JP4456859B2 - 歯科用カチオン硬化性組成物 - Google Patents
歯科用カチオン硬化性組成物 Download PDFInfo
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- JP4456859B2 JP4456859B2 JP2003429782A JP2003429782A JP4456859B2 JP 4456859 B2 JP4456859 B2 JP 4456859B2 JP 2003429782 A JP2003429782 A JP 2003429782A JP 2003429782 A JP2003429782 A JP 2003429782A JP 4456859 B2 JP4456859 B2 JP 4456859B2
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- JP
- Japan
- Prior art keywords
- compound
- octane
- trioxabicyclo
- dental
- curable composition
- 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.)
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- 239000000203 mixture Substances 0.000 title claims description 64
- 125000002091 cationic group Chemical group 0.000 title claims description 32
- 150000001875 compounds Chemical class 0.000 claims description 106
- -1 oxetane compound Chemical class 0.000 claims description 77
- 125000000524 functional group Chemical group 0.000 claims description 37
- 239000000463 material Substances 0.000 claims description 30
- 125000003566 oxetanyl group Chemical group 0.000 claims description 26
- 238000011049 filling Methods 0.000 claims description 23
- 239000000945 filler Substances 0.000 claims description 18
- 239000003505 polymerization initiator Substances 0.000 claims description 16
- 238000010538 cationic polymerization reaction Methods 0.000 claims description 14
- 238000006116 polymerization reaction Methods 0.000 description 48
- 239000000178 monomer Substances 0.000 description 30
- 150000003254 radicals Chemical class 0.000 description 21
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 20
- 238000001879 gelation Methods 0.000 description 20
- 230000000704 physical effect Effects 0.000 description 15
- 238000002156 mixing Methods 0.000 description 14
- 239000004593 Epoxy Chemical class 0.000 description 11
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- 239000011256 inorganic filler Substances 0.000 description 10
- 229910003475 inorganic filler Inorganic materials 0.000 description 10
- TVMXDCGIABBOFY-UHFFFAOYSA-N octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 10
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- 125000005520 diaryliodonium group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
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- FNYWFRSQRHGKJT-UHFFFAOYSA-N 3-ethyl-3-[(3-ethyloxetan-3-yl)methoxymethyl]oxetane Chemical compound C1OCC1(CC)COCC1(CC)COC1 FNYWFRSQRHGKJT-UHFFFAOYSA-N 0.000 description 3
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- ITMCEJHCFYSIIV-UHFFFAOYSA-M triflate Chemical compound [O-]S(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-M 0.000 description 3
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- DXBHBZVCASKNBY-UHFFFAOYSA-N 1,2-Benz(a)anthracene Chemical compound C1=CC=C2C3=CC4=CC=CC=C4C=C3C=CC2=C1 DXBHBZVCASKNBY-UHFFFAOYSA-N 0.000 description 2
- AMKRBKSZCGCEJK-UHFFFAOYSA-N 1,2-dimethoxyanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=C(OC)C(OC)=CC=C3C(=O)C2=C1 AMKRBKSZCGCEJK-UHFFFAOYSA-N 0.000 description 2
- APQSQLNWAIULLK-UHFFFAOYSA-N 1,4-dimethylnaphthalene Chemical compound C1=CC=C2C(C)=CC=C(C)C2=C1 APQSQLNWAIULLK-UHFFFAOYSA-N 0.000 description 2
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 description 2
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- QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
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- NJWGQARXZDRHCD-UHFFFAOYSA-N 2-methylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(C)=CC=C3C(=O)C2=C1 NJWGQARXZDRHCD-UHFFFAOYSA-N 0.000 description 2
- MXZKHBKVIJMSHZ-UHFFFAOYSA-N 5,12-dimethyltetracene Chemical compound C1=CC=C2C=C3C(C)=C(C=CC=C4)C4=C(C)C3=CC2=C1 MXZKHBKVIJMSHZ-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- DFPOZTRSOAQFIK-UHFFFAOYSA-N S,S-dimethyl-beta-propiothetin Chemical compound C[S+](C)CCC([O-])=O DFPOZTRSOAQFIK-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 125000005605 benzo group Chemical group 0.000 description 2
- 229930006711 bornane-2,3-dione Natural products 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- 239000002131 composite material Substances 0.000 description 2
- 238000013329 compounding Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000006356 dehydrogenation reaction Methods 0.000 description 2
- 239000003479 dental cement Substances 0.000 description 2
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- 239000000386 donor Substances 0.000 description 2
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- 239000000975 dye Substances 0.000 description 2
- 230000005284 excitation Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- LNTHITQWFMADLM-UHFFFAOYSA-N gallic acid Chemical compound OC(=O)C1=CC(O)=C(O)C(O)=C1 LNTHITQWFMADLM-UHFFFAOYSA-N 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000011159 matrix material Substances 0.000 description 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 2
- AHHWIHXENZJRFG-UHFFFAOYSA-N oxetane Chemical group C1COC1 AHHWIHXENZJRFG-UHFFFAOYSA-N 0.000 description 2
- 125000002080 perylenyl group Chemical group C1(=CC=C2C=CC=C3C4=CC=CC5=CC=CC(C1=C23)=C45)* 0.000 description 2
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- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
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- 238000007142 ring opening reaction Methods 0.000 description 2
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JNELGWHKGNBSMD-UHFFFAOYSA-N xanthone Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3OC2=C1 JNELGWHKGNBSMD-UHFFFAOYSA-N 0.000 description 2
- JERBUBCQUQOHIC-UHFFFAOYSA-N (1-acetyloxy-9,10-dioxoanthracen-2-yl) acetate Chemical compound C1=CC=C2C(=O)C3=C(OC(C)=O)C(OC(=O)C)=CC=C3C(=O)C2=C1 JERBUBCQUQOHIC-UHFFFAOYSA-N 0.000 description 1
- LYSHHOCLJPXCCT-UHFFFAOYSA-N (1-ethyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methyl 2-methylprop-2-enoate Chemical compound C(C)C12OCC(CO1)(CO2)COC(C(=C)C)=O LYSHHOCLJPXCCT-UHFFFAOYSA-N 0.000 description 1
- RYDWUOPDUKLZQF-UHFFFAOYSA-N (1-ethyl-2,6,7-trioxabicyclo[2.2.2]octan-4-yl)methyl benzoate Chemical compound C(C)C12OCC(CO1)(CO2)COC(C2=CC=CC=C2)=O RYDWUOPDUKLZQF-UHFFFAOYSA-N 0.000 description 1
- DNEOMNDSVDVAKL-UHFFFAOYSA-N (1-ethyl-3,5,8-trioxabicyclo[2.2.2]octan-4-yl)methanol Chemical compound C1OC2(CO)OCC1(CC)CO2 DNEOMNDSVDVAKL-UHFFFAOYSA-N 0.000 description 1
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- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
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- DWBJZABVMXQFPV-UHFFFAOYSA-N bis(4-methoxyphenyl)iodanium Chemical compound C1=CC(OC)=CC=C1[I+]C1=CC=C(OC)C=C1 DWBJZABVMXQFPV-UHFFFAOYSA-N 0.000 description 1
- DNFSNYQTQMVTOK-UHFFFAOYSA-N bis(4-tert-butylphenyl)iodanium Chemical compound C1=CC(C(C)(C)C)=CC=C1[I+]C1=CC=C(C(C)(C)C)C=C1 DNFSNYQTQMVTOK-UHFFFAOYSA-N 0.000 description 1
- UIZLQMLDSWKZGC-UHFFFAOYSA-N cadmium helium Chemical compound [He].[Cd] UIZLQMLDSWKZGC-UHFFFAOYSA-N 0.000 description 1
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- SNVTZAIYUGUKNI-UHFFFAOYSA-N dibenzo[1,2-a:1',2'-e][7]annulen-11-one Chemical compound C1=CC2=CC=CC=C2C(=O)C2=CC=CC=C21 SNVTZAIYUGUKNI-UHFFFAOYSA-N 0.000 description 1
- VEWACKLSAWIQFX-UHFFFAOYSA-N dihydroxy(naphthalen-1-yl)sulfanium Chemical compound O[S+](C1=CC=CC2=CC=CC=C12)O VEWACKLSAWIQFX-UHFFFAOYSA-N 0.000 description 1
- JTNDNBUJMQNEGL-UHFFFAOYSA-N dimethyl(phenacyl)sulfanium Chemical compound C[S+](C)CC(=O)C1=CC=CC=C1 JTNDNBUJMQNEGL-UHFFFAOYSA-N 0.000 description 1
- OWZDULOODZHVCQ-UHFFFAOYSA-N diphenyl-(4-phenylsulfanylphenyl)sulfanium Chemical compound C=1C=C([S+](C=2C=CC=CC=2)C=2C=CC=CC=2)C=CC=1SC1=CC=CC=C1 OWZDULOODZHVCQ-UHFFFAOYSA-N 0.000 description 1
- OZLBDYMWFAHSOQ-UHFFFAOYSA-N diphenyliodanium Chemical compound C=1C=CC=CC=1[I+]C1=CC=CC=C1 OZLBDYMWFAHSOQ-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 238000011156 evaluation Methods 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
- YLQWCDOCJODRMT-UHFFFAOYSA-N fluoren-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3C2=C1 YLQWCDOCJODRMT-UHFFFAOYSA-N 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- AVIYEYCFMVPYST-UHFFFAOYSA-N hexane-1,3-diol Chemical compound CCCC(O)CCO AVIYEYCFMVPYST-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000000852 hydrogen donor Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 239000010954 inorganic particle Substances 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- HEBMCVBCEDMUOF-UHFFFAOYSA-N isochromane Chemical compound C1=CC=C2COCCC2=C1 HEBMCVBCEDMUOF-UHFFFAOYSA-N 0.000 description 1
- BSIHWSXXPBAGTC-UHFFFAOYSA-N isoviolanthrone Chemical compound C12=CC=CC=C2C(=O)C2=CC=C3C(C4=C56)=CC=C5C5=CC=CC=C5C(=O)C6=CC=C4C4=C3C2=C1C=C4 BSIHWSXXPBAGTC-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229910052746 lanthanum Inorganic materials 0.000 description 1
- FZLIPJUXYLNCLC-UHFFFAOYSA-N lanthanum atom Chemical compound [La] FZLIPJUXYLNCLC-UHFFFAOYSA-N 0.000 description 1
- 229910001507 metal halide Inorganic materials 0.000 description 1
- 150000005309 metal halides Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- SJGATVMDXUPPIC-UHFFFAOYSA-N n,n,10-trimethylanthracen-9-amine Chemical compound C1=CC=C2C(N(C)C)=C(C=CC=C3)C3=C(C)C2=C1 SJGATVMDXUPPIC-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- 229920000847 nonoxynol Polymers 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- UFCVADNIXDUEFZ-UHFFFAOYSA-N pentacene-6,13-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC5=CC=CC=C5C=C4C(=O)C3=CC2=C1 UFCVADNIXDUEFZ-UHFFFAOYSA-N 0.000 description 1
- TZMFJUDUGYTVRY-UHFFFAOYSA-N pentane-2,3-dione Chemical compound CCC(=O)C(C)=O TZMFJUDUGYTVRY-UHFFFAOYSA-N 0.000 description 1
- NQFOGDIWKQWFMN-UHFFFAOYSA-N phenalene Chemical compound C1=CC([CH]C=C2)=C3C2=CC=CC3=C1 NQFOGDIWKQWFMN-UHFFFAOYSA-N 0.000 description 1
- 229950000688 phenothiazine Drugs 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- SFLGSKRGOWRGBR-UHFFFAOYSA-N phthalane Chemical compound C1=CC=C2COCC2=C1 SFLGSKRGOWRGBR-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
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- 229920001155 polypropylene Polymers 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
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- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- 229920003048 styrene butadiene rubber Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- IFLREYGFSNHWGE-UHFFFAOYSA-N tetracene Chemical compound C1=CC=CC2=CC3=CC4=CC=CC=C4C=C3C=C21 IFLREYGFSNHWGE-UHFFFAOYSA-N 0.000 description 1
- LZPBKINTWROMEA-UHFFFAOYSA-N tetracene-5,12-dione Chemical compound C1=CC=C2C=C3C(=O)C4=CC=CC=C4C(=O)C3=CC2=C1 LZPBKINTWROMEA-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
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- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 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
- WLOQLWBIJZDHET-UHFFFAOYSA-N triphenylsulfonium Chemical compound C1=CC=CC=C1[S+](C=1C=CC=CC=1)C1=CC=CC=C1 WLOQLWBIJZDHET-UHFFFAOYSA-N 0.000 description 1
- 239000012953 triphenylsulfonium Substances 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 229910052721 tungsten Inorganic materials 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
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Landscapes
- Dental Preparations (AREA)
- Polyethers (AREA)
Description
で示される四員環エーテル(オキセタン環)官能基であり、ビシクロオルトエステル官能基とは、下記式(2)
で示されるビシクロオルトエステル環からなる官能基である。
1.オキセタン化合物
CQ:カンファーキノン
8.その他
DMPT:N,N−ジメチル−p−トルイジン
また、本文中ならびに実施例中に示した物性評価方法については次の通りである。
ガラス板上に、約直径6mm、高さ3mmに硬化性組成物を築盛し、築盛物上面約5mmの距離から歯科用光照射器(TOKUSO POWER LITE、(株)トクヤマデンタル社製)により可視光を照射した。そのとき、太さ約0.4mmの針で照射光を遮らない様、築盛物上面および側面の硬さを調べ、築盛物全体に針が刺さらなくなった時を硬化時間とした。
ガラス板上に、調製した硬化性組成物を直径6mm、高さ3mmの円盤状に築盛した。次に硬化性組成物を載せたガラス面方向から約5mm離して歯科用照射機(TOKUSO POWER LITE、(株)トクヤマデンタル社製)で硬化性組成物に対して照射を開始した。この光照射を行いつつガラス面の反対側から、築盛した硬化性組成物に針を接触させて探り、この部分に流動性が認められなくなった時点をゲル化時間とした。
直径3mm、高さ7mmの孔を有するSUS製割型に、直径3mm、高さ4mmのSUS製プランジャーを填入して孔の高さを3mmとした。これに硬化性組成物を充填し、上からポリプロピレンフィルムで圧接した。フィルム面を下に向けて歯科用照射器の備え付けてあるガラス製台の上に載せ、更にSUS製プランジャーの上から微小な針の動きを計測できる短針を接触させた。歯科用照射器によって重合硬化させ、照射開始より10分後の収縮(%)を、短針の上下方向の移動距離から算出した。
硬化性組成物を2×2×25mmの金型に充填し、光照射器にて1.5分間光照射し硬化させた。硬化物を37℃で一晩保存した後、オートグラフ(島津製作所社製)を使用し、支点間距離20mm、クロスヘッドスピード0.5mm/分で3点曲げ強度と曲げ弾性率を各々5個の硬化物について測定し、その平均値を算出した。
OXT−121(東亜合成社製)とBOE−1とを、OXT−121が1モルに対して、BOE−1が0.1053モルとなるように量を調節して配合した。この場合、OXT−121は2官能のオキセタン化合物であるからaが2、BOE−1は単官能のビシクロオルトエステル化合物であるからbが1であり、官能基割合は(a×A):(b×B)=(2×1):(1×0.1053)=95:5となる。
OXT−121とBOE−1との混合物に代えて、全てOXT−121を用いた以外は実施例1と同様にして歯科用充填修復材料を調整し、各種物性を測定した。その結果、ゲル化時間が7秒、硬化時間が33秒、重合収縮率が1.1%であった。
OXT−121とBOE−1との混合比を表1に示す割合で変化させて各種物性を測定した。なお表中、オキセタン化合物の欄の数値は(a×A)+(b×B)を100とした場合の(a×A)を、ビシクロオルトエステル化合物の欄の数値は(b×B)を示す。測定された物性を表1に示す。
OXT−121とBOE−1との混合物に代えて、全てBOE−1を用いた以外は実施例1と同様にして歯科用充填修復材料を調整し、各種物性を測定しようとしたが、10分間の光照射でも全く硬化しなかった。
BOE−1に代えて、BOE−2を用い、これとOXT−121との混合比を表1に示す割合で変化させて各種物性を測定した。なお表中、オキセタン化合物の欄の数値は(a×A)+(b×B)を100とした場合の(a×A)を、ビシクロオルトエステル化合物の欄の数値は(b×B)を示す。測定された物性を表1に示す。
OXT−121とBOE−1との混合物に代えて、OXT−221を100%とした以外は実施例1と同様にして歯科用充填修復材料を調整し、各種物性を測定した。その結果、ゲル化時間が6秒、硬化時間が30秒、重合収縮率が1.2%であった。
OXT−121に代えて、OXT−221を用い、これとBOE−1との混合比を表1に示す割合で変化させて各種物性を測定した。なお表中、オキセタン化合物の欄の数値は(a×A)+(b×B)を100とした場合の(a×A)を、ビシクロオルトエステル化合物の欄の数値は(b×B)を示す。測定された物性を表1に示す。
表2に示す官能基割合になるように、各種カチオン重合性化合物を所定量配合し、実施例1と同じ割合で光カチオン重合開始剤を加えて歯科用充填修復材を得た。これらの組成物のゲル化時間、硬化時間及び重合収縮率を測定し、結果を表2に示した。なお表中、各化合物の欄の数値は、組成物中の全カチオン重合性官能基の総和を100とした場合の、各々の化合物に由来するカチオン重合性官能基の割合を示す値であり、その計算方法は前記オキセタン官能基及びビシクロオルトエステル官能基の場合と同様である。
ラジカル重合性化合物であるBis−GMAを50質量部と、3Gを50質量部混合し、この混合物に対してDMPTを1質量部、CQを0.4質量部加えて暗所で攪拌溶解した。
Claims (4)
- (I)カチオン重合開始剤と(II)カチオン重合性化合物とを含む硬化性組成物において、該(II)カチオン重合性化合物は、1分子あたりa個のオキセタン官能基を有するオキセタン化合物をAモルと、1分子あたりb個のビシクロオルトエステル官能基を有するビシクロオルトエステル化合物をBモルとを含んでなり、かつ、(a×A):(b×B)が99.99:0.01〜50:50の範囲にあることを特徴とする歯科用カチオン硬化性組成物。
- (I)カチオン重合開始剤が光カチオン重合開始剤である請求項1記載の歯科用カチオン硬化性組成物。
- さらに、(III)充填材を含む請求項1又は2記載の歯科用カチオン硬化性組成物。
- 歯科用充填修復材料であることを特徴とする請求項1〜3記載の歯科用カチオン硬化性組成物。
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JP4859408B2 (ja) * | 2005-07-22 | 2012-01-25 | 株式会社トクヤマ | 歯科用カチオン硬化性組成物 |
JP5931057B2 (ja) | 2011-05-16 | 2016-06-08 | 三井化学株式会社 | 歯科材料、歯科材料組成物、歯科修復材料および硬化物 |
JP5819415B2 (ja) | 2011-05-16 | 2015-11-24 | 三井化学株式会社 | 新規な化合物、該化合物を含む組成物および硬化物 |
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