题。进一步,无论聚合方式、聚合方法如何,这些各种光聚合引发剂能够单独使用或组合使用2种以上。
本发明的牙科用光固化性组合物,作为(D)光聚合促进剂也可以仅含有脂肪族叔胺化合物。本发明的牙科用光固化性组合物,作为(D)光聚合促进剂也可以仅含有(D-1)不具有2个以上的伯羟基的脂肪族叔胺化合物。本发明的牙科用光固化性组合物,作为(D)光聚合促进剂也可以仅含有分子内不具有伯羟基的脂肪族叔胺化合物。
[(E)填料]
本发明的牙科用光聚合组合物,作为其他成分能够包含(E)填料。本发明中使用的(E)填料能够没有任何限制地使用通常使用的公知的填料。
作为(E)填料的种类,只要是公知的填料就没有限制,能够根据其用途配合填料,优选配合无机填料、有机填料或有机无机复合填料等填料。这些填料不仅能够单独使用,而且与填料的种类无关地能够组合使用复数种。
作为上述无机填料,对它们的化学组成没有特别的限定,作为具体例,可举出二氧化硅、氧化铝、二氧化硅-二氧化钛、二氧化硅-二氧化钛-氧化钡、二氧化硅-氧化锆、二氧化硅-氧化铝、镧玻璃、硼硅酸玻璃、钠玻璃、钡玻璃、锶玻璃、玻璃陶瓷、铝硅酸盐玻璃、钡硼铝硅酸盐玻璃、锶硼铝硅酸盐玻璃、氟硅酸铝玻璃、钙氟硅酸铝玻璃、锶氟硅酸铝玻璃、钡氟硅酸铝玻璃、锶钙氟硅酸铝玻璃等。特别地,也能够优选使用用于牙科用玻璃离子水门汀、树脂强化型玻璃离子水门汀以及树脂水门汀等的氟铝硅酸钡玻璃、氟铝硅酸锶玻璃、氟铝硅酸玻璃等。此处所述的氟铝硅酸玻璃,以氧化硅和氧化铝为基本骨架,包括用于非交联性氧导入的碱金属。进一步,具有包括锶的作为修饰/配位离子的碱土类金属以及氟。另外,为了进一步赋予X射线不透过性,其为将镧系元素掺入骨架的组合物。该镧系元素根据组成域也作为修饰/配位离子掺入组成。
另外,作为有机填料的具体例,可举出聚甲基丙烯酸甲酯、聚甲基丙烯酸乙酯、甲基丙烯酸甲酯-甲基丙烯酸乙酯共聚体、甲基丙烯酸乙酯-甲基丙烯酸丁酯共聚体、甲基丙烯酸甲酯-三羟甲基丙烷甲基丙烯酸酯共聚体、聚氯乙烯、聚苯乙烯、氯化聚乙烯、尼龙、聚砜、聚醚砜、聚碳酸酯等聚合物。
作为有机无机复合填料,例如,可举出通过聚合性单体将填料的表面聚合包覆而成的复合填料、使填料和聚合性单体混合并聚合后粉碎为适当的粒径而成的复合填料、或者预先使填料分散在聚合性单体从而使其乳化聚合或悬浮聚合的复合填料,但并不受这些复合填料的任何限定。
以提高与聚合性单体的亲和性、在聚合性单体中的分散性、固化体的机械强度以及耐水性为目的,上述(E)填料能够用以硅烷偶联剂为代表的表面处理材料处理。对这种表面处理材料和表面处理方法没有特别限定,能够没有限制地采用公知的方法。作为用于填料的表面处理的硅烷偶联剂,优选甲基三甲氧基硅烷、甲基三乙氧基硅烷、甲基三氯硅烷、二甲基二氯硅烷、三甲基氯硅烷、乙烯基三氯硅烷、乙烯基三乙氧基硅烷、乙烯基三(2-甲氧基乙氧基)硅烷、3-甲基丙烯酰氧基丙基三甲氧基硅烷、3-氯丙基三甲氧基硅烷、3-环氧丙氧基丙基三甲氧基硅烷、3-(甲基)丙烯酰氧基丙基三甲氧基硅烷、8-(甲基)丙烯酰氧基辛基三甲氧基硅烷、11-(甲基)丙烯酰氧基十一烷基三甲氧基硅烷或者六甲基二硅氮烷等。另外,除了硅烷偶联剂以外,还能够通过使用钛酸酯系偶联剂、铝酸酯系偶联剂的方法进行填料的表面处理。相对于处理前的填料100质量份,填料中的表面处理材料的处理量优选为0.01~30质量份,更优选为0.5~20质量份。
对填料的形状没有特别的限定,能够使用不定形、球状、针状、板状、破碎状、鳞片状等任意的形状的填料。另外,填料的平均粒径具有优选为0.2μm~50μm,更优选为0.2μm~30μm,进一步优选为0.2μm~20μm,更进一步优选为0.2μm~10μm的范围的平均粒径。
在牙科用光固化性组合物中配合(E)填料的情况下,相对于(A)聚合性单体的总量100质量份,优选为10~1000质量份,在考虑赋形性等的情况下,优选为小于500质量份。当填充剂的配合量小于10质量份时,存在配合填充剂时的机械强度提高、触变特性的表达效果缺乏的情况,当配合大于1000质量份时,由于组合物的膏性状变硬,有时难以处理,也存在根据填充剂的种类、填充剂的表面处理条件而包含1000质量份以上的情况。例如,该情况是指填充剂为高比重的情况、填充剂中的表面处理剂的量多的情况、或者使用与聚合性单体的亲和性好的表面处理剂的情况等。无论填料的配合量如何,本发明的组合物都表现出效果。
本发明的牙科用光固化性组合物可以包含化学聚合引发剂。作为化学聚合引发剂的有机过氧化物,可举出二酰基过氧化物类、过氧化酯类、二烷基过氧化物类、过氧化缩酮类、酮过氧化物类、过氧化二碳酸酯类、氢过氧化物类。作为二酰基过氧化物类的具体例,可举出乙酰过氧化物、异丁酰过氧化物、苯甲酰过氧化物、癸酰过氧化物、3,5,5-三甲基己酰过氧化物、2,4-二氯苯甲酰过氧化物以及月桂酰过氧化物等。作为过氧化酯类的具体例,可举出α-枯基过氧化新癸酸酯、过氧化新癸酸叔丁酯、过氧化新戊酸叔丁酯、2,2,4-三甲基戊基过氧化-2-乙基己酸酯、叔戊基过氧化-2-乙基己酸酯、叔丁基过氧化-2-乙基己酸酯、二叔丁基过氧化间苯二甲酸酯、二叔丁基过氧六氢对苯二甲酸酯、叔丁基过氧化-3,3,5-三甲基己酸酯、过氧化乙酸叔丁酯、过氧化苯甲酸叔丁酯以及过氧化马来酸叔丁酯等。作为二烷基过氧化物类的具体例,可举出二叔丁基过氧化物、二枯基过氧化物、叔丁基枯基过氧化物、2,5-二甲基-2,5-二(叔丁基过氧化)己烷、1,3-双(叔丁基过氧化异丙基)苯以及2,5-二甲基-2,5-二(叔丁基过氧化)-3-己炔等。作为过氧化缩酮类的具体例,可举出1,1-二(叔丁基过氧化)环己烷、2,2-二(叔丁基过氧化)丁烷、正丁基4,4-(叔丁基过氧化)戊酸酯、1,1-二(叔戊基过氧化)环己烷等。作为酮过氧化物类的具体例,可举出甲乙酮过氧化物、甲基异丁基酮过氧化物、甲基环己酮过氧化物以及环己酮过氧化物等。作为过氧化二碳酸酯类的具体例,可举出二-3-甲氧基过氧化二碳酸酯、二-2-乙基己基过氧化二碳酸酯、双(4-叔丁基环己基)过氧化二碳酸酯、过氧化二碳酸二异丙酯、过氧化二碳酸二正丙酯、过氧化二碳酸二-2-乙氧基乙酯以及过氧化二碳酸二烯丙酯等。作为氢过氧化物类的具体例,可举出2,5-二甲基己烷-2,5-二氢过氧化物、过氧化氢二异丙苯、氢过氧化枯烯、叔丁基氢过氧化物以及1,1,3,3-四甲基丁基氢过氧化物等。
对于有机过氧化物,可以单独使用上述有机过氧化物、或者也可以并用2种以上的有机过氧化物。在这些有机过氧化物中,从固化性的观点出发,优选苯甲酰过氧化物、氢过氧化枯烯。从提高固化性的观点出发,相对于(A)聚合性单体的总量100质量份,作为化学聚合引发剂的有机过氧化物优选设定为0.1~5质量份,进一步优选设定为0.3~3质量份。另外,如果有机过氧化物的配合量多于5质量份,则有时难以充分确保操作时间,另一方面,如果有机过氧化物的配合量小于0.1质量份,则有时机械强度不足。
为了提高固化性,在本发明的牙科用光固化性组合物中还可以配合化学聚合促进剂。作为化学聚合促进剂,可举出第4周期过渡金属化合物、硫脲衍生物、脂肪族胺、芳香族胺、亚磺酸及其盐、硼酸盐化合物、含硫的还原性无机化合物、含氮的还原性无机化合物、巴比妥酸衍生物、三嗪化合物、卤素化合物等。相对于聚合性单体的总量100质量份,化学聚合促进剂的配合量优选为0.01~5质量份,更优选为0.1~3质量份。
作为化学聚合促进剂的第4周期的过渡金属化合物是指周期表第4周期的3~12族的金属化合物,具体而言,只要是钪(Sc)、钛(Ti)、钒(V)、锰(Mn)、铁(Fe)、钴(Co)、镍(Ni)、铜(Cu)、锌(Zn)的各金属化合物,就能够没有限制地使用。此外,上述各过渡金属元素分别可以取复数个价数,但只要是能够稳定存在的价数,就能够添加到本发明的牙科用光固化性组合物中。例如,Sc(3价)、Ti(4价)、V(3、4或5价)、Cr(2、3或6价)、Mn(2~7价)、Fe(2或3价)、Co(2或3价)、Ni(2价)、Cu(1或2价)、Zn(2价)。作为过渡金属化合物的具体例,作为钪化合物,可举出碘化钪(3价)等,作为钛化合物,可举出氯化钛(4价)、四异丙氧基钛(4价)等,作为钒化合物,可举出乙酰丙酮钒(3价)、四氧化二钒(4价)、乙酰丙酮氧钒(4价)、硬脂酸氧化钒(4价)、草酸钒(4价)、硫酸钒(4价)、二(1-苯基-1,3-丁二酮)氧代钒(4价)、双(麦芽醇)氧钒(4价)、五氧化二钒(5价)、偏钒酸钠(5价)等,作为锰化合物,可举出乙酸锰(2价)、环烷酸锰(2价)等,作为铁化合物,可举出乙酸铁(2价)、氯化铁(2价)、乙酸铁(3价)、氯化铁(3价)等,作为钴化合物,可举出乙酸钴(2价)、环烷酸钴(2价)等,作为镍化合物,可举出氯化镍(2价)等,作为铜化合物,可举出氯化铜(1价)、溴化铜(1价)、氯化铜(2价)、乙酸铜(2价)等,作为锌化合物,可举出氯化锌(2价)、乙酸锌(2价)等。
其中,优选3价或4价钒化合物、2价铜化合物,其中,更优选具有更高聚合促进能力的3价或4价钒化合物,最优选为4价钒化合物。这些第4周期的过渡金属化合物根据需要可以并用复数种。相对于(A)聚合性单体的总量100质量份,过渡金属化合物的配合量优选为0.0001~1质量份,小于0.0001质量份时,聚合促进效果有时会不充分,大于1质量份时,导致变色或牙科用光固化性组合物凝胶化,有时贮藏稳定性降低。
作为化学聚合促进剂的硫脲衍生物,只要是公知的硫脲衍生物,就能够没有限制地使用。作为具体例,可举出二甲基硫脲、二乙基硫脲、四甲基硫脲、(2-吡啶基)硫脲、N-甲基硫脲、亚乙基硫脲、N-烯丙基硫脲、N-烯丙基-N’-(2-羟乙基)硫脲、N-苄基硫脲、1,3-二环己基硫脲、N,N'-二苯基硫脲、1,3-二(对甲苯基)硫脲、1-甲基-3-苯基硫脲、N-乙酰硫脲、N-苯甲酰硫脲、二苯基硫脲、二环己基硫脲。其中,优选(2-吡啶基)硫脲、N-乙酰硫脲、N-苯甲酰硫脲。这些硫脲衍生物根据需要可以并用复数种。相对于(A)聚合性单体的总量100质量份,硫脲衍生物的配合量优选为0.1~5质量份,小于0.1质量份时,聚合促进能力有时会不充分,大于5质量份时,有时会降低贮藏稳定性。
作为亚磺酸及其盐,可举出对甲苯亚磺酸、对甲苯亚磺酸钠、对甲苯亚磺酸钾、对甲苯亚磺酸锂、对甲苯亚磺酸钙、苯亚磺酸、苯亚磺酸钠、苯亚磺酸钾、苯亚磺酸锂、苯亚磺酸钙、2,4,6-三甲基苯亚磺酸、2,4,6-三甲基苯亚磺酸钠、2,4,6-三甲基苯亚磺酸钾、2,4,6-三甲基苯亚磺酸锂、2,4,6-三甲基苯亚磺酸钙、2,4,6-三乙基苯亚磺酸、2,4,6-三乙基苯亚磺酸钠、2,4,6-三乙基苯亚磺酸钾、2,4,6-三乙基苯亚磺酸锂、2,4,6-三乙基苯亚磺酸钙、2,4,6-三异丙基苯亚磺酸、2,4,6-三异丙基苯亚磺酸钠、2,4,6-三异丙基苯亚磺酸钾、2,4,6-三异丙基苯亚磺酸锂、2,4,6-三异丙基苯亚磺酸钙等,特别优选苯亚磺酸钠、对甲苯亚磺酸钠、2,4,6-三异丙基苯亚磺酸钠。
作为硼酸盐化合物,作为1分子中具有1个芳基的硼酸盐化合物的具体例,可举出三烷基苯基硼、三烷基(对氯苯基)硼、三烷基(对氟苯基)硼、三烷基(3,5-双三氟甲基)苯基硼、三烷基[3,5-双(1,1,1,3,3,3-六氟-2-甲氧基-2-丙基)苯基]硼、三烷基(对硝基苯基)硼、三烷基(间硝基苯基)硼、三烷基(对丁基苯基)硼、三烷基(间丁基苯基)硼、三烷基(对丁氧基苯基)硼、三烷基(间丁氧基苯基)硼、三烷基(对辛氧基苯基)硼和三烷基(间辛氧基苯基)硼(烷基是从由正丁基、正辛基以及正十二烷基等所组成的组中选出的至少一种)的钠盐、锂盐、钾盐、镁盐、四丁基铵盐、四甲基铵盐、四乙基铵盐、甲基吡啶鎓盐、乙基吡啶鎓盐、丁基吡啶鎓盐、甲基喹啉鎓盐、乙基喹啉鎓盐、丁基喹啉鎓盐等。作为1分子中具有2个芳基的硼酸盐化合物的具体例,可举出二烷基二苯基硼、二烷基二(对氯苯基)硼、二烷基二(对氟苯基)硼、二烷基二(3,5-双三氟甲基)苯基硼、二烷基二[3,5-双(1,1,1,3,3,3-六氟-2-甲氧基-2-丙基)苯基]硼、二烷基二(对硝基苯基)硼、二烷基二(间硝基苯基)硼、二烷基二(对丁基苯基)硼、二烷基二(间丁基苯基)硼、二烷基二(对丁氧基苯基)硼、二烷基二(间丁氧基苯基)硼、二烷基二(对辛氧基苯基)硼以及二烷基二(间辛氧基苯基)硼(烷基是从由正丁基、正辛基以及正十二烷基等所组成的中选出的至少一种)的钠盐、锂盐、钾盐、镁盐、四丁基铵盐、四甲基铵盐、四乙基铵盐、甲基吡啶鎓盐、乙基吡啶鎓盐、丁基吡啶鎓盐、甲基喹啉鎓盐、乙基喹啉鎓盐以及丁基喹啉鎓盐等。作为1分子中具有3个芳基的硼酸盐化合物的具体例,可举出单烷基三苯基硼、单烷基三(对氯苯基)硼、单烷基三(对氟苯基)硼、单烷基三(3,5-双三氟甲基)苯基硼、单烷基三[3,5-双(1,1,1,3,3,3-六氟-2-甲氧基-2-丙基)苯基]硼、单烷基三(对硝基苯基)硼、单烷基三(间硝基苯基)硼、单烷基三(对丁基苯基)硼、单烷基三(间丁基苯基)硼、单烷基三(对丁氧基苯基)硼、单烷基三(间丁氧基苯基)硼、单烷基三(对辛氧基苯基)硼以及单烷基三(间辛氧基苯基)硼(烷基是从正丁基、正辛基或正十二烷基等选出的1种)的钠盐、锂盐、钾盐、镁盐、四丁基铵盐、四甲基铵盐、四乙基铵盐、甲基吡啶鎓盐、乙基吡啶鎓盐、丁基吡啶鎓盐、甲基喹啉鎓盐、乙基喹啉鎓盐、丁基喹啉鎓盐等。具体地举出1分子中具有4个芳基的硼酸盐化合物,例如,可举出四苯基硼、四(对氯苯基)硼、四(对氟苯基)硼、四(3,5-双三氟甲基)苯基硼、四[3,5-双(1,1,1,3,3,3-六氟-2-甲氧基-2-丙基)苯基]硼、四(对硝基苯基)硼、四(间硝基苯基)硼、四(对丁基苯基)硼、四(间丁基苯基)硼、四(对丁氧基苯基)硼、四(间丁氧基苯基)硼、四(对辛氧基苯基)硼、四(间辛氧基苯基)硼、(对氟苯基)三苯基硼、(3,5-双三氟甲基)苯基三苯基硼、(对硝基苯基)三苯基硼、(间丁氧基苯基)三苯基硼、(对丁氧基苯基)三苯基硼、(间辛氧基苯基)三苯基硼以及(对辛氧基苯基)三苯基硼的钠盐、锂盐、钾盐、镁盐、四丁基铵盐、四甲基铵盐、四乙基铵盐、甲基吡啶鎓盐、乙基吡啶鎓盐、丁基吡啶鎓盐、甲基喹啉鎓盐、乙基喹啉鎓盐以及丁基喹啉鎓盐等。
在这些芳基硼酸盐化合物中,从保存稳定性的观点出发,更优选使用1分子中具有3个或4个芳基的硼酸盐化合物。另外,这些芳基硼酸盐化合物也能够使用1种或混合使用2种以上。
作为含硫的还原性无机化合物,可举出亚硫酸盐、亚硫酸氢盐、焦亚硫酸盐、硫代硫酸盐、硫磺酸盐(thionate)、连二亚硫酸盐等,作为具体例,可举出亚硫酸钠、亚硫酸钾、亚硫酸钙、亚硫酸铵、亚硫酸氢钠、亚硫酸氢钾、3-巯基丙基三甲氧基硅烷、2-巯基苯并恶唑、癸硫醇、硫代苯甲酸等。
作为含氮的还原性无机化合物,可举出亚硝酸盐,作为具体例,可举出亚硝酸钠、亚硝酸钾、亚硝酸钙、亚硝酸铵等。
作为巴比妥酸衍生物,可举出巴比妥酸、1,3-二甲基巴比妥酸、1,3-二苯基巴比妥酸、1,5-二甲基巴比妥酸、5-丁基巴比妥酸、5-乙基巴比妥酸、5-异丙基巴比妥酸、5-环己基巴比妥酸、1,3,5-三甲基巴比妥酸、1,3-二甲基-5-乙基巴比妥酸、1,3-二甲基-正丁基巴比妥酸、1,3-二甲基-5-异丁基巴比妥酸、1,3-二甲基巴比妥酸、1,3-二甲基-5-环戊基巴比妥酸、1,3-二甲基-5-环己基巴比妥酸、1,3-二甲基-5-苯基巴比妥酸、1-环己基-1-乙基巴比妥酸、1-苄基-5-苯基巴比妥酸、5-甲基巴比妥酸、5-丙基巴比妥酸、1,5-二乙基巴比妥酸、1-乙基-5-甲基巴比妥酸、1-乙基-5-异丁基巴比妥酸、1,3-二乙基-5-丁基巴比妥酸、1-环己基-5-甲基巴比妥酸、1-环己基-5-乙基巴比妥酸、1-环己基-5-辛基巴比妥酸、1-环己基-5-己基巴比妥酸、5-丁基-1-环己基巴比妥酸、1-苄基-5-苯基巴比妥酸和硫代巴比妥酸类的盐(优选为碱金属或碱土类金属类),作为这些巴比妥酸类的盐的具体例,可举出5-丁基巴比妥酸钠、1,3,5-三甲基巴比妥酸钠和1-环己基-5-乙基巴比妥酸钠等。
作为卤素化合物的具体例,可举出二月桂基二甲基氯化铵、月桂基二甲基苄基氯化铵、苄基三甲基氯化铵、四甲基氯化铵、苄基二甲基鲸蜡基氯化铵、二月桂基二甲基溴化铵等。
本发明的牙科用光固化性组合物能够不含有化学聚合引发剂和化学聚合促进剂。本发明的牙科用光固化性组合物能够不含除光聚合体系以外的聚合体系的聚合引发剂体系。
<其他的成分>
另外,只要在不抑制本发明的效果的范围内,在本发明的牙科用光固化性组合物中可以包含除上述(A)~(D)的成分以外的成分。例如,能够根据需要任意地添加二苯甲酮系、苯并三唑系的紫外线吸收剂、对苯二酚、对苯二酚单甲醚、2、5-二叔丁基-4-甲基苯酚等阻聚剂;α-烷基苯乙烯化合物、正丁基硫醇、正辛基硫醇等硫醇化合物;柠檬烯、月桂烯、α-松油烯、β-松油烯、γ-松油烯、异松油烯、β-蒎烯、α-蒎烯等类萜系化合物等链转移剂;氨基羧酸系螯合剂、膦酸系螯合剂等金属捕捉材;变色抑制剂、抗菌剂、着色颜料、水以及能够与水以任意的比率混和的溶剂、其他的以往公知的添加剂等成分。
对制备本发明的牙科用光固化性组合物的方法没有特别限制。作为牙科用光固化性组合物的一般制造方法,例如在牙科用光固化性组合物包含(E)的情况下,可举出制备预先将(A)聚合性单体、(B)光敏剂、(C)光致酸产生剂和(D)光聚合促进剂混合而成的基体后,将该基体和(E)填料混炼,在真空下去除气泡从而制备成均匀膏状的方法。在本发明中,也能够通过上述的制造方法没有任何问题地制造。
本发明的牙科用光固化性组合物用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用硬质树脂、牙科切削加工用材料、牙科用3D打印用材料等。
<单剂型牙科用光固化性组合物>
将本发明用于单剂型牙科用光固化性组合物中使用时,特别是,优选作为牙科材料用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用硬质树脂、牙科切削加工用材料、牙科用3D打印用材料,特别优选用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用硬质树脂。当其为单剂型的牙科用光固化性组合物时,能够期待技术错误少,气泡的混入风险少。
<双剂型牙科用光固化性组合物>
将本发明用于双剂型牙科用光固化性组合物时,特别是,优选作为牙科材料用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用硬质树脂、牙科切削加工用材料、牙科用3D打印用材料,特别优选用于牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀。双剂型牙科材料通过在即将使用分为第一膏和第二膏的双剂前捏合来使用。捏合以第一膏和第二膏为0.9~1.1:1.0的体积比或0.8~1.2:1.0的质量比、优选为等体积比进行。捏合的方法能够通过使用专用的振荡装置、刮刀等的手动捏合、通过静态搅拌器的自动捏合等公知的方法进行。由于能够将成分分为双剂,能够将不能配合在同一膏中的化合物分开配合,因此贮藏稳定性优异。
本发明的牙科用光固化性组合物包含(A)聚合性单体、(B)光敏剂、(C)光致酸产生剂以及(D)光聚合促进剂,(C)光致酸产生剂也可以仅包含(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。另外,作为除(A)~(D)以外的成分,可以仅包含上述成分中的1种以上。
[实施例]
下面,具体地说明本发明的实施例,本发明并不限定于这些实施例。
实施例以及比较例中使用的材料及其简称如下所示。
[(A)聚合性单体]
Bis-GMA:2,2-双〔4-(3-甲基丙烯酰氧基)-2-羟基丙氧基)苯基〕丙烷。
2.6E:乙氧基的平均加成摩尔数为2.6的2,2-双(4-(甲基)丙烯酰氧基聚乙氧基苯基)丙烷。
UDMA:N,N-(2,2,4-三甲基六亚甲基)双[2-(氨基羧基)乙醇]甲基丙烯酸酯。
TEGDMA:三乙二醇二甲基丙烯酸酯。
NPG:新戊二醇二甲基丙烯酸酯。
HEMA:2-羟乙基甲基丙烯酸酯。
MDP:10-甲基丙烯酰氧基癸基磷酸二氢酯。
MHPA:6-甲基丙烯酰氧基己基膦酰基乙酸酯。
[(B)光敏剂]
CQ:樟脑醌。
BAPO:苯基双(2,4,6-三甲基苯甲酰基)氧化膦。
[(D)光聚合促进剂]
<脂肪族叔胺>
<<不具有伯羟基的脂肪族叔胺化合物>>
TBA:三苄胺。
DBGE:N,N-二苄基甘氨酸乙酯。
DEAEMA:N,N-二乙基氨基乙基甲基丙烯酸酯。
DMAEMA:N,N-二甲氨基乙基甲基丙烯酸酯。
<<具有1个伯羟基的脂肪族叔胺化合物>>
DBAE:N,N-二苄基氨基乙醇。
<<具有2个伯羟基的脂肪族叔胺化合物>>
MDEOA:甲基二乙醇胺。
<<具有3个伯羟基的脂肪族叔胺化合物>>
TEA:三乙醇胺。
<芳香族叔胺化合物>
DMBE:N,N-二甲氨基苯甲酸乙酯。
<有机金属化合物>
DBTL:二月桂酸二丁基锡。
[(E)填料]
以下示出用于制备光固化性组合物的各填料的制造方法。
(填料1)
在硅酸锆填料(平均粒径1.2μm:氧化锆90wt%,二氧化硅10wt%)100.0g中添加硅烷偶联处理液,并搅拌混合30分钟,该硅烷偶联处理液是通过将水50.0g、乙醇35.0g、作为硅烷偶联剂的8-甲基丙烯酰氧基辛基三甲氧基硅烷7.0g在室温条件下搅拌2小时而获得的。接着,以140℃实施15小时的热处理,得到填料1。
(填料2)
在硅酸锆填料(平均粒径0.8μm,氧化锆85wt%,二氧化硅15wt%)100.0g中添加硅烷偶联处理液,并搅拌混合30分钟,该硅烷偶联处理液是通过将水50.0g、乙醇35.0g、作为硅烷偶联剂的3-甲基丙烯酰氧基丙基三甲氧基硅烷7.0g在室温条件下搅拌2小时而获得的。接着,以140℃实施15小时的热处理,得到填料2。
[化学聚合引发剂]
CHP:氢过氧化枯烯。
BPO:过氧化苯甲酰。
TPE:1,1,3,3-四甲基丁基过氧化-2-乙基己酸酯。
[化学聚合促进剂]
PTU:(2-吡啶基)硫脲。
DEPT:N,N-二羟乙基对甲苯胺。
DMPT:N,N-二甲基对甲苯胺。
COA:乙酰丙酮铜。
VOA:乙酰丙酮氧钒。
[紫外线吸收剂]
BT:2-(2-羟基-5-甲基苯基)苯并三唑。
[阻聚剂]
·BHT:2,6-二叔丁基-4-甲基苯酚。
·MeHQ:对甲氧基苯酚。
[荧光剂]
FA:2,5-二羟基对苯二甲酸二乙酯。
[(C)光致酸产生剂]
碘鎓盐阴离子的氢化物的logS使用化学绘图专业软件(ChemDraw Professionalver18.1)进行计算。
<(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物>
C1:双[4-(叔丁基)苯基]碘鎓四(五氟苯基)镓酸盐(LogS:-15.1)。
C2:二对甲苯基碘鎓苯基三(五氟苯基)硼酸盐(LogS:-11.3)。
C3:双(4-叔丁基苯基)碘鎓四(九氟-叔丁氧基)铝酸盐(LogS:-14.7)。
C4:对枯烯基(对甲苯基)碘鎓三(五氟乙烷磺酰基)甲基化物(LogS:-5.3)。
C5:二苯基碘鎓三(九氟丁烷磺酰基)甲基化物(LogS:-9.4)。
C6:双(4-叔丁基苯基)碘鎓三(五氟丙基)三氟磷酸盐(ClogP:-5.2)。
C7:对枯烯基(对甲苯基)碘鎓三(五氟乙基)三氟磷酸盐(ClogP:-7.2)。
C8:对枯烯基(对甲苯基)碘鎓双(三氟甲基)四氟磷酸盐(ClogP:-4.7)。
C9:对枯烯基(对甲苯基)碘鎓(三氟甲基)五氟磷酸盐(ClogP:-4.1)。
<包含logS大于-4的阴离子的光致酸产生剂>
C11:双(4-叔丁基苯基)碘鎓-对甲苯磺酸盐(LogS:-2.1)。
C12:二苯基碘鎓三氟甲磺酸盐(LogS:-0.7)。
C13:氯代二苯碘鎓盐(LogS:0.2)。
C14:双(4-叔丁基苯基)碘鎓六氟磷酸盐。
<单剂型牙科用光固化性组合物的制造方法>
将表1所示的除(E)填料以外的全部成分投入到广口塑料容器中,使用混合转子VMRC-5在100rpm的条件下混合48小时,得到基体。然后,将基体和(E)填料投入混炼机,均匀搅拌后,在真空下脱泡制备牙科用光固化性组合物。需要说明的是,在表1中,在各成分的缩写之后对各成分的质量份加上括号来记载。
表1
<双剂型牙科用光固化性组合物的制造方法>
将表2所示的除(E)填料以外的全部成分投入到广口塑料容器中,使用混合转子VMRC-5在100rpm的条件下混合48小时,得到基体。然后,将基体和(E)填料投入混炼机,均匀搅拌后,在真空下脱泡得到膏1、2后,向混合包装公司(ミックスパック社)制的双注射器(5mL)中填充膏1、2,制备牙科用光固化性组合物。对于双剂型牙科用光固化性组合物,使用用混合包装公司制的搅拌头(mixing tip)将膏1和2混合而成的膏。混合包装公司制的搅拌头为静态搅拌器,使用它时,膏1和膏2能够以0.9~1.1:1.0的体积比捏合,换算成质量比时,膏1和膏2捏合成0.8~1.2:1.0来使用。需要说明的是,在表2中,在各成分的缩写之后对各成分的质量份加上括号来记载。
表2
<加速试验条件>
将填充在各容器中的单剂型牙科用光固化性组合物和双剂型牙科用光固化性组合物静置在设定为40℃的保管库(大和科学株式会社(ヤマト科学株式会社))和设定为-5℃的保管库(KGT-4010HC,日本弗利兹株式会社(日本フリーザー株式会社))中,保管6个月。
<评价1:外观的确认>
从保管库中取出在-5℃条件下保管的单剂型牙科用光固化性组合物和双剂型牙科用光固化性组合物后,在15~25℃的常温条件下静置1周,从容器排出1g的膏,此时,将目视未确认到析出物的情况判定为A:良好;将确认了1个以上且5个以下的析出物的情况判断为B:在允许范围内;将确认了5个以上的情况判断为C:外观有问题。
<评价2:通过弯曲强度确认保存稳定性>
将牙科用光固化性组合物填充到不锈钢制模具中后,在两面放置盖玻片,用玻璃混合板压接后,使用光聚合照射器(pen bright:松风制)在5个部位各进行10秒钟光照射,使其固化。固化后,从模具中取出固化物后,再次同样地对背面也进行光照射,将其作为试验样品(25×2×2mm:长方体型)。将该试验样品在37℃水中浸渍24小时后,进行弯曲试验。对于双剂型光固化性组合物,在进行光照射后1小时内实施弯曲试验。弯曲试验使用英斯特朗万能试验机(英斯特朗公司(インストロン社)制),在支点间距离20mm、十字头速度1mm/min的条件下进行。使用(式2)通过弯曲试验的结果进行保存稳定性的评价。如果与保管前相比变化大于-5%以上,则具有高保存稳定稳定性。如果变化在-5%~-15%之间,则保存稳定性略差。如果其是低于-15%的值,则判断保存稳定性显著差。
(保管后的弯曲强度(MPa)-保管前的弯曲强度(MPa))/(保管前的弯曲强度(MPa))×100[%](式2)
进一步,另外进行加速试验前的弯曲强度的评价。对于相对于聚合性单体100质量份含有100质量份以上的(E)填料的单剂型光固化性组合物和双剂型光固化性组合物的弯曲强度,将大于100MPa判断为良好,将其80~100MPa判断为能够适用,当弯曲强度小于80MPa时判断为不充分。对于相对于聚合性单体100质量份含有小于100质量份的(E)填料的单剂型光固化性组合物和双剂型光固化性组合物的弯曲强度,将大于90MPa判断为良好,将60~90MPa判断为能够适用,将小于60MPa时判断为不充分。弯曲强度根据填充剂的配合量不同而不同,因此设定了不同的基准。
<评价3:环境光稳定性>
使用光度计调节牙科用灯(Luna-Vue S,森田制作所(モリタ制作所)制)的高度,使得照度8000±1000lx的光照射到试样设置部。在铺有无光泽的黑色纸的玻璃混合板上放置载玻片(26×16mm,厚2mm)后,在其上采取约30mg的试样。在试样设置部使试样曝光60±5秒后,从试样设置部取出试样,立即将其他载玻片压在试样上,形成薄层。如果此时的试样状态没有保持物理上均匀的状态,则判定为固化开始,以5秒为单位评价到固化为止的时间。该时间越长,环境光稳定性越优异。对于环境光稳定性,将90秒以上判断为良好,将60秒以上~小于90秒判断为能够适用,将小于60秒判断为不充分。环境光稳定性表示从容器中排出牙科用光固化性组合物,在直至适应为止的时间内不会因荧光灯等环境光而固化,能够充分改变形状的时间。由于口腔内空间狭小,操作不方便,且每个人的天然牙的形状都很复杂,因此,为了适应各种病例,环境光稳定性越长越优选。
<评价4:光颜色稳定性>
将制备的牙科用光固化性组合物分别充满不锈钢制模具(15φ×1mm:圆盘状)后,从上部放置盖玻片并用玻璃板进行压接。用光聚合照射器(Griplight II:松风制)从盖玻片上进行1分钟的光照射使其固化,从模具取出固化物后,取下盖玻片,测量该试验样品的色调。将试验样品放置在标准白色板(D65/10°X=81.07,Y=86.15,Z=93.38)的背景上,使用分光色度计(毕克化学公司(ビックケミー社)制)在规定的一定条件下(光源:C,视角:2°,测定面积:11mm)进行测色。接着,通过疝灯光暴露试验机(Suntest CPS+)使试验样品光暴露24小时后,再次测定试验样品的色调,其变色的差异用通过下述式计算出的ΔE表示。
ΔE={(ΔL*)2+(Δa*)2+(Δb*)2}1/2
ΔL*=L1*-L2*
Δa*=a1*-a2*
Δb*=b1*-b2*
其中,L1*为光暴露前的亮度指数,L2*为光暴露后的亮度指数,a1、b1*为光暴露前的色质指数,a2*、b2*为光暴露后的色质指数。将ΔE小于5的情况判断为最好,将ΔE为5~10的情况判断为良好,将ΔE大于10的情况判断为能够适用。在光颜色稳定性良好的情况下,在使用时变色少且能够维持高审美性。
<评价5:热颜色稳定性>
将制备的牙科用光固化性组合物分别充满不锈钢制模具(15φ×1mm:圆盘状)后,从上部放置盖玻片并用玻璃板进行压接。用光聚合照射器(Griplight II:松风制)从盖玻片上进行1分钟的光照射使其固化,从模具中取出固化物后,取下盖玻片,测量该试验样品的色调。将试验样品放置在标准白色板(D65/10°X=81.07,Y=86.15,Z=93.38)的背景上,使用分光色度计(毕克化学公司(ビックケミー社)制)在规定的一定条件下(光源:C,视角:2°,测定面积:11mm)进行测色。然后,在设定为70℃的恒温器中,将试验样品浸渍在装有10mL水的容器中后,静置一周后,再次测定试验样品的色调,其变色的差异用通过下述式计算出的ΔE表示。
ΔE={(ΔL*)2+(Δa*)2+(Δb*)2}1/2
ΔL*=L1*-L2*
Δa*=a1*-a2*
Δb*=b1*-b2*
其中,L1*为浸渍/静置前的亮度指数,L2*为浸渍/静置后的亮度指数,a1、b1*为浸渍/静置前的色质指数,a2*、b2*为浸渍/静置后的色质指数。A,将ΔE小于5的情况判断为最好;将ΔE为5~10的情况判断为良好;将ΔE大于10的情况判断为能够适用。在热稳定性良好的情况下,在口腔内长期使用牙科材料时变色少,能够长期维持高审美状态。
对表3和表4所示的各试验的结果进行描述。
表3
表4
确认了实施例中记载的组合物在制备阶段表现出80MPa以上的弯曲强度,并且即使在低温条件下长期保管的情况下,弯曲强度也不会大幅降低。
对于实施例A8、A9、A15、A16、A23、B8、B9、B15、B16、B17,由于光致酸产生剂的配合量略少,弯曲强度显示出略低的值。另一方面,确认了像实施例A12、A13、A14、B14那样在光致酸产生剂的配合量略多的情况下,在进行40℃的高温下的保管试验时,弯曲强度存在降低的倾向,环境光稳定性变短、光颜色稳定性降低等。光致酸产生剂含有logS为-4~-5的阴离子和碘鎓阳离子的盐即碘鎓盐化合物的C8、C9时,像实施例A8、A9、B8、B9那样配合量少的情况下,低温保管也没有问题,配合量增加的实施例A10、A11、B10、B11、进一步增加的实施例A12、A13、B12、B13的保存稳定性存在略微降低的倾向,低温保管时确认了一些析出物,存在光颜色稳定性略差的倾向,但是其为在能够没有问题地使用的范围内的变化。另外,确认了像实施例A16、A17那样,即使包含logS大于-4的阴离子和碘鎓阳离子的盐即碘鎓盐化合物,如果是相对于聚合性单体100质量份为0.1质量份左右的微量,也不会对保存稳定性产生很大影响。
确认了实施例A22、B22因光敏剂的配合量略少而存在弯曲强度降低的倾向,实施例A21、A47、B21虽然因光敏剂的配合量略多而弯曲强度高,但是存在环境光稳定性降低、光颜色稳定性降低的倾向。另外,与光敏剂含有α-二酮类化合物的组合物相比,光敏剂含有酰基氧化膦即BAPO的实施例A36、B36存在弯曲强度降低的倾向。
确认了实施例A18、A48、B18因光聚合促进剂的配合量略少而存在弯曲强度低的倾向,实施例A19、A20、B20虽然因光聚合促进剂的配合量略多而弯曲强度高,但是存在环境光稳定性降低、光颜色稳定性降低的倾向。
实施例A26、A27、B26、B27含有具有1个伯羟基的二苄基氨基乙醇(DBAE)作为光聚合促进剂,实施例A28、B28含有具有2个伯羟基的甲基二乙醇胺作为光聚合促进剂,实施例A29、B29含有具有3个伯羟基的三乙醇胺作为光聚合促进剂。将它们进行比较,确认了随着伯羟基的数量增加,存在热颜色稳定性降低的倾向,特别是通过具有2个以上的伯羟基,热颜色稳定性大幅降低。
实施例A30、A31、A32、B30、B31、B32含有作为芳香族胺的DMBE作为光聚合促进剂。确认了在含有芳香族胺的情况下,光颜色稳定性降低。另一方面,像实施例A33、A34、B33、B34那样在包含芳香族胺以及紫外线吸收剂的组合物的情况下,能够防止光颜色稳定性降低。但是,由于紫外线吸收剂使固化体的黄色升高,其本身无助于提高物理性质,因此有时会因大量配合而引起机械强度降低,因此更优选不配合。
实施例B41、B42、B44、B45含有芳香族胺作为化学聚合促进剂,与含有芳香族胺作为光聚合促进剂同样地,光颜色稳定性存在降低的趋势。另外,含有DEPT这样的分子内具有2个伯羟基的芳香族胺的实施例B42、B44、B45的热颜色稳定性也存在降低的趋势。
比较例CA1、CB1因不含光敏剂而不固化、或者弯曲强度显著降低。比较例CA2、CB3由于不含光致酸产生剂,因此弯曲强度显著降低。比较例CA3、CB2由于不含光聚合催化剂,因此弯曲强度显著降低。比较例CA4~CA13和CB4~CB13含有logS大于-4的阴离子与碘鎓阳离子的盐即碘鎓盐化合物。虽然并没有确认这种光致酸产生剂的配合量少的比较例CA4、CA5、CB5、CB6的保存稳定性降低,但是其弯曲强度不充分。像比较例CA6~CA9和比较例CB6~CB9那样,光致酸产生剂的配合量增加时,虽然弯曲强度提高,但在低温保管时确认了析出物,确认了存在弯曲强度降低的倾向。并且,还确认了光颜色稳定性降低。另外,确认了光致酸产生剂的配合量增加的比较例CA10~CA13和比较例CB10~CB13虽然弯曲强度进一步提高,但低温保管时和高温保管时的保存稳定性降低且光颜色稳定性降低。光致酸产生剂的溶解性会影响保存稳定性、颜色稳定性。
通过实施例评价的本发明的牙科用光固化性组合物能够没有任何问题地用于公知的任何的牙科用光固化性组合物。牙科用光固化组合物是牙科用粘接材料、牙科用复合树脂、牙科用基台修筑材料、牙科用树脂水门汀、牙科用涂布材料、牙科用窝沟裂隙封闭材料、牙科用美容材料、牙科用松动牙固定粘接材料、牙科用玻璃离子水门汀、牙科用硬质树脂、牙科切削加工用材料、牙科用3D打印用材料等。
本说明书中,在发明的构成要素为单数或复数的任意一种来进行说明的情况下,或者在未限定为单数或复数来进行说明的情况下,除了从上下文能理解的情况以外,该构成要素可以为单数或复数的任一种。
虽然参照详细的实施方式说明了本发明,但本领域技术人员应该理解基于本说明书中公开的事项能够进行各种变更或修正。因此,意图在于说明本发明的实施方式的范围包括任何改变或修改。
根据本发明,能够提供从低温恢复到室温后也表现出优异的机械物理性质的牙科用光固化性组合物。
Claims (8)
1.一种牙科用光固化性组合物,其中,
其包含(A)聚合性单体、(B)光敏剂、(C)光致酸产生剂以及(D)光聚合促进剂,
并且,(C)光致酸产生剂包含(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。
2.如权利要求1所述的牙科用光固化性组合物,其中,
相对于(A)聚合性单体100质量份,包含0.5质量份以上的(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物。
3.如权利要求1或2所述的牙科用光固化性组合物,其中,
作为(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物,包含由具有有机基团以及P、B、Al、S、Ga中的任意一个以上的原子的阴离子和芳基碘鎓阳离子构成的芳基碘鎓盐。
4.如权利要求1或2所述的牙科用光固化性组合物,其中,
作为(C-1)与logS为-4以下的阴离子形成的碘鎓盐系化合物,包含由具有至少1个以上的H被F取代的有机基团以及P、B、Al、S、Ga中的任意一个以上的原子的阴离子和芳基碘鎓阳离子构成的芳基碘鎓盐。
5.如权利要求1~4中任一项所述的牙科用光固化性组合物,其中,
作为(D)光聚合促进剂包含脂肪族叔胺化合物。
6.如权利要求1~4中任一项所述的牙科用光固化性组合物,其中,
作为(D)光聚合促进剂包含(D-1)不具有2个以上的伯羟基的脂肪族叔胺化合物。
7.如权利要求1~6中任一项所述的牙科用光固化性组合物,其中,
其是单剂型的牙科用光固化性组合物,
相对于(A)聚合性单体100质量份,包含0.005~1.0质量份的(B)光敏剂、0.5~10.0质量份的(C)光致酸产生剂、以及0.01~20质量份的(D)光聚合促进剂。
8.如权利要求1~6中任一项所述的牙科用光固化性组合物,其中,
其是双剂型的牙科用光固化性组合物,
由第一膏和第二膏组成,
第一膏与第二膏的比重为1:0.8~1.2,
相对于第一膏和第二膏中包含的(A)聚合性单体的合计200质量份,包含0.01~2.0质量份的(B)光敏剂、1.0~20质量份的(C)光致酸产生剂、以及0.02~40质量份的(D)光聚合促进剂。
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US20170355857A1 (en) * | 2015-06-08 | 2017-12-14 | Dsm Ip Assets B.V. | Liquid, hybrid uv/vis radiation curable resin compositions for additive fabrication |
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