CN1865295A - Curable composition - Google Patents
Curable composition Download PDFInfo
- Publication number
- CN1865295A CN1865295A CN 200610079371 CN200610079371A CN1865295A CN 1865295 A CN1865295 A CN 1865295A CN 200610079371 CN200610079371 CN 200610079371 CN 200610079371 A CN200610079371 A CN 200610079371A CN 1865295 A CN1865295 A CN 1865295A
- Authority
- CN
- China
- Prior art keywords
- water
- mass parts
- polymerization
- monomer
- solidification compound
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 99
- 239000000178 monomer Substances 0.000 claims abstract description 163
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 156
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 148
- 239000004094 surface-active agent Substances 0.000 claims abstract description 4
- 239000007870 radical polymerization initiator Substances 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 105
- 238000007711 solidification Methods 0.000 claims description 88
- 230000008023 solidification Effects 0.000 claims description 88
- 238000010521 absorption reaction Methods 0.000 claims description 82
- 239000013543 active substance Substances 0.000 claims description 60
- 239000000463 material Substances 0.000 claims description 39
- 239000003945 anionic surfactant Substances 0.000 claims description 22
- 239000002736 nonionic surfactant Substances 0.000 claims description 19
- 229920003169 water-soluble polymer Polymers 0.000 claims description 15
- 230000008439 repair process Effects 0.000 claims description 12
- 238000010526 radical polymerization reaction Methods 0.000 claims description 9
- 230000015572 biosynthetic process Effects 0.000 abstract description 27
- 239000001301 oxygen Substances 0.000 abstract description 20
- 229910052760 oxygen Inorganic materials 0.000 abstract description 20
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 abstract description 19
- 230000003247 decreasing effect Effects 0.000 abstract 1
- -1 Methacrylic acid hydroxyl pentyl ester Chemical class 0.000 description 100
- 230000009102 absorption Effects 0.000 description 79
- 235000019333 sodium laurylsulphate Nutrition 0.000 description 67
- 230000000052 comparative effect Effects 0.000 description 35
- 239000000126 substance Substances 0.000 description 34
- CERQOIWHTDAKMF-UHFFFAOYSA-N alpha-methacrylic acid Natural products CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 33
- 239000007858 starting material Substances 0.000 description 32
- 102100026735 Coagulation factor VIII Human genes 0.000 description 24
- 101000911390 Homo sapiens Coagulation factor VIII Proteins 0.000 description 24
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 24
- IBDVWXAVKPRHCU-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 3-oxobutanoate Chemical compound CC(=O)CC(=O)OCCOC(=O)C(C)=C IBDVWXAVKPRHCU-UHFFFAOYSA-N 0.000 description 22
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 22
- 239000004342 Benzoyl peroxide Substances 0.000 description 21
- 235000019400 benzoyl peroxide Nutrition 0.000 description 21
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 15
- 229910052796 boron Inorganic materials 0.000 description 15
- 150000003839 salts Chemical class 0.000 description 15
- AMFGWXWBFGVCKG-UHFFFAOYSA-N Panavia opaque Chemical compound C1=CC(OCC(O)COC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCC(O)COC(=O)C(C)=C)C=C1 AMFGWXWBFGVCKG-UHFFFAOYSA-N 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 14
- 239000013047 polymeric layer Substances 0.000 description 14
- DFPOZTRSOAQFIK-UHFFFAOYSA-N S,S-dimethyl-beta-propiothetin Chemical compound C[S+](C)CCC([O-])=O DFPOZTRSOAQFIK-UHFFFAOYSA-N 0.000 description 13
- 239000010410 layer Substances 0.000 description 13
- 238000000034 method Methods 0.000 description 13
- 230000000379 polymerizing effect Effects 0.000 description 13
- 239000007788 liquid Substances 0.000 description 12
- 239000000945 filler Substances 0.000 description 11
- 239000001294 propane Substances 0.000 description 11
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 10
- 238000011156 evaluation Methods 0.000 description 10
- 239000003999 initiator Substances 0.000 description 10
- 238000002156 mixing Methods 0.000 description 10
- 230000004888 barrier function Effects 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
- 238000005498 polishing Methods 0.000 description 9
- 238000002360 preparation method Methods 0.000 description 9
- 239000011347 resin Substances 0.000 description 8
- 229920005989 resin Polymers 0.000 description 8
- OUUQCZGPVNCOIJ-UHFFFAOYSA-M Superoxide Chemical compound [O-][O] OUUQCZGPVNCOIJ-UHFFFAOYSA-M 0.000 description 7
- 239000002253 acid Substances 0.000 description 7
- 239000012764 mineral filler Substances 0.000 description 7
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 6
- 150000002978 peroxides Chemical class 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- 238000003860 storage Methods 0.000 description 6
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 5
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 150000002170 ethers Chemical class 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 5
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 4
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 4
- CMEWLCATCRTSGF-UHFFFAOYSA-N N,N-dimethyl-4-nitrosoaniline Chemical compound CN(C)C1=CC=C(N=O)C=C1 CMEWLCATCRTSGF-UHFFFAOYSA-N 0.000 description 4
- XHCLAFWTIXFWPH-UHFFFAOYSA-N [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[V+5].[V+5] XHCLAFWTIXFWPH-UHFFFAOYSA-N 0.000 description 4
- 230000002378 acidificating effect Effects 0.000 description 4
- 125000000217 alkyl group Chemical group 0.000 description 4
- 238000005461 lubrication Methods 0.000 description 4
- 239000011159 matrix material Substances 0.000 description 4
- 210000000214 mouth Anatomy 0.000 description 4
- WKGDNXBDNLZSKC-UHFFFAOYSA-N oxido(phenyl)phosphanium Chemical class O=[PH2]c1ccccc1 WKGDNXBDNLZSKC-UHFFFAOYSA-N 0.000 description 4
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 238000013112 stability test Methods 0.000 description 4
- 238000009736 wetting Methods 0.000 description 4
- FFJCNSLCJOQHKM-CLFAGFIQSA-N (z)-1-[(z)-octadec-9-enoxy]octadec-9-ene Chemical compound CCCCCCCC\C=C/CCCCCCCCOCCCCCCCC\C=C/CCCCCCCC FFJCNSLCJOQHKM-CLFAGFIQSA-N 0.000 description 3
- XILIYVSXLSWUAI-UHFFFAOYSA-N 2-(diethylamino)ethyl n'-phenylcarbamimidothioate;dihydrobromide Chemical compound Br.Br.CCN(CC)CCSC(N)=NC1=CC=CC=C1 XILIYVSXLSWUAI-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- JDKSTARXLKKYPS-UHFFFAOYSA-N 2-[10-(2-methylprop-2-enoyloxy)decyl]propanedioic acid Chemical compound CC(=C)C(=O)OCCCCCCCCCCC(C(O)=O)C(O)=O JDKSTARXLKKYPS-UHFFFAOYSA-N 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 3
- SAPGBCWOQLHKKZ-UHFFFAOYSA-N 6-(2-methylprop-2-enoyloxy)hexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCOC(=O)C(C)=C SAPGBCWOQLHKKZ-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- 229930182556 Polyacetal Natural products 0.000 description 3
- 239000004372 Polyvinyl alcohol Substances 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Polymers CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 3
- QUZSUMLPWDHKCJ-UHFFFAOYSA-N bisphenol A dimethacrylate Chemical compound C1=CC(OC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OC(=O)C(C)=C)C=C1 QUZSUMLPWDHKCJ-UHFFFAOYSA-N 0.000 description 3
- 230000008859 change Effects 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000001723 curing Methods 0.000 description 3
- 239000005548 dental material Substances 0.000 description 3
- 239000012933 diacyl peroxide Substances 0.000 description 3
- 238000007046 ethoxylation reaction Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000012766 organic filler Substances 0.000 description 3
- 239000005022 packaging material Substances 0.000 description 3
- 230000037048 polymerization activity Effects 0.000 description 3
- 229920006324 polyoxymethylene Polymers 0.000 description 3
- 229920002451 polyvinyl alcohol Polymers 0.000 description 3
- 238000005057 refrigeration Methods 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 229910021653 sulphate ion Inorganic materials 0.000 description 3
- 238000004381 surface treatment Methods 0.000 description 3
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical class CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 3
- 150000003682 vanadium compounds Chemical class 0.000 description 3
- 229910001935 vanadium oxide Inorganic materials 0.000 description 3
- COHYOLUPIYKLBI-UHFFFAOYSA-N (2,3,5,6-tetraethoxy-4-propylphenyl) 2-methylprop-2-enoate Chemical compound CCCC1=C(OCC)C(OCC)=C(OC(=O)C(C)=C)C(OCC)=C1OCC COHYOLUPIYKLBI-UHFFFAOYSA-N 0.000 description 2
- GIYLECFPSJNUDC-UHFFFAOYSA-N (2,3-diethoxy-4-propylphenyl) 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OC(=O)C(C)=C)C(OCC)=C1OCC GIYLECFPSJNUDC-UHFFFAOYSA-N 0.000 description 2
- UFYXQBDPCNVQJS-UHFFFAOYSA-N (2,3-dipropoxy-4-propylphenyl) 2-methylprop-2-enoate Chemical compound CCCOC1=C(CCC)C=CC(OC(=O)C(C)=C)=C1OCCC UFYXQBDPCNVQJS-UHFFFAOYSA-N 0.000 description 2
- PUSGTXMDMADRPN-UHFFFAOYSA-N (2-nitrophenyl)boron Chemical compound [B]C1=CC=CC=C1[N+]([O-])=O PUSGTXMDMADRPN-UHFFFAOYSA-N 0.000 description 2
- SZVDCXKETCPZOL-UHFFFAOYSA-N (2-propylphenyl) 2-methylprop-2-enoate Chemical compound CCCC1=CC=CC=C1OC(=O)C(C)=C SZVDCXKETCPZOL-UHFFFAOYSA-N 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 2
- SPBFJDAYGAIKCF-UHFFFAOYSA-N (4-propylphenyl) 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OC(=O)C(C)=C)C=C1 SPBFJDAYGAIKCF-UHFFFAOYSA-N 0.000 description 2
- OKIRBHVFJGXOIS-UHFFFAOYSA-N 1,2-di(propan-2-yl)benzene Chemical compound CC(C)C1=CC=CC=C1C(C)C OKIRBHVFJGXOIS-UHFFFAOYSA-N 0.000 description 2
- VDYWHVQKENANGY-UHFFFAOYSA-N 1,3-Butyleneglycol dimethacrylate Chemical compound CC(=C)C(=O)OC(C)CCOC(=O)C(C)=C VDYWHVQKENANGY-UHFFFAOYSA-N 0.000 description 2
- REACWASHYHDPSQ-UHFFFAOYSA-N 1-butylpyridin-1-ium Chemical compound CCCC[N+]1=CC=CC=C1 REACWASHYHDPSQ-UHFFFAOYSA-N 0.000 description 2
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- ZHKBLALOBMBJLL-UHFFFAOYSA-N 1-hexylperoxyhexane Chemical compound CCCCCCOOCCCCCC ZHKBLALOBMBJLL-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- LTHJXDSHSVNJKG-UHFFFAOYSA-N 2-[2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCOC(=O)C(C)=C LTHJXDSHSVNJKG-UHFFFAOYSA-N 0.000 description 2
- GMZLALYCWQSOQS-UHFFFAOYSA-N 2-butylquinoline Chemical compound C1=CC=CC2=NC(CCCC)=CC=C21 GMZLALYCWQSOQS-UHFFFAOYSA-N 0.000 description 2
- JMWGZSWSTCGVLX-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;2-methylprop-2-enoic acid Polymers CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CCC(CO)(CO)CO JMWGZSWSTCGVLX-UHFFFAOYSA-N 0.000 description 2
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 2
- XCIZVKSCLVSDHN-UHFFFAOYSA-N 2-ethylquinoline Chemical compound C1=CC=CC2=NC(CC)=CC=C21 XCIZVKSCLVSDHN-UHFFFAOYSA-N 0.000 description 2
- MIRQGKQPLPBZQM-UHFFFAOYSA-N 2-hydroperoxy-2,4,4-trimethylpentane Chemical compound CC(C)(C)CC(C)(C)OO MIRQGKQPLPBZQM-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 2
- VBFUPMRXHGTXTL-UHFFFAOYSA-N 3-(4-propylphenoxy)propyl 2-methylprop-2-enoate Chemical compound CCCC1=CC=C(OCCCOC(=O)C(C)=C)C=C1 VBFUPMRXHGTXTL-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 2
- VHYFNPMBLIVWCW-UHFFFAOYSA-N 4-Dimethylaminopyridine Chemical compound CN(C)C1=CC=NC=C1 VHYFNPMBLIVWCW-UHFFFAOYSA-N 0.000 description 2
- YJVIKVWFGPLAFS-UHFFFAOYSA-N 9-(2-methylprop-2-enoyloxy)nonyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCCOC(=O)C(C)=C YJVIKVWFGPLAFS-UHFFFAOYSA-N 0.000 description 2
- HJVHDIGCIITVIO-UHFFFAOYSA-N C(C(=C)C)(=O)OC1=CC(=C(C=C1)CCC)C(C)C Chemical compound C(C(=C)C)(=O)OC1=CC(=C(C=C1)CCC)C(C)C HJVHDIGCIITVIO-UHFFFAOYSA-N 0.000 description 2
- AYDRQTGVLWHHFS-UHFFFAOYSA-N C(CCC)C1=C(C=CC=C1)[B] Chemical compound C(CCC)C1=C(C=CC=C1)[B] AYDRQTGVLWHHFS-UHFFFAOYSA-N 0.000 description 2
- NOCAMODJIZSPEQ-UHFFFAOYSA-N C(CCC)OC1=C(C=CC=C1)[B] Chemical compound C(CCC)OC1=C(C=CC=C1)[B] NOCAMODJIZSPEQ-UHFFFAOYSA-N 0.000 description 2
- CBKKAMQXPMPXGV-UHFFFAOYSA-N C(CCCCCCC)OC1=C(C=CC=C1)[B] Chemical compound C(CCCCCCC)OC1=C(C=CC=C1)[B] CBKKAMQXPMPXGV-UHFFFAOYSA-N 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- 239000004141 Sodium laurylsulphate Substances 0.000 description 2
- 229920002125 Sokalan® Polymers 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical class OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- FSDJQMOZRWOIRG-UHFFFAOYSA-N [2,3-dipropoxy-4-[2-[2,3,5-triethoxy-4-(2-methylprop-2-enoyloxy)phenyl]propyl]phenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(C)=C)=C(OCCC)C(OCCC)=C1CC(C)C1=CC(OCC)=C(OC(=O)C(C)=C)C(OCC)=C1OCC FSDJQMOZRWOIRG-UHFFFAOYSA-N 0.000 description 2
- NFNKGIYWQDTWKO-UHFFFAOYSA-N [4-[2-[2,3-diethoxy-4-(2-methylprop-2-enoyloxy)phenyl]propyl]-2,3-diethoxyphenyl] 2-methylprop-2-enoate Chemical compound C1=CC(OC(=O)C(C)=C)=C(OCC)C(OCC)=C1CC(C)C1=CC=C(OC(=O)C(C)=C)C(OCC)=C1OCC NFNKGIYWQDTWKO-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical class CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- 125000000129 anionic group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- JEHKKBHWRAXMCH-UHFFFAOYSA-N benzenesulfinic acid Chemical compound O[S@@](=O)C1=CC=CC=C1 JEHKKBHWRAXMCH-UHFFFAOYSA-N 0.000 description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 2
- 239000012965 benzophenone Substances 0.000 description 2
- 150000001639 boron compounds Chemical class 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N butan-1-amine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- 239000003093 cationic surfactant Substances 0.000 description 2
- IJOOHPMOJXWVHK-UHFFFAOYSA-N chlorotrimethylsilane Chemical compound C[Si](C)(C)Cl IJOOHPMOJXWVHK-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 238000007865 diluting Methods 0.000 description 2
- GNTDGMZSJNCJKK-UHFFFAOYSA-N divanadium pentaoxide Chemical compound O=[V](=O)O[V](=O)=O GNTDGMZSJNCJKK-UHFFFAOYSA-N 0.000 description 2
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
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- WTIFDVLCDRBEJK-VAWYXSNFSA-N diphenyl (e)-but-2-enedioate Chemical compound C=1C=CC=CC=1OC(=O)/C=C/C(=O)OC1=CC=CC=C1 WTIFDVLCDRBEJK-VAWYXSNFSA-N 0.000 description 1
- VFHVQBAGLAREND-UHFFFAOYSA-N diphenylphosphoryl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 VFHVQBAGLAREND-UHFFFAOYSA-N 0.000 description 1
- HZWAUDKTZOUQPD-UHFFFAOYSA-N diphenylphosphoryl-(2-methylphenyl)methanone Chemical compound CC1=CC=CC=C1C(=O)P(=O)(C=1C=CC=CC=1)C1=CC=CC=C1 HZWAUDKTZOUQPD-UHFFFAOYSA-N 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- SYELZBGXAIXKHU-UHFFFAOYSA-N dodecyldimethylamine N-oxide Chemical compound CCCCCCCCCCCC[N+](C)(C)[O-] SYELZBGXAIXKHU-UHFFFAOYSA-N 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- FWDBOZPQNFPOLF-UHFFFAOYSA-N ethenyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)C=C FWDBOZPQNFPOLF-UHFFFAOYSA-N 0.000 description 1
- 125000002573 ethenylidene group Chemical group [*]=C=C([H])[H] 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 229920001038 ethylene copolymer Polymers 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000005383 fluoride glass Substances 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- PYGSKMBEVAICCR-UHFFFAOYSA-N hexa-1,5-diene Chemical group C=CCCC=C PYGSKMBEVAICCR-UHFFFAOYSA-N 0.000 description 1
- FFUAGWLWBBFQJT-UHFFFAOYSA-N hexamethyldisilazane Chemical class C[Si](C)(C)N[Si](C)(C)C FFUAGWLWBBFQJT-UHFFFAOYSA-N 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 150000002500 ions 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
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- ZEJSPRHJSJUARL-UHFFFAOYSA-N methoxy-[2-(2,4,6-trimethylbenzoyl)phenyl]phosphinic acid Chemical class COP(O)(=O)C1=CC=CC=C1C(=O)C1=C(C)C=C(C)C=C1C ZEJSPRHJSJUARL-UHFFFAOYSA-N 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000005055 methyl trichlorosilane Substances 0.000 description 1
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 1
- BFXIKLCIZHOAAZ-UHFFFAOYSA-N methyltrimethoxysilane Chemical compound CO[Si](C)(OC)OC BFXIKLCIZHOAAZ-UHFFFAOYSA-N 0.000 description 1
- NKHAVTQWNUWKEO-NSCUHMNNSA-N monomethyl fumarate Chemical compound COC(=O)\C=C\C(O)=O NKHAVTQWNUWKEO-NSCUHMNNSA-N 0.000 description 1
- 229940005650 monomethyl fumarate Drugs 0.000 description 1
- FZPXKEPZZOEPGX-UHFFFAOYSA-N n,n-dibutylaniline Chemical compound CCCCN(CCCC)C1=CC=CC=C1 FZPXKEPZZOEPGX-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- IKZPRXHVTFNIEK-UHFFFAOYSA-N n,n-dimethylnaphthalen-2-amine Chemical compound C1=CC=CC2=CC(N(C)C)=CC=C21 IKZPRXHVTFNIEK-UHFFFAOYSA-N 0.000 description 1
- VYHUMZYFJVMWRC-UHFFFAOYSA-N n-(2-hydroxyethyl)-n-methylprop-2-enamide Chemical compound OCCN(C)C(=O)C=C VYHUMZYFJVMWRC-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 230000033116 oxidation-reduction process Effects 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- CFHIDWOYWUOIHU-UHFFFAOYSA-N oxomethyl Chemical compound O=[CH] CFHIDWOYWUOIHU-UHFFFAOYSA-N 0.000 description 1
- HEHINIICWNIGNO-UHFFFAOYSA-N oxosilicon;titanium Chemical compound [Ti].[Si]=O HEHINIICWNIGNO-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 235000011837 pasties Nutrition 0.000 description 1
- 239000003415 peat Substances 0.000 description 1
- 229940059574 pentaerithrityl Drugs 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000004978 peroxycarbonates Chemical class 0.000 description 1
- 229940067107 phenylethyl alcohol Drugs 0.000 description 1
- 235000021317 phosphate Nutrition 0.000 description 1
- 125000001476 phosphono group Chemical group [H]OP(*)(=O)O[H] 0.000 description 1
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 229920001495 poly(sodium acrylate) polymer Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- BOQSSGDQNWEFSX-UHFFFAOYSA-N propan-2-yl 2-methylprop-2-enoate Chemical compound CC(C)OC(=O)C(C)=C BOQSSGDQNWEFSX-UHFFFAOYSA-N 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
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 239000001327 prunus amygdalus amara l. extract Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229960001866 silicon dioxide Drugs 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- BTURAGWYSMTVOW-UHFFFAOYSA-M sodium dodecanoate Chemical compound [Na+].CCCCCCCCCCCC([O-])=O BTURAGWYSMTVOW-UHFFFAOYSA-M 0.000 description 1
- 229940082004 sodium laurate Drugs 0.000 description 1
- CMZUMMUJMWNLFH-UHFFFAOYSA-N sodium metavanadate Chemical compound [Na+].[O-][V](=O)=O CMZUMMUJMWNLFH-UHFFFAOYSA-N 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- AJVIQNYVMGYYOL-UHFFFAOYSA-M sodium;2-decylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O AJVIQNYVMGYYOL-UHFFFAOYSA-M 0.000 description 1
- AIMUHNZKNFEZSN-UHFFFAOYSA-M sodium;decane-1-sulfonate Chemical compound [Na+].CCCCCCCCCCS([O-])(=O)=O AIMUHNZKNFEZSN-UHFFFAOYSA-M 0.000 description 1
- QWSZRRAAFHGKCH-UHFFFAOYSA-M sodium;hexane-1-sulfonate Chemical compound [Na+].CCCCCCS([O-])(=O)=O QWSZRRAAFHGKCH-UHFFFAOYSA-M 0.000 description 1
- 235000021286 stilbenes Nutrition 0.000 description 1
- 230000000638 stimulation Effects 0.000 description 1
- 229910052712 strontium Inorganic materials 0.000 description 1
- CIOAGBVUUVVLOB-UHFFFAOYSA-N strontium atom Chemical compound [Sr] CIOAGBVUUVVLOB-UHFFFAOYSA-N 0.000 description 1
- UUCCCPNEFXQJEL-UHFFFAOYSA-L strontium dihydroxide Chemical compound [OH-].[OH-].[Sr+2] UUCCCPNEFXQJEL-UHFFFAOYSA-L 0.000 description 1
- 229910001866 strontium hydroxide Inorganic materials 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000012756 surface treatment agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 235000012976 tarts Nutrition 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
- MVQLEZWPIWKLBY-UHFFFAOYSA-N tert-butyl 2-benzoylbenzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)C1=CC=CC=C1 MVQLEZWPIWKLBY-UHFFFAOYSA-N 0.000 description 1
- CVSOCRZKKCPWHD-UHFFFAOYSA-N tert-butylperoxycyclodecane Chemical compound C(C)(C)(C)OOC1CCCCCCCCC1 CVSOCRZKKCPWHD-UHFFFAOYSA-N 0.000 description 1
- 238000002560 therapeutic procedure Methods 0.000 description 1
- 238000012719 thermal polymerization Methods 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
- 210000001519 tissue Anatomy 0.000 description 1
- 239000010936 titanium Substances 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
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 239000005051 trimethylchlorosilane Substances 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- MXSVLWZRHLXFKH-UHFFFAOYSA-N triphenylborane Chemical compound C1=CC=CC=C1B(C=1C=CC=CC=1)C1=CC=CC=C1 MXSVLWZRHLXFKH-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 description 1
- 229910052720 vanadium Inorganic materials 0.000 description 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
A curable composition comprising: (A) 100 parts by mass of a monomer component which comprises a radically polymerizable monomer and has a water absorbing capacity of not larger than 20% by weight; (B) 0.5 to 10 parts by mass of water; (C) 0.1 to 20 parts by mass of a surfactant; and (D) an effective amount of a radical polymerization initiator. The curable composition is cured by polymerization in a state where a water layer is formed on the surfaces of the cured body that is being formed, effectively suppressing the hindrance of polymerization caused by oxygen and decreasing the formation of unpolymerized product on the surfaces of the cured body. The curable composition is particularly useful as a dental restorative.
Description
Technical field
The present invention relates to a kind of solidification compound, more particularly, the present invention relates to a kind of the grade oxygen barrier layer is set, just reduce the novel curable composition of the influence of oxygen when solidifying by the coating oxygen barrier material by radical polymerization formation cured article.
Background technology
Solidification compound as basal component, is the material that contains polymerisable monomer and polymerization starter.Solidification compound if carry out polymerization process in air, is exposed on the surface of airborne cured article and produces not polymeric layer when forming cured article by radical polymerization.This is that airborne oxygen combines with the polymerisable monomer of free radicalization and forms peroxide radical, thereby polymerization is stopped owing to being exposed on the surface of airborne solidification compound.
In the past, there is not the not cured article of polymeric layer from the teeth outwards in order to provide, carried out under nitrogen environment or in the water, solidifying, use oxygen barrier material that oxygen barrier layer etc. is set, cut off with the contacting of air in make solidification compound carry out the method for radical polymerization (for example, referring to patent documentation 1,2).
Patent documentation 1: the spy opens clear 2000-128723 communique
Patent documentation 2: the spy opens the 2004-284969 communique
Make (methyl) esters of acrylic acid polymerisable monomer solidified method by radical polymerization, be widely used for dental field, as the material that uses such method, can enumerate the finishing of dental cement, dental jointing material (matrix material), compound resin, the material of giving the resin dental material surface lubrication, tooth etc.In a single day these dental restorations have not polymeric layer on the cured article surface, just cause that surface hardness and tint permanence reduce.In addition since have not polymeric layer on the surface and when the polishing grinding that is cured thing not polymeric layer be wound on the polishing rod, cause its polishability to reduce.
Use as mentioned above the dental treatment great majority of dental repair materials directly solidify use in the oral cavity, since be in water or nitrogen environment under polymkeric substance is not reduced by curing method, therefore need earlier solidification compound to be taken out in the oral cavity, the shape that forms in the oral cavity so just has been out of shape.In addition, great majority are the trouble examples that be difficult to form oxygen barrier layer, and can not utilize oxygen barrier material on low material such as the viscosity of matrix material etc.
As mentioned above, the method for record is not suitable for the purposes of dental repair materials etc. in patent documentation 1,2, the technology that the influence of oxygen when solidifying is reduced.
On the other hand, reported by in the monomer of free redical polymerization, adding tensio-active agent, obtained the time as the binding agent of sclerous tissueses such as tooth, little and to the stimulation of dental pulp to the little solidification compound of soaking into of dentine (referring to patent documentation 3).
Patent documentation 3: the spy opens flat 7-316391 communique
But patent documentation 3 discloses as the further mixing water of diluting solvent, this diluting solvent can use when using tensio-active agent as bed material, for example, the bed material (monomer that contains free redical polymerization sometimes) that will contain water and tensio-active agent is applied on tooth etc., drying, coating contains the monomer of free redical polymerization and the composition of polymerization starter carries out polymerizing curable then.Therefore, do not have water in the patent documentation 3 when solidifying, water does not exert an influence to the formation of polymkeric substance not.
Summary of the invention
The purpose of this invention is to provide a kind ofly when under the environment of aerobic, being cured,, just suppress the not solidification compound of the formation of polymeric layer of surface effectively without oxygen barrier material by radical polymerization.
Other purpose of the present invention provides a kind of solidification compound that is applicable to effectively as the purposes of dental repair materials.
The inventor furthers investigate and has realized above-mentioned purpose.Found that, under the monomeric situation of using specific free redical polymerization,, can reduce the polymerization retardation effect of oxygen effectively, finished the present invention based on this new discovery by with less water and tensio-active agent and usefulness.
The invention provides a kind of solidification compound, comprising:
(A) form by the monomer of free redical polymerization and absorption of water is 20wt% or lower monomer component 100 mass parts;
(B) water 0.5~10 mass parts;
(C) tensio-active agent 0.1~20 mass parts; With
(D) radical polymerization initiator of significant quantity.
In the solidification compound of the present invention, preferred
(1) aforementioned monomer composition (A) is that absorption of water is that 5wt% or lower strong-hydrophobicity polymerisable monomer (a-1) and absorption of water are the mixture of 100wt% or higher strongly hydrophilic polymerisable monomer (a-2),
(2) aforementioned surfactants (C) is made up of anionic surfactant (c-1) and nonionic surfactant (c-2),
(3) the aforementioned monomer composition (A) of relative 100 mass parts contains the aforementioned anionic surfactant (c-1) of 0.1~10 mass parts and the aforementioned nonionic surfactant (c-2) of 0.1~10 mass parts,
(4) the aforementioned monomer composition (A) of relative 100 mass parts also contains the water-soluble polymers (E) of 0.00001~10 mass parts.
And in the present invention, the absorption of water of monomer component is to be calculated by the value substitution following formula of measuring the water content of the monomer component that the monomer by free redical polymerization of saturated suction forms by Karl Fischer method under 23 ℃.
The weight (g) * 100 of absorption of water=water content (g)/monomer component (A)
Contain above-mentioned (A)~(D) composition or further contain the solidification compound of the present invention of (E) composition, even when under the environment of aerobic, carrying out polymerizing curable, do not use special means such as oxygen barrier material, also can obtain with surface that oxygen contacts on the cured article that is inhibited effectively of the formation of polymeric layer not.This cured article, because the formation of polymeric layer is not inhibited, so excellents such as physical strength and weather resistance.For example, surperficial at least a portion of this solidification compound is under the situation that the environment that contains aerobic is opened, even when forming cured article by radical polymerization, on the cured article surface not the formation of polymeric layer suppressed effectively, the gained cured article, particularly resemble the excellent of the sort of dental repair materials of polishability requirement, this solidification compound is particularly exceedingly useful as the purposes of dental repair materials.
Embodiment
Solidification compound of the present invention, contain monomer component (A) and the polymerization starter (D) formed by the monomer of free redical polymerization, yet the feature of particularly important is optionally to use the monomer of specific free redical polymerization by absorption of water mode of (20wt% or lower) below certain value of monomer component (A), and with the monomer component of adjusting absorption of water in this way (A) combination, and water (composition B) and tensio-active agent (composition C).
Promptly, in this solidification compound, effect by polymerization starter makes monomer component (A) polymerization of being made up of the monomer of free redical polymerization form cured article, yet because polymerization is to carry out under the situation that water and tensio-active agent are arranged, form the layer of tensio-active agent and water on the surface at cured article when the monomer of free redical polymerization solidifies, the layer that this tensio-active agent and water form has stoped oxygen to the inner intrusion of cured article, and the result has reduced the not formation of polymkeric substance on the cured article surface.Therefore, on the cured article surface of following polymerization to produce, need have water and tensio-active agent with certain quality of balance, for example, under the too much situation of water or tensio-active agent, cured article intensity reduces, or can not solidify fully sometimes.Therefore, the present invention is adjusted to the absorption of water of monomer component (A) in the certain limit, and the amount of the water (composition B) of monomer component (A) and tensio-active agent (composition C) also must be set within the specific limits relatively.Each composition is described in detail in detail below.
<monomer component (A) 〉
In the present invention, become (A), can use the monomer of free redical polymerization as monomer, however this monomer component (A), and the absorption of water of measuring by preceding method is necessary for 20wt% or lower.And, as monomer component (A), absorption of water is that the monomer of 20wt% or lower free redical polymerization can a kind uses separately, perhaps can be the monomer and the usefulness of monomer and the absorption of water of 20wt% or the lower free redical polymerization free redical polymerization bigger with absorption of water, and absorption of water is adjusted to 20wt% or lower mixture uses as monomer component (A) than 20wt%.And, this monomer of the wetting ability free redical polymerization of absorption of water height (absorption of water is 100wt% or higher) when independent of weevil base Hydroxyethyl Acrylate also can be that the form of 20wt% or lower mixture is used as monomer component (A) with the combination of monomers of the low hydrophobicity free redical polymerization of absorption of water with the absorption of water.
That is, in the present invention, when the absorption of water of monomer component (A) is bigger than 20wt%, worry can not form water layer on the cured article surface that forms when carrying out polymerizing curable, the result can not reduce the not formation of polymkeric substance on the cured article surface.
In solidification compound of the present invention, suppress effect in order to improve on the cured article surface the not formation of polymkeric substance, obtain the more excellent cured article of mechanical characteristics, the absorption of water of above-mentioned monomer component (A) is more preferably 0.1~15wt%, most preferably in the scope of 0.5~5wt%.
As mentioned above, as long as absorption of water is adjusted in the above-mentioned scope, the monomer that can use various free redical polymerizations is as monomer component (A), however particularly from the polymerizability excellence, near room temperature also solidified angle easily, preferred (methyl) acrylic acid or the like polymerisable monomer that uses.(methyl) acrylic acid or the like polymerisable monomer like this according to its absorption of water, makes the absorption of water of monomer component (A) in above-mentioned scope, and they can use separately or two or more mix and use.
And, the absorption of water of monomer component (A) can obtain by Karl Fischer method as mentioned above, yet as simple target, the polymerisable monomer of 100 mass parts can be mixed with the water of 20 mass parts, can judge evenly whether absorption of water is 20wt% or lower according to whether becoming.That is, if become evenly, if absorption of water inhomogeneous, can judge that absorption of water is 20wt% or lower greater than 20wt% so.
Absorption of water is 20wt% or lower hydrophobicity (methyl) acrylic acid or the like polymerisable monomer when independent, can be listed below compound.Value in the bracket is an absorption of water, and the value of the absorption of water of band * is the value of being inferred by molecular structure.
The mean number of ethylene oxide group be 6 polyethoxylated trimethylolpropane trimethacrylate (
*5~10wt%)
The mean number of ethylene oxide group be 10 ethoxylation bisphenol a dimethacrylate (
*5~10wt%)
The mean number of ethylene oxide group be 13 ethoxylation bisphenol a dimethacrylate (
*10~20wt%)
The mean number of ethylene oxide group be 9 polyethoxylated trimethylolpropane trimethacrylate (
*10~20wt%)
Methacrylic acid hydroxyl pentyl ester (
*10~20wt%)
Methacrylic acid hydroxyl butyl ester (
*10~20wt%)
The glycerine dimethacrylate (
*10~20wt%)
Methyl methacrylate (1.5wt%)
Jia Jibingxisuanyizhi (1.0wt% or lower)
Methacrylic butyl ester (1.0wt% or lower)
Isopropyl methacrylate (1.0wt% or lower)
Acetoacetoxyethyl methacrylate (1.8wt%)
2,2-two (methacryloxy phenyl) propane (1.0wt% or lower)
2,2-two [4-(3-methacryloxy)-2-hydroxyl propoxy-phenyl] propane (2.2wt%)
2,2-two (4-methacryloxy phenyl) propane (0.5wt% or lower)
2,2-. two (4-methacryloxy polyethoxye phenyl) propane (0.5wt%)
2,2-two (4-methacryloxy diethoxy phenyl) propane (1.0% or lower)
2,2-two (4-methacryloxy tetraethoxy phenyl) propane (
*1~5%)
2,2-two (4-methacryloxy five ethoxyl phenenyls) propane (
*1~5%)
2,2-two or two (4-methacryloxy dipropoxy phenyl) propane (
*1~5%)
2 (4-methacryloxy diethoxy phenyl)-2 (4-methacryloxy diethoxy phenyl) propane (
*1~5%)
2 (4-methacryloxy diethoxy phenyl)-2 (4-methacryloxy two triethoxy phenyl) propane (
*1~5%)
2 (4-methacryloxy dipropoxy phenyl)-2-(4-methacryloxy triethoxy phenyl) propane (
*1~5%)
2,2-two (4-methacryloxy propoxy-phenyl) propane (
*1~5%)
2,2-two (4-methacryloxy isopropyl phenyl) propane (
*1~5%)
Monoethylene glycol dimethacrylate (1.0% or lower)
Diethylene glycol dimethacrylate (
*1~5%)
Triethylene glycol dimethacrylate (1.7%)
Tetraethylene glycol dimethacrylate (
*1~5%)
1,3 butylene glycol dimethacrylate (0.5% or lower)
1,4-butylene glycol dimethacrylate (0.5% or lower)
1,6-hexanediol dimethacrylate (0.1%)
1,9-nonanediol dimethacrylate (0.1%)
Trimethylolpropane trimethacrylate (
*1~5%)
The trimethylolethane trimethacrylate methacrylic ester (
*1~5%)
Pentaerythritol acrylate trimethyl (
*1~5%)
The Pehanorm trimethacrylate (
*1~5%)
Tetramethylolmethane tetramethyl-acrylate (
*1~5%) etc.
In the present invention, especially preferably use absorption of water to be 5wt% or lower strong-hydrophobicity (methyl) acrylic acid or the like polymerisable monomer (a-1) in the above-claimed cpd, that is, and following polymerisable monomer.
Strong-hydrophobicity (methyl) acrylic acid or the like polymerisable monomer (a-1):
2,2-two (methacryloxy phenyl) propane (0.5wt%)
2,2-two [4 (3-methacryloxy)-2-hydroxyl propoxy-phenyl] propane (2.2wt%)
2,2-two (4-methacryloxy phenyl) propane (1.0% or lower)
2,2-two (4-methacryloxy polyethoxye phenyl) propane (0.5%)
2,2-two (4-methacryloxy diethoxy phenyl) propane (1.0wt% or lower)
2,2-two (4-methacryloxy tetraethoxy phenyl) propane (
*1~5%)
2,2-two (4-methacryloxy five ethoxyl phenenyls) propane (
*1~5wt%)
2,2-two (4-methacryloxy dipropoxy phenyl) propane (
*1~5wt%)
2 (4-methacryloxy diethoxy phenyl)-2 (4-methacryloxy diethoxy phenyl) propane (
*1~5wt%)
2 (4-methacryloxy diethoxy phenyl)-2 (4-methacryloxy two triethoxy phenyl) propane (
*1~5wt%)
2 (4-methacryloxy dipropoxy phenyl)-2-(4-methacryloxy triethoxy phenyl) propane (
*1~5wt%)
2,2-two (4-methacryloxy propoxy-phenyl) propane (
*1~5wt%)
2,2-two (4-methacryloxy isopropyl phenyl) propane (
*1~5wt%)
1,3 butylene glycol dimethacrylate (0.5wt% or lower)
1,4-butylene glycol dimethacrylate (0.5wt% or lower)
1,6-hexanediol dimethacrylate (0.1wt%)
1,9-nonanediol dimethacrylate (0.1wt%)
Monoethylene glycol dimethacrylate (1.0wt% or lower)
Diethylene glycol dimethacrylate (
*1~5wt%)
Triethylene glycol dimethacrylate (1.7wt%)
Tetraethylene glycol dimethacrylate (
*1~5wt%).
And, (methyl) acrylic acid or the like polymerisable monomer that absorption of water is bigger than 20wt% can be various materials, yet in the present invention, selecting absorption of water especially is 100wt% or higher strongly hydrophilic (methyl) acrylic acid or the like polymerisable monomer (a-2), with itself and aforesaid absorption of water is 20wt% or lower hydrophobicity (methyl) acrylic acid or the like polymerisable monomer, particularly absorption of water is 5wt% or lower strong-hydrophobicity (methyl) acrylic acid or the like polymerisable monomer (a-1) combination, make that absorption of water is 20wt% or lower (preferred 0.1~15wt%, most preferably 0.5~5wt%), it is suitable using with the form of this mixture.The mode that the combination of monomers of the monomer of this hydrophobicity free redical polymerization and wetting ability free redical polymerization is used, make on the cured article surface that the inhibition effect of the formation of polymkeric substance does not improve, particularly strong-hydrophobicity (methyl) acrylic acid or the like polymerisable monomer and strongly hydrophilic (methyl) acrylic acid or the like polymerisable monomer combination, as shown in the embodiment of back, can significantly reduce the not formation of polymkeric substance.As this absorption of water is 100wt% or higher strongly hydrophilic (methyl) acrylic acid or the like polymerisable monomer (A-2), can enumerate following material.Below listed compound, all have strongly hydrophilic, can any amount soluble in water, absorption of water surpasses 100%.
Strongly hydrophilic (methyl) acrylic acid or the like polymerisable monomer (a-2):
Vinylformic acid
Methacrylic acid
(methyl) vinylformic acid 2-hydroxy methacrylate
(methyl) vinylformic acid 2-hydroxy propyl ester
(methyl) vinylformic acid 3-hydroxy propyl ester
(methyl) vinylformic acid 1,3-dihydroxyl propyl ester
(methyl) vinylformic acid 2,3-dihydroxyl propyl ester
(methyl) acrylamide
2-hydroxyethyl (methyl) acrylamide
Molecular-weight average is 400 or the dimethacrylate of bigger polyoxyethylene glycol
Molecular-weight average is 400 or the methacrylic ester of bigger polyoxyethylene glycol
Biphosphate 2-methacryloxy ethyl ester
The mean number of ethylene oxide group is 25 or bigger ethoxylation bisphenol a dimethacrylate.
And, in the present invention, in the monomer and the time spent of the monomer and the wetting ability free redical polymerization of this hydrophobicity free redical polymerization, although the reason of the reduction effect of the formation of polymkeric substance raising is also not indeterminate on the surface, but by containing the monomer of wetting ability free redical polymerization, relative solidification compound, the dispersiveness of water improves, and can predict it whether is because the homogeneity raising of the layer that the tensio-active agent that forms from the teeth outwards when this solidification compound is solidified and water constitute thus.
And, as mentioned above, with the monomeric mixture of two or more free redical polymerizations during as monomer component (A), the absorption of water of this mixture itself can be calculated by arithmetical mean by the monomeric absorption of water of each free redical polymerization, and it is just passable therefore according to their ratio of mixture of target adjusting the absorption of water of monomer component (A) to be adjusted in the aforementioned range.For example, the monomeric mixture that uses the monomer of strong-hydrophobicity free redical polymerization and strongly hydrophilic free redical polymerization for absorption of water is adjusted in the aforementioned range, can use the monomer of strong-hydrophobicity free redical polymerization during as monomer component (A) in a large number.
And, in the present invention, as long as (promptly with the absorption of water of monomer component (A), the absorption of water of the monomer integral body of used free redical polymerization) is adjusted in the aforementioned range, can with the monomer of various free redical polymerizations separately or two or more mix and use, particularly, by a large amount of use two senses or the monomer more than the trifunctional, can make mechanical properties such as the intensity of cured article of final gained and weather resistance all good.
In addition, in solidification compound of the present invention, except aforementioned (methyl) acrylic acid or the like polymerisable monomer, for easily polymerization, regulate viscosity or regulate other rerum natura, also can mix the monomer that uses other free redical polymerization except that above-mentioned (methyl) acrylic acid or the like polymerisable monomer.In either case, the absorption of water of the monomer component of free redical polymerization is necessary for 20wt% or lower.The monomeric example of these other free redical polymerization can have been enumerated vinylbenzene or alpha-methyl styrene derivatives such as fumaric acid esters, vinylbenzene, Vinylstyrene, alpha-methyl styrene such as monomethyl fumarate, DEF, fumaric acid diphenyl ester; Allylic cpds such as diallyl p phthalate, Phthalic acid, diallyl ester, diallyl diglycol carbonates etc.The monomer of these other free redical polymerizations can use separately, and perhaps two or more are also used.
<water (composition B) 〉
In solidification compound of the present invention, comprise in the matrix of aforementioned monomer composition (A) and be dispersed with water, under the state that is dispersed with water thus, be cured by radical polymerization, form cured article.Promptly, because water is carrying out radical polymerization under tensio-active agent dispersive state described later, therefore carrying out the polymeric suitable water layer (containing tensio-active agent) of formation on the cured article surface of formation simultaneously, this water layer suppresses oxygen invades in cured article, and the result can suppress to form on the cured article surface not polymkeric substance.
The aforementioned monomer composition (A) of relative 100 mass parts, the combined amount of this water are in 0.5~10 mass parts, and preferred 0.5~5 mass parts is most preferably in the scope of 1~3 mass parts.That is, the combined amount of water is many more, can reduce the not formation of polymkeric substance more, but the mechanical properties of cured articles such as opposite intensity and hardness has also reduced.And, when mixing water not and when in water, carrying out polymerizing curable, no problem from the angle that reduces the not formation of polymkeric substance, but the mechanical characteristics of cured article significantly reduces, or solidify not enough, solidification compound must be impregnated in the water, so the purposes of solidification compound obviously is restricted, for example can not be applicable to for example purposes such as dental repair materials.And, the present invention can aforesaid amount with water-dispersion in solidification compound.
<tensio-active agent (composition C) 〉
In solidification compound of the present invention, tensio-active agent and water are mixed together.That is, by using tensio-active agent, carry out polymeric simultaneously can be on the surface of the cured article that forms the branch water distribution layer, thereby can reduce the not formation of polymkeric substance on the cured article surface effectively.
The aforementioned monomer composition (A) of relative 100 mass parts, this tensio-active agent uses with the amount of 0.1~20 mass parts.That is, same with water, the combined amount of tensio-active agent is many more, can reduce the not formation of polymkeric substance on the surface more, but the mechanical characteristics of cured article has reduced but.Therefore, the combined amount of tensio-active agent is in above-mentioned scope.
And, as tensio-active agent, can use in anionic property, cationic, amphoteric plasma type tensio-active agent and the nonionic surfactant any one.The specific examples of such tensio-active agent has no particular limits, and can be following material:
The anionic surfactant:
Alkyl-sulphate such as sodium decyl sulfate, sodium lauryl sulphate;
Alkylsulfonates such as sodium hexanesulfonate, decyl sodium sulfonate;
Alkylbenzene sulfonates such as decyl benzene sulfonic acid sodium salt, Sodium dodecylbenzene sulfonate;
Aliphatic acid metallic salts such as sodium laurate, sodium stearate, sodium oleate;
The affixture of lauryl alcohol and ethylene oxide is through the metallic salt of senior alkyl ether sulphate such as Sulfated lauryl ether sodium sulfovinate;
Sulfosuccinic acid diesters classes such as sodium sulfosuccinate;
The phosphates of higher alcohols ethylene oxide adduct;
Cationic surfactant:
Alkylamine salts such as dodecyl chlorination ammonium;
Quaternary ammonium salts such as trimethyldodecane base brometo de amonio;
Zwitterionics:
Alkyl dimethyl amine oxide classes such as dimethyl dodecyl amine oxide;
Alkyl carboxyl betaines such as dodecyl carboxybetaine;
Alkyl sultaine classes such as dodecyl sultaine;
Amido amino acid saltss such as lauroyl amido propyl group amine oxide;
Nonionic surfactant:
Voranol EP 2001 classes such as polyoxyethylene lauryl ether;
Polyoxyethylene alkyl phenyl ether classes such as polyoxyethylene lauryl phenyl ether;
Polyoxyethylene carboxylate classes such as aliphatic acid polyethenoxy Lauryl Ester;
Sorbitan ethoxylate classes such as polyethenoxy sorbitan Lauryl Ester.
In the present invention, above-mentioned tensio-active agent, separately can a kind or two or more mix and use, but especially preferably anionic surfactant (C-1) can be mixed use with nonionic surfactant (c-2).That is, can know clearly that when by described 2 kinds of tensio-active agents and time spent being compared when using separately with tensio-active agent, the formation inhibition effect at the lip-deep not polymkeric substance of cured article during polymerizing curable significantly improves from aftermentioned embodiment.
And, mixed anionic surfactant's solidification compound, there is the low problem of package stability under the so-called low temperature.That is, the monomer of free redical polymerization and polymerization starter blended solidification compound have carried out polymerizing curable sometimes at lay up period, and therefore, (for example 0~10 ℃) is stored in refrigeration in advance, gets back to room temperature during use and carries out polymerizing curable.In this case, if the mixed anion surfacant, they are just separated out, and the result not formation of polymkeric substance suppresses the effect reduction.Yet, when as above-mentioned anionic surfactant (c-1) is mixed when use with nonionic surfactant (c-2), anionic surfactant in the time of can preventing from effectively to refrigerate storage separates out, and therefore can improve the preservation stability of solidification compound.
In anionic surfactant (c-1) and nonionic surfactant (c-2) and time spent, as the anionic surfactant (c-1) who uses, in aforementioned listed compound, the preferred HLB of the angle of the formation of polymkeric substance (hydrophilic-lipophilic balance) is 20~50 from suppressing on the surface not, particularly 30~50 compound most preferably uses alkyl-sulphate, alkylsulfonate, alkylbenzene sulfonate (wherein the carbonatoms of alkyl is 6~16).And as nonionic surfactant (c-2), in aforementioned listed compound, preferred HLB is 3 or higher, particularly 6~18 compound.And, with these tensio-active agents and time spent, the aforementioned monomer composition (A) of relative 100 mass parts, from the angle preferred anionic surfacant (C-1) of the formation that suppresses polymkeric substance not and package stability with 0.1~10 mass parts, particularly the amount of 0.3~3 mass parts is used, nonionic surfactant (c-2) is in 0.1~10 mass parts, particularly in the scope of 0.3~3 mass parts.
<polymerization starter (components D) 〉
Solidification compound of the present invention is mixed with the polymerization starter that is used for polymerization aforementioned monomer composition (A).As this polymerization starter, as long as monomer polymerization, the curing of the free redical polymerization that uses as monomer component (A) can be able to be used known polymerization starter without any restrictedly using.For example, polymerization starter as the dental field use, chemical polymerisation initiator (normal temperature oxidation reduction initiator), Photoepolymerizationinitiater initiater, thermal polymerization etc. are arranged, yet consider and in the oral cavity, solidify, preferred chemical polymerisation initiator and/or Photoepolymerizationinitiater initiater.Describe at various polymerization starters below.
-chemical polymerisation initiator-
Chemical polymerisation initiator is grouped into by two or more one-tenth, is before being about to use whole compositions to be mixed, and produces the polymerization starter of polymerization activity kind near room temperature.As such chemical polymerisation initiator, representational have amine compound/organic peroxide systems.
The example of the amine compound that uses as such chemical polymerisation initiator can have been enumerated N, N-dimethyl-para-totuidine, N, accelerine, N, aromatic amines compounds such as N-di-alcohol-para-totuidine.
And; the representative substances of the organo-peroxide that uses as chemical polymerisation initiator has ketone peroxide, peroxy ketal, hydroperoxide, diaryl superoxide, peroxy esters, diacyl peroxide, peroxy dicarbonate etc.; specifically, can enumerate following material.
Ketone peroxide:
Methyl-ethyl-ketone peroxide, pimelinketone superoxide, methyl cyclohexanone peroxide, methyl acetoacetate superoxide, acetylacetone peroxide etc.
Peroxy ketal:
1,1-two (uncle's hexyl peroxide) 3,3, the 5-trimethyl-cyclohexane,
1,1-two (uncle's hexyl peroxide) hexanaphthene,
1,1-two (t-butyl peroxy) 3,3, the 5-trimethylcyclohexanone,
1,1-two (t-butyl peroxy) hexanaphthene,
1,1-two (t-butyl peroxy) cyclodecane,
2,2-two (t-butyl peroxy) butane,
4,4 (two (t-butyl peroxy) n-butyl pentanoate,
2,2-two (4,4-di-t-butyl peroxide cyclohexyl) propane etc.
Hydroperoxide:
P-methane hydroperoxide,
The diisopropyl benzene superoxide,
1,1,3,3-tetramethyl butyl hydroperoxide,
Cumene hydroperoxide,
Uncle's hexyl hydroperoxide,
Tert-butyl hydroperoxide etc.
Dialkyl peroxide:
α, α-two (t-butyl peroxy) diisopropyl benzene,
Dicumyl peroxide,
2,5-dimethyl-2,5-two (t-butyl peroxy) hexane,
Tertiary butyl cumyl peroxide,
Ditertiary butyl peroxide,
2,5-dimethyl-2,5-two (t-butyl peroxy) hexane-3 etc.
Diacyl peroxide:
The isobutyryl superoxide,
2,4 dichloro benzene formyl radical superoxide,
3,5,5-trimethyl acetyl base superoxide,
Sim peroxides,
The lauroyl superoxide,
The stearyl-superoxide,
Succinic acid peroxide,
Toluoyl base benzoyl peroxide,
Benzoyl peroxide etc.
Peroxycarbonates:
Di n propyl peroxy dicarbonate,
Diisopropyl peroxydicarbonate,
Two (4-tert-butylcyclohexyl) peroxide, two carbonic ethers,
Two-2-ethoxyethyl group peroxide, two carbonic ethers,
Two-2-ethylhexyl peroxide, two carbonic ethers,
Two-2-methoxyl group butyl peroxy, two carbonic ethers,
Two (3-methyl-3-methoxyl group butyl) peroxide two carbonic ethers etc.
Peroxy esters:
α, α-two (new decanoyl peroxide) diisopropyl benzene,
Cumyl peroxide neodecanoic acid ester,
1,1,3,3-tetramethyl butyl peroxide neodecanoic acid ester,
1-cyclohexyl-1-methylethyl peroxide neodecanoic acid ester,
Uncle's hexyl peroxide neodecanoic acid ester,
T-butyl peroxy neodecanoic acid ester,
Uncle's hexyl peroxide pivalate,
The t-butyl peroxy pivalate,
1,1,3,3-tetramethyl butyl peroxide-2-ethylhexanoate,
2,5-dimethyl 2,5-two (2-ethyl hexanoyl base peroxide) hexane,
1-cyclohexyl-1-methylethyl peroxide-2-ethylhexanoate,
Uncle's hexyl peroxide-2-ethylhexanoate,
T-butyl peroxy-2-ethylhexanoate,
The t-butyl peroxy isobutyrate,
Uncle's hexyl peroxy isopropyl base monocarbonate,
The t-butyl peroxy toxilic acid,
T-butyl peroxy-3,5,5 Trimethylhexanoic acid ester,
The t-butyl peroxy laurate,
2,5-dimethyl-2,5-two (toluoyl base peroxide) hexane,
T-butyl peroxy sec.-propyl monocarbonate,
T-butyl peroxy-2-ethylhexyl monocarbonate,
Uncle's hexyl peroxy benzoate,
2,5-dimethyl-2,5-two (benzoyl peroxide) hexane,
The t-butyl peroxy acetic ester,
T-butyl peroxy toluoyl yl benzoic acid ester,
The t-butyl peroxy benzoic ether,
Two (t-butyl peroxy) isophthalic acid ester etc.
Other organo-peroxide:
Tertiary butyl trimethyl silyl superoxide,
3,3 ', 4,4 '-four (t-butyl peroxy carbonyl) benzophenone etc.
Used organo-peroxide can suitably be selected to use, and independent or two or more mixing are used all without any restriction, yet from the preferred especially hydroperoxide of the angle of polymerization activity, ketone peroxide, peroxy esters and diacyl peroxide.The angle of the package stability from as solidification compound the time, more preferably using 10 hours half life temperatures is 60 ℃ or higher organo-peroxide.
In the chemical polymerisation initiator that such organo-peroxide and amine compound are formed, can mix with benzene sulfinic acid or to barbital acids initiators such as-sulfinic acid such as toluenesulfinic acid and salt thereof or 5-butyl malonylureas further and use, without any problem.
And, utilize the aryl boric acid salt compound to decompose and produce free radical through acid, also can use the chemical polymerisation initiator of aryl boric acid salt compound/acidic cpd system.
The aryl boric acid salt compound, have no particular limits, so long as have the compound of at least one boron-aryl key in the molecule, can use known compound, wherein, consider package stability, preferably use the aryl boric acid salt compound that 3 or 4 boron-aryl keys are arranged in 1 molecule, from operating, synthesize, obtain the aryl boric acid salt compound that easy angle more preferably contains 4 boron-aryl key.As this aryl boric acid salt compound, can enumerate following material.
The borate compound that contains 3 boron-aryl key in 1 molecule:
As this aryl boric acid salt compound, can enumerate sodium salt, lithium salts, sylvite, magnesium salts, 4-butyl ammonium, tetramethyl ammonium, tetraethyl-ammonium salt, tributyl amine salt, triethanolamine salt, picoline salt, ethylpyridine salt, butyl-pyridinium salt, toluquinoline salt, ethyl quinoline salt or the butyl quinoline salt etc. of following boron compound.
The monoalkyl triphenyl-boron,
Monoalkyl three (right-chloro-phenyl-) boron,
Monoalkyl three (right-fluorophenyl) boron,
Monoalkyl three (3,5-two (trifluoromethyl)) phenyl boron,
Monoalkyl three [3,5-two (1,1,1,3,3,3-hexafluoro-2-methoxyl group-2-propyl group) phenyl] boron,
Monoalkyl three (right-nitrophenyl) boron,
Monoalkyl three (-nitrophenyl) boron,
Monoalkyl three (right-butyl phenyl) boron,
Monoalkyl three (-butyl phenyl) boron,
Monoalkyl three (right-butoxy phenyl) boron,
Monoalkyl three (-butoxy phenyl) boron,
Monoalkyl three (right-octyloxyphenyl) boron,
Monoalkyl three (-octyloxyphenyl) boron etc.
Wherein, in each compound in alkyl represent normal-butyl, n-octyl or the dodecyl any one.
The borate compound that contains 4 boron-aryl key in 1 molecule:
As this aryl boric acid salt compound, can enumerate sodium salt, lithium salts, sylvite, magnesium salts, 4-butyl ammonium, tetramethyl ammonium, tetraethyl-ammonium salt, tributyl amine salt, triethanolamine salt, picoline salt, ethylpyridine salt, butyl-pyridinium salt, toluquinoline salt, ethyl quinoline salt or the butyl quinoline salt etc. of following boron compound.
Tetraphenyl boron,
Four (right-chloro-phenyl-) boron,
Four (right-fluorophenyl) boron,
Four (3,5-two (trifluoromethyl)) phenyl boron,
Four [3,5-two (1,1,1,3,3,3-hexafluoro-2-methoxyl group-2-propyl group) phenyl] boron,
Four (right-nitrophenyl) boron,
Four (-nitrophenyl) boron,
Four (right-butyl phenyl) boron,
Four (-butyl phenyl) boron,
Four (right-butoxy phenyl) boron,
Four (-butoxy phenyl) boron,
Four (right-Xin oxygen phenyl) boron,
Four (-octyloxyphenyl) boron etc.
Wherein, in each compound in alkyl represent normal-butyl, n-octyl or the dodecyl any one.
Above-named various aryl boric acid salt compound also can two or more mix use.
And, as with the acidic cpd of above-mentioned aryl boric acid salt compound and usefulness, preferably can use the monomer of the free redical polymerization that contains acidic-group.The monomer of the free redical polymerization that uses as this acidic cpd contains in 1 molecule in free-radical polymerised unsaturated group and the acidic-group separately that at least one is just passable.This acidic-group works the monomeric aqueous solution or the aqeous suspension that make free redical polymerization and is the tart effect, can enumerate carboxyl (OOH), sulfo group (SO
3H), phosphinico-{=P (=O) OH}, phosphono { P (=O) (OH)
2Etc..And this acidic-group also can be present in the molecule with the form of 2 acidic-groups through the acid anhydride structure of dehydrating condensation, and the hydroxyl that perhaps also can be used as acidic-group is present in the molecule by the acyl halide group that halogen replaces.
As the monomer of the free redical polymerization that contains acidic-group as mentioned above, the monomer of the free redical polymerization of (methyl) acrylic acid or the like that preferred monomers composition (A) item is enumerated.
And, when the monomer of this free redical polymerization that contains acidic-group and aromatic yl acid salt compound are used as polymerization starter, this monomer that contains the free redical polymerization of acidic-group, owing to be included in the monomer component (A), therefore under the monomeric form that comprises this free redical polymerization that contains acidic-group, the absorption of water of monomer component (A) must be adjusted in the aforementioned range.
The polymerization starter of above-mentioned aryl boric acid salt compound/acidic cpd system can also be used in combination organo-peroxide and/or transistion metal compound.This organo-peroxide as previously mentioned.And, as transistion metal compound, preferred+IV valency or+vanadium compound of V valency.Specific examples as this vanadium compound, can enumerate vanadium tetraoxide (IV), etheric acid vanadium oxide (IV), vanadium oxalate (IV), Vanadosulfuric acid (IV), oxygenate two (1-phenyl 1,3-butanone acid group closes) vanadium (IV), two (voitol closes) vanadium oxide (IV), vanadium pentoxide (V), sodium metavanadate (V), ammonium meta-vanadate (V) etc.
-Photoepolymerizationinitiater initiater-
As Photoepolymerizationinitiater initiater, can use following material separately, perhaps two or more are mixed and use.
The acylphosphine oxide derivative:
2,4,6-trimethylbenzoyl diphenyl phosphine oxide,
2,6-dimethoxy benzoyl diphenyl phosphine oxide,
2,6-dichloro-benzoyl base diphenyl phosphine oxide,
2,4,6-trimethylbenzoyl phenyl-phosphonic acid methyl esters,
2-methyl benzoyl diphenyl phosphine oxide,
Valeryl phenyl-phosphonic acid isopropyl ester,
Two-(2,6-dichloro-benzoyl base) phenyl phosphine oxides,
Two-(2,6-dichloro-benzoyl base)-2,5-3,5-dimethylphenyl phosphine oxide,
Two-(2,6-dichloro-benzoyl base)-4-propyl group phenyl phosphine oxide,
Two-(2,6-dichloro-benzoyl base)-1-naphthyl phosphine oxide,
Two-(2,6-dimethoxy benzoyl) phenyl phosphine oxides,
Two-(2,6-dimethoxy benzoyl)-2,4,4-tri-methyl-amyl phosphine oxide,
Two-(2,6-dimethoxy benzoyl)-2,5-3,5-dimethylphenyl phosphine oxide,
Two-(2,4, the 6-trimethylbenzoyl) phenyl phosphine oxides,
Two-(2,5, the 6-trimethylbenzoyl)-2,4,4-tri-methyl-amyl phosphine oxide etc.
α-diketone:
Dimethyl diketone,
Methylphenyl diketone,
Benzil,
2, the 3-diacetylmethane,
2, the 3-acetyl caproyl,
4,4 '-the dimethoxy benzil,
4,4 '-the hydroxyl benzil,
Camphanone,
9, the 10-phenanthrenequione,
Acenaphthene quinone etc.
Benzoin alkylether:
Benzoin methylether,
Ethoxybenzoin,
Bitter almond oil camphor propyl ether etc.
Thioxanthone derivates:
2,4-diethoxy thioxanthone,
The 2-clopenthixal ketone,
Methyl thioxanthone etc.
Benzophenone derivates:
Benzophenone,
P, p '-dimethylamino benzophenone,
P, p '-methoxy benzophenone etc.
In the above-mentioned Photoepolymerizationinitiater initiater, good from polymerization activity, to the little equal angles of the harm of organism preferred α-two ketone.And under the situation of using α-diketone, preferably mix use with tertiary amine compound.Can mix the tertiary amine compound that uses with α-diketone can be the material of enumerating below.
Tertiary amine compound:
N, accelerine,
N, the N-Diethyl Aniline,
N, N-di-n-butyl aniline,
N, the N-dibenzyl aniline,
N, N-dimethyl-para-totuidine,
N, N diethyl-para-totuidine,
N, N-dimethyl meta-aminotoluene,
Right-bromo-N, accelerine,
Between-chloro-N, accelerine,
Right-the dimethylamino benzaldehyde,
Right-the dimethylamino benzoylformaldoxime,
Right-the dimethylamino M-nitro benzoic acid,
Right-the dimethylamino ethyl benzoate,
Right-dimethylamino M-nitro benzoic acid pentyl ester,
N, N dimethyl methyl o-aminobenzoate,
N, N-dihydroxy ethyl aniline,
N, N-dihydroxy ethyl-para-totuidine,
Right-the dimethylamino phenylethyl alcohol,
Right-the dimethylamino Stilbene,
N, N-dimethyl-3, the 5-xylidine,
4-dimethylaminopyridine,
N, the N-dimethyl-,
N, N-dimethyl-beta-naphthylamine,
Tributylamine,
Tripropylamine,
Triethylamine,
N methyldiethanol amine,
The N-ethyldiethanolamine,
N, the N-dimethylhexylamine,
N, N-dimethyl lauryl amine,
N, N-dimethyl stearylamine,
Methacrylic acid N, the N-dimethylamino ethyl ester,
Methacrylic acid N, N-diethylamino ethyl ester,
2,2 '-(normal-butyl imino-) di-alcohol etc.
Above-mentioned various polymerization starter not only can use separately separately, and can multiple mixing use as required.
In the present invention, the combined amount of these polymerization starters, so long as can be with the amount of monomer component (A) polymerizing curable formed by the monomer of aforementioned free redical polymerization, this is had no particular limits, according to the kind of used polymerization starter and the composition of monomer component (A), suitably select known combined amount just passable.In general, the monomer component of relative 100 mass parts (A), this amount is 0.01~30 mass parts, particularly 0.1~5 mass parts.But, as the aforementioned monomer that contains the free redical polymerization of acidic-group, under the situation of free-radical polymerised compound as a kind of composition use of polymerization starter, because monomer component (A) comprises this compound, therefore make the amount of the polymerization starter composition except that this compound in above-mentioned scope.
<water-soluble polymers (composition E) 〉
And, in the present invention, except above-mentioned (A)~(D) composition, can the mixing water soluble polymer, can reduce the not formation of polymkeric substance on the cured article surface thus greatly.That is, water-soluble polymers, water-soluble, with tensio-active agent, be distributed in the water layer that on the cured article surface, forms.Therefore, think the oxygen barrier performance that can improve water layer, the formation of polymkeric substance suppresses effect and does not significantly improve.
And the water-soluble polymers among the present invention is meant that the solubleness to water is 1g/l or higher polymkeric substance under 23 ℃.
As the example of this water-soluble polymers, can enumerate multipolymer, vinyl-acetic ester-acrylic copolymer, vinyl-acetic ester-ethylene copolymer, vinylformic acid-styrol copolymer, ammonia esters resin vinylidene resin of polyvinyl alcohol, Polyvinylpyrolidone (PVP), polyoxyethylene, derivatived cellulose, polyacrylic acid, polymethyl acrylic acid, sodium polyacrylate, sodium polymethacrylate, gelatin, alkyl vinyl ether and maleic anhydride etc.Wherein, the angle of the influence of oxygen is especially preferably used polyvinyl alcohol, polyacrylic acid etc. when further reduction is solidified.These water-soluble polymerss can use separately, perhaps can two or more also use.
And, above-mentioned water-soluble polymers, as long as to the solubleness of water in above-mentioned scope, this polymkeric substance is had no particular limits, yet if molecular weight is too big, it is too high that the viscosity of solidification compound becomes, this moment, operability reduced.Therefore, be preferably 1000~10,000,000, particularly 3000~500,000 with the weight-average molecular weight of polystyrene conversion.
In the present invention, the monomer component of relative 100 mass parts (A), the combined amount of above-mentioned water-soluble polymers can be in the scope of 0.00001~10 mass parts, preferred especially 0.0001~1 mass parts, most preferably 0.0005~0.5 mass parts.Combined amount is big more, can reduce the not formation of polymeric layer of surface, but combined amount is hour also little to the influence of rerum natura on the other hand.
<other mixing element 〉
Solidification compound of the present invention, itself can be as dental repair materials such as the surface lubrication material of giving purpose uses such as the surface lubrication of various resene dental material, tooth finishing and the reparation of variable color tooth and matrix materials, but by with filler combination, can be used for purposes widely.For example, with the situation of organic filler combination under, be suitable as artificial tooth repair materials, backing layer with being filled into interim closed material and interim artificial corona and bridge making material etc. the cavity in several days of begin treatment again from the patient back of going home in material, the therapeutic process.And, with the situation of mineral filler combination under, can suitably be used as dental repair materials such as compound resin, hard resin, inlay, onlay, artificial corona.
As can suitably used representational organic filler and mineral filler, can enumerate following material, they can any one independent use, also can two or more mix and use.
Organic filler:
Polymethylmethacrylate, polyethyl methacrylate, methyl methacrylate-ethyl methacrylate copolymers, cross-linking type polymethylmethacrylate, cross-linking type polyethyl methacrylate, vinyl-vinyl acetate copolymer, styrene-butadiene copolymer, acrylonitritrile-styrene resin, acrylonitrile-styrene-butadienecopolymer etc.
Mineral filler:
Quartz, silicon-dioxide, aluminum oxide, silicon oxide titanium, silicon oxide zirconium, lanthanum glass, barium glass, strontium glass etc.
And, in mineral filler, except above-mentioned enumerate, also have positively charged ion stripping property materials such as oxide compound such as oxyhydroxide, zinc oxide, silicate glass, aluminum fluoride glass such as calcium hydroxide, strontium hydroxide, these materials also can one or more mix and use.In addition, also have polymerisable monomer is added in the above-mentioned mineral filler in advance, behind the one-tenth pasty state,, pulverize the granular organic and inorganic compounded mix that obtains, also can use this organic and inorganic compounded mix through polymerization.
The particle diameter of above-mentioned various fillers has no particular limits, but the preferred scope of using as the median size (0.01 μ m~100 μ m) of the general filler that uses of dental material.And the specific refractory power of filler has no particular limits, 1.4~1.7 the scope that can use ad lib that the filler of general dental has.
Therefore in addition, cooperated in the above-mentioned filler the particularly solidification compound of spherical mineral filler, owing to the surface lubrication raising of gained cured article can become excellent dental repair materials.
And, above-mentioned mineral filler, through being that the surface treatment agent of representative is handled with the silane coupling agent,, physical strength good with the avidity of polymerisable monomer and water tolerance improve, and are preferred therefore.The surface-treated method can known method be carried out, and for example can carry out surface treatment by silane coupling agents such as methyltrimethoxy silane, Union carbide A-162, METHYL TRICHLORO SILANE, dimethyldichlorosilane(DMCS), trimethylchlorosilane, vinyl trichloro silane, vinyltriethoxysilane, vinyl three ('beta '-methoxy oxyethyl group) silane, γ-methacryloxypropyl trimethoxy silane, γ-r-chloropropyl trimethoxyl silane, γ-glycidoxypropyltrime,hoxysilane, hexamethyldisilazanes.
The combined amount of above-mentioned various fillers, can be according to application target, the mechanical properties of viscosity (operability) when consideration mixes with polymerisable monomer and the cured article that obtains suitably determines, in general, the monomer component of relative 100 mass parts (A), preferred 50~1500 mass parts are particularly in the scope of 70~1000 mass parts.
Solidification compound of the present invention, except above-mentioned filler, for example for consistent with the tone of tooth and gum, also can hybrid pigment, painted material such as high-visibility pigment, or add and be used to prevent ultraviolet ray relatively and the UV light absorber of variable color.And, in order to improve package stability, can mix stopper.
<solidification compound 〉
Solidification compound of the present invention, be with above-mentioned various composition uniform mixing, by with (B)~(D) composition and blended composition (E) water-soluble polymers and other any composition as required, be distributed to preparation in the monomer component (A), type according to the polymerization starter (D) that uses suitably heats, perhaps, form cured article through polymerizing curable by rayed.
And, consider the stability when storing, refrigeration is stored under the temperature about 0~10 ℃, can return to room temperature during use and carry out polymerizing curable.Particularly as tensio-active agent (C), solidification compound with anionic surfactant (c-1) and nonionic surfactant (c-2) combined hybrid, as mentioned above, because it is good that property is stored in refrigeration, therefore can avoid effectively waiting the performance reduction that causes because of the anionic surfactant separates out.
In addition, can be before be about to using with solidification compound with two or more composition separate storage, when storing, be not cured like this, all the components is mixed carry out polymerizing curable in use.
And, because polymerizing curable is to carry out under the state that aforementioned composition (B) water is arranged, even at least a portion surface is when carrying out polymerizing curable under atmosphere (oxygen atmosphere) opened state, therefore can suppress the not formation of polymkeric substance on the cured article surface effectively, can avoid effectively that polymkeric substance reduces hardness and intensity because of forming not.Therefore, solidification compound of the present invention, very useful aspect the purposes of dental repair materials, be not limited to dental use, and can be used for general industry.
Embodiment
Enumerate embodiment below and specifically describe the present invention, but in any case the present invention is not limited to these embodiment.
And, show the evaluation method of the solidification compound of the compound that uses in embodiment and the Comparative Examples and abbreviation and preparation below.
[monomer of free redical polymerization]
AAEM:
Acetoacetoxy groups ethyl-methyl acrylate (absorption of water: 1.4wt%)
HD:
1,6-hexanediol dimethacrylate (absorption of water: 0.1wt%)
bis-GMA:
2,2-two (4-(2-hydroxy-3-methyl acryloxy propoxy-) phenyl) propane (absorption of water: 2.2wt%)
3G:
Triethylene glycol dimethacrylate (absorption of water: 1.7wt%)
D2.6E:
2,2-two (4-methacryloxy polyethoxye phenyl) propane (absorption of water: 0.3wt%)
HEMA:
Methacrylic acid hydroxyl ethyl ester (absorption of water>100wt%)
14G:
Molecular weight is the dimethacrylate (absorption of water>100wt%) of 600 polyoxyethylene glycol
MAC-10:
11-methacryloxy-1,1-11 carbon dicarboxylic acid (absorptions of water: 0.6wt%)
PM:
The mixture of biphosphate 2-methacryloxy ethyl ester and phosphoric acid hydrogen two (2-methacryloxyethyl) ester (absorption of water>100wt%)
[anionic surfactant]
SLS:
Sodium lauryl sulphate (HLB:40)
SDS:
Sodium decyl sulfate (HLB:41)
SOS:
Hot sodium sulfonate
LBS:
Sodium dodecylbenzene sulfonate
[cationic surfactant]
LDAGCI:
DAG (HLB:30)
LTMACI:
Dodecyl trimethyl ammonium chloride (HLB:11)
[nonionic surfactant]
POEL:
Polyoxyethylene (10) lauryl ether (HLB:14)
POEL4:
Polyoxyethylene (4) lauryl ether (HLB:10)
POEO2:
Polyoxyethylene (2) oleyl ether (HLB:8)
POEO7:
Polyoxyethylene (7) oleyl ether (HLB:11)
POEO15:
Polyoxyethylene (15) oleyl ether (HLB:16)
[polymerization starter]
(organo-peroxide)
BPO:
Benzoyl peroxide
バ—オクH:
1,1,3,3-tetramethyl butyl hydroperoxide
(amine compound)
DEPT:
N, N-di-alcohol-para-totuidine
DMPT:
N, N-dimethyl-para-totuidine
PEAT:
N, N-diethyl-para-totuidine
DMBE:
The dimethyl ethyl benzoate
(α-diketone)
CQ: camphorquinone
(aryl boric acid salt compound)
PhBTEOA:
Tetraphenyl boron triethanolamine salt
(vanadium compound)
VOAA:
The ethanoyl acetate moiety closes vanadium oxide (IV)
[water-soluble polymers]
PVA1000:
Polyvinyl alcohol
(fully saponified thing, mean polymerisation degree 1000, molecular-weight average 50000)
[filler]
3Si-Zr:
Soft silica-zirconium white, γ-methacryloxypropyl trimethoxy silane surface treatment thing (median size: 3 μ m)
0.3Si-Ti:
The γ of spherical silicon dioxide-titanium oxide-methacryloxypropyl trimethoxy silane surface treatment thing (median size: 0.3 μ m)
PEMA:
Polyethyl methacrylate (median size: 30 μ m)
[absorption of water measuring method]
Monomer (or its mixture) with free redical polymerization under 23 ℃ mixes with water, measures this monomeric water content of saturated suction, obtains absorption of water according to following formula by カ-Le Off イ Star シ ャ-(CA-02 type, Mitsubishi Chemical society makes).
The weight (g) * 100 of absorption of water (%)=water content (g)/monomer (or its mixture)
[surface is the polymerization amount measuring method not]
In the model that the polyacetal in the hole with diameter 50mm, thick 1mm is made, fill the solidification compound for preparing in each embodiment or the Comparative Examples, under 37 ℃, wet condition, in thermostat container, place and be cured in 15 minutes.But embodiment 19~23 and Comparative Examples 16~20 are by being cured for 30 seconds with visible rays irradiator (ト Network ヤ マ society makes, パ ワ-ラ イ ト) rayed.
Afterwards, with ethanol surperficial the cleaning of gained cured article removed not polymeric layer.By the weight of the solidification compound of filling in the model, deduct and remove value that the weight of the cured article of polymeric layer not obtains as polymerization amount not, be expressed as the weight of per surface area.
[measuring method of flexural strength]
In the model that the polyacetal of the slot with wide 4mm, thick 2mm, long 40mm is made, fill solidification compound, to be cured in the same manner with the mensuration of polymerization amount not.
To the gained cured article, with strength testing machine (society of Shimadzu Seisakusho Ltd. makes, オ-ト グ ラ Off), under the condition of pinblock speed 1mm/ branch, span 15mm, carry out 3 pliability tests, obtain flexural strength.
And, according to the surface hardness of ADAS No.17 (Denture Base Temporary Relining Resins) mensuration cured article.
[evaluation of polishing grindability]
In the model that the polyacetal of the square hole with wide 10mm, thick 2mm is made, fill solidification compound, to be cured in the same manner with the mensuration of polymerization amount not.
Go up the installation skilled worker with カ-バ イ ト バ-(ト Network ヤ マ society makes, Ha-デ イ ア-ロ イ バ-DD6), estimate the polishing grindability on gained cured article surface the skilled worker with motor (モ リ society makes, micromotor ANS3000).Judgement criteria is as follows.
Zero: at the power-バ イ ト バ-not polymeric layer of upward not reeling
*: カ-バ イ ト バ-on be wound with not polymeric layer
[storage stability test]
Solidification compound stored for 1 week in 4 ℃ refrigerator after, separating out of look-up table surface-active agent estimated with two following standards.
Zero: do not have tensio-active agent to separate out
*: there is tensio-active agent to separate out
<embodiment 1 〉
Use absorption of water as the 3G of 1.7wt% as polymerisable monomer, according to following formulation first liquid and second liquid.
The prescription of first liquid:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (anionic surfactant): 1.5 mass parts
BPO (organo-peroxide): 3 mass parts
The prescription of second liquid:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (anionic surfactant): 1.5 mass parts
DMPT (amine compound): 1.5 mass parts
First liquid and second liquid that will have aforesaid composition mix, and prepare the solidification compound of following composition.
The composition of solidification compound:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (tensio-active agent): 1.5 mass parts
BPO (organo-peroxide): 1.5 mass parts
DMPT (amine compound): 0.75 mass parts
Estimate the various characteristics of this solidification compound according to foregoing method.Consequently the surface not polymerization amount be 6 μ g/mm
2, the flexural strength of cured article is 80MPa.
<embodiment 2~5 〉
Except the variation of the type of the tensio-active agent that uses such as table 1 record, prepare solidification compound in the same manner with embodiment 1, carry out the not evaluation of polymerization amount of surface.Show the result in table 1 with embodiment 1.
<Comparative Examples 1 〉
Except water, tensio-active agent do not use, prepare the solidification compound of forming shown in the table 1 with embodiment 1 identically.Consequently the surface not polymerization amount be 730 μ g/mm
2, and the flexural strength of cured article is 83MPa.
<Comparative Examples 2,3 〉
Prepare the solidification compound of forming shown in the table 1 in the same manner with embodiment 1, measure not polymerization amount of surface, it the results are shown in table 1.
[table 1]
Polymerisable monomer *Monomer component (A) | Water | Tensio-active agent | Polymerization starter | The surface is polymerization amount μ g/mm not 2 | |||
Type | Combined amount (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | ||
Embodiment 1 | 3G | 100 | 3 | SLS | 1.5 | 1.5/0.75 | 6 |
Embodiment 2 | 3G | 100 | 3 | SDS | 1.5 | 1.5/0.75 | 5 |
Embodiment 3 | 3G | 100 | 3 | LDAGCI | 1.5 | 1.5/0.75 | 18 |
Embodiment 4 | 3G | 100 | 3 | LTMACI | 1.5 | 1.5/0.75 | 58 |
Embodiment 5 | 3G | 100 | 3 | POEL | 1.5 | 1.5/0.75 | 56 |
Comparative Examples 1 | 3G | 100 | - | - | - | 1.5/0.75 | 730 |
Comparative Examples 2 | 3G | 100 | 3 | - | - | 1.5/0.75 | 580 |
Comparative Examples 3 | 3G | 100 | - | SLS | 1.5 | 1.5/0.75 | 730 |
*: the absorption of water of 3G is 1.7wt%
<embodiment 6 〉
Except use absorption of water be the HD of 0.1wt% as the polymerisable monomer, prepare the solidification compound of forming shown in the table 2 in the same manner with embodiment 1, measure not polymerization amount of surface.Consequently the surface not polymerization amount be 7 μ g/mm
2(the surface not measurement result of polymerization amount is presented at table 2 together.)
<Comparative Examples 4 〉
Except not mixing water and tensio-active agent, prepare the solidification compound of forming shown in the table 2 in the same manner with embodiment 6, carry out the not mensuration of polymerization amount of surface.Consequently the surface not polymerization amount be 512 μ g/mm
2(the surface not measurement result of polymerization amount is presented at table 2 together.)
<embodiment 7 〉
Except use absorption of water be the AAEM of 1.4wt% as the polymerisable monomer, prepare solidification compound in the same manner with embodiment 1, carry out the not mensuration of polymerization amount of surface.Consequently the surface not polymerization amount be 32 μ g/mm
2(the surface not measurement result of polymerization amount is presented at table 2 together.)
<embodiment 8 〉
The mixture of HEMA for preparing the AAEM of 95 mass parts and 5 mass parts is as polymerisable monomer.The absorption of water of measuring this polymerizable monomer mixture is 2.9wt%.
Except using said mixture to replace preparing solidification compound in the same manner with embodiment 1 3G, carry out the not mensuration of polymerization amount of surface.
Consequently the surface not polymerization amount be 6 μ g/mm
2(the surface not measurement result of polymerization amount is presented at table 2 together.)
<Comparative Examples 5 〉
Except not mixing water and tensio-active agent, with embodiment 7 in the same manner, use AAEM to prepare the solidification compound of forming shown in the table 2 as polymerisable monomer, carry out the not mensuration of polymerization amount of surface.Consequently the surface not polymerization amount be 652 μ g/mm
2(the surface not measurement result of polymerization amount is presented at table 2 together.)
<embodiment 9~11, Comparative Examples 6~9 〉
Use the polymerizable monomer mixture of AAEM and HEMA, with embodiment 1 in the same manner, the solidification compound of forming shown in the preparation table 2 carries out the not mensuration of polymerization amount of surface.With the absorption of water of the polymerizable monomer mixture that uses and surface not the evaluation result of polymerization amount be shown in table 2 together.
[table 2]
Polymerisable monomer (monomer component A) | Water | Tensio-active agent | Polymerization starter | The surface is polymerization amount not | ||||
Type | Combined amount absorption of water (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | |||
Embodiment 6 | HD | 100 | 0.1wt% | 3 | SLS | 1.5 | 1.5/0.75 | 7μg/mm 2 |
Embodiment 7 | AAEM | 100 | 1.4wt% | 3 | SLS | 1.5 | 1.5/0.75 | 32μg/mm 2 |
HEMA | - | |||||||
Embodiment 8 | AAEM | 95 | 2.9wt% | 3 | SLS | 1.5 | 1.5/0.75 | 6μg/mm 2 |
HEMA | 5 | |||||||
Embodiment 9 | AAEM | 70 | 10.3wt% | 3 | SLS | 1.5 | 1.5/0.75 | 12μg/mm 2 |
HEMA | 30 | |||||||
Embodiment 10 | AAEM | 50 | 16.4wt% | 3 | SLS | 1.5 | 1.5/0.75 | 52μg/mm 2 |
HEMA | 50 | |||||||
Embodiment 11 | AAEM | 50 | 16.4wt% | 5 | SLS | 1.5 | 1.5/0.75 | 8μg/mm 2 |
HEMA | 50 | |||||||
Comparative Examples 4 | HD | 100 | 0.1wt% | - | - | - | 1.5/0.75 | 512μg/mm 2 |
Comparative Examples 5 | AAEM | 100 | 1.4wt% | - | - | - | 1.5/0.75 | 652μg/mm 2 |
HEMA | - | |||||||
Comparative Examples 6 | AAEM | 95 | 2.9wt% | - | - | - | 1.5/0.75 | 644μg/mm 2 |
HEMA | 5 | |||||||
Comparative Examples 7 | AAEM | 70 | 10.3wt% | - | - | - | 1.5/0.75 | 638μg/mm 2 |
HEMA | 30 | |||||||
Comparative Examples 8 | AAEM | 50 | 16.4wt% | - | - | - | 1.5/0.75 | 562μg/mm 2 |
HEMA | 50 | |||||||
Comparative Examples 9 | AAEM | 20 | 28.3wt% | 3 | SLS | 1.5 | 1.5/0.75 | 521μg/mm 2 |
HEMA | 80 |
<embodiment 12~15, Comparative Examples 10~11 〉
Except the combined amount that changes water, tensio-active agent, with embodiment 1 in the same manner, the solidification compound of forming shown in the preparation table 3 carries out the not evaluation of polymerization amount and flexural strength of surface.The result is shown in table 3 with the result of the foregoing description 1.
[table 3]
Polymerisable monomer * | Water | Tensio-active agent | Polymerization starter | The surface is polymerization amount not | Flexural strength | |||
Type | Combined amount (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | |||
Embodiment 1 | 3G | 100 | 3 | SLS | 1.5 | 1.5/0.75 | 6μg/mm 2 | 80MPa |
Embodiment 12 | 3G | 100 | 1 | SLS | 1.5 | 1.5/0.75 | 38μg/mm 2 | 82MPa |
Embodiment 13 | 3G | 100 | 5 | SLS | 1.5 | 1.5/0.75 | 4μg/mm 2 | 76MPa |
Embodiment 14 | 3G | 100 | 3 | SLS | 1 | 1.5/0.75 | 9μg/mm 2 | 79MPa |
Embodiment 15 | 3G | 100 | 3 | SLS | 2 | 1.5/0.75 | 5μg/mm 2 | 79MPa |
Comparative Examples 10 | 3G | 100 | 0.1 | SLS | 1.5 | 1.5/0.75 | 630 μg/mm 2 | 83MPa |
Comparative Examples 11 | 3G | 100 | 20 | SLS | 1.5 | 1.5/0.75 | 52μg/mm 2 | 39MPa |
*: the absorption of water of 3G is 1.7wt%
<embodiment 16~18, Comparative Examples 12~15 〉
Except using the monomer mixture of forming shown in the table 4, and change outside the combined amount of water, tensio-active agent, with embodiment 1 in the same manner, the solidification compound of forming shown in the preparation table 4 carries out the not mensuration of polymerization amount and flexural strength of surface.The result is shown in table 3 with the result of described embodiment 1.
Except in order to reach the composition shown in the table 4, and change outside the combined amount of water, tensio-active agent, with embodiment 1 in the same manner, the preparation cured article is also estimated.With the surface not the evaluation result of polymerization amount be shown in table 4 with the result of previous embodiment 1.And, the absorption of water of the monomer mixture that uses is shown in table 4.
[table 4]
Polymerisable monomer (monomer component A) | Water | Tensio-active agent | Polymerization starter | The surface is polymerization amount not | ||||
Type | Combined amount absorption of water (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | |||
Embodiment 1 | 3G | 100 | 1.7wt% | 3 | SLS | 1.5 | 1.5/0.75 | 6μg/mm 2 |
Embodiment 16 | 3G | 90 | 2.4wt% | 3 | SLS | 1.5 | 1.5/0.75 | 1μg/mm 2 |
14G | 10 | |||||||
Embodiment 17 | 3G | 70 | 5.3wt% | 3 | SLS | 1.5 | 1.5/0.75 | 2μg/mm 2 |
14G | 30 | |||||||
Embodiment 18 | 3G | 95 | 2.9wt% | 3 | SLS | 1.5 | 1.5/0.75 | 2μg/mm 2 |
HEMA | 5 | |||||||
Comparative Examples 12 | 3G | 99.9 | 1.8wt% | 3 | SLS | 1.5 | 1.5/0.75 | 6μg/mm 2 |
14G | 0.1 | |||||||
Comparative Examples 13 | 3G | 30 | 23.2wt% | 3 | SLS | 1.5 | 1.5/0.75 | 612μg/mm 2 |
14G | 70 | |||||||
Comparative Examples 14 | 3G | 99.9 | 1.8wt% | 3 | SLS | 1.5 | 1.5/0.75 | 6μg/mm 2 |
HEMA | 0.1 | |||||||
Comparative Examples 15 | 3G | 30 | 25.3wt% | 3 | SLS | 1.5 | 1.5/0.75 | 566μg/mm 2 |
HEMA | 70 |
<embodiment 19~20, Comparative Examples 16~17 〉
Under the shading, the visible-light curing composition of forming shown in the preparation table 5 according to aforementioned evaluation method, with this solidification compound, solidifies the acquisition cured article by the rayed of using the radiation of visible light device, estimates surface not polymerization amount, hardness and polishing grindability.The result is shown in table 5 together.And, the absorption of water of the polymerizable monomer mixture that uses is shown in table 5.
<embodiment 21~22, Comparative Examples 18~19 〉
Prepare two kinds of composition A, B of composition as shown in table 5 respectively, they are mixed with solidification compound.With embodiment 19 in the same manner, this solidification compound is cured by rayed, the surface of estimating this cured article is polymerization amount, hardness and polishing grindability not.It the results are shown in table 5.And, in table 5, shown the absorption of water of the polymerizable monomer mixture that uses when preparing two kinds of compositions together.
[table 5]
Polymerisable monomer (monomer component A) | Water | Tensio-active agent | Polymerization starter | Filler | The surface is polymerization amount not | Hardness | The polishing grindability | |||||||
Type | Combined amount (mass parts) | Absorption of water | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | |||||
Embodiment 19 | Bis-GMA | 70 | 0.3 wt% | 3 | SLS | 1.5 | CQ | 0.07 | 3Si-Zr | 150 | 7μg /mm 2 | 24 | ○ | |
3G | 30 | DMBE | 0.08 | 0.3Si-Zr | 150 | |||||||||
Embodiment 20 | Bis-GMA | 56 | 2.5 wt% | 3 | SLS | 1.5 | CQ | 0.07 | 3Si-Zr | 150 | 1μg /mm 2 | 23 | ○ | |
3G | 24 | DMBE | 0.08 | 0.3Si-Zr | 150 | |||||||||
14G | 20 | |||||||||||||
Embodiment 21 | A | Bis-GMA | 20 | 0.3 wt% | 1.5 | SLS | 0.75 | DEPT | 0.5 | 3Si-Zr | 75 | 9μg /mm 2 | 20 | ○ |
3G | 30 | 0.3Si-Zr | 75 | |||||||||||
B | Bis-GMA | 20 | 1.5 | SLS | 0.75 | BPO | 1.5 | 3Si-Zr | 75 | |||||
3G | 30 | 0.3Si-Zr | 75 | |||||||||||
Embodiment 22 | A | Bis-GMA | 16 | 2.8 wt% | 1.5 | SLS | 0.75 | DEPT | 0.5 | 3Si-Zr | 75 | 3μg /mm 2 | 19 | ○ |
3G | 24 | 0.3Si-Zr | 75 | |||||||||||
14G | 10 | |||||||||||||
B | Bis-GMA | 16 | 1.5 | SLS | 0.75 | BPO | 1.5 | 3Si-Zr | 75 | |||||
3G | 24 | 0.3Si-Zr | 75 | |||||||||||
14G | 10 | |||||||||||||
Comparative Examples 16 | Bis-GMA | 70 | 0.3 wt% | - | SLS | - | CQ | 0.07 | 3Si-Zr | 150 | 568μg /mm 2 | 10 | × | |
3G | 30 | DMBE | 0.08 | 0.3Si-Zr | 150 | |||||||||
Comparative Examples 17 | Bi6-GMA | 56 | 2.5 wt% | - | SLS | - | CQ | 0.07 | 3Si-Zr | 150 | 553μg /mm 2 | 9 | × | |
3G | 24 | DMBE | 0.08 | 0.3Si-Zr | 150 | |||||||||
14G | 20 | |||||||||||||
Comparative Examples 18 | A | Bis-GMA | 20 | 0.3 wt% | - | SLS | - | DEPT | 0.5 | 3Si-Zr | 75 | 620μg /mm 2 | 8 | × |
3G | 30 | 0.3Si-Zr | 75 | |||||||||||
B | Bis-GMA | 20 | - | SLS | - | BPO | 1.5 | 3Si-Zr | 75 | |||||
3G | 30 | 0.3Si-Zr | 75 | |||||||||||
Comparative Examples 19 | A | Bis-GMA | 16 | 2.9 wt% | - | SLS | - | DEPT | 0.5 | 3Si-Zr | 75 | 610μg /mm 2 | 7 | × |
3G | 24 | 0.3Si-Zr | 75 | |||||||||||
14G | 10 | |||||||||||||
B | Bis-GMA | 16 | - | SLS | - | BPO | 1.5 | 3Si-Zr | 75 | |||||
3G | 24 | 0.3Si-Zr | 75 | |||||||||||
14G | 10 |
<implementation column 23, Comparative Examples 20 〉
Prepare two kinds of composition A, B of composition as shown in table 6 respectively, they are mixed with solidification compound.With embodiment 19 in the same manner, this solidification compound is cured by rayed, the surface of estimating this cured article is polymerization amount, hardness and polishing grindability not.It the results are shown in table 6.In addition, according to the blending ratio of the polymerisable monomer in the solidification compound of record in the table 6, the preparation polymerizable monomer mixture is measured absorption of water.This result is shown in table 6 together.
[table 6]
Polymerisable monomer (monomer component A) | Water | Tensio-active agent | Polymerization starter | Filler | The surface is polymerization amount not | Hardness | The polishing grindability | |||||||
Type | Combined amount (mass parts) | Absorption of water | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | |||||
Embodiment 23 | A | Bis-GMA | 15 | 2.9wt% | 1.5 | SLS | 0.75 | PhBTE0 A | 3 | 3Si-Zr | 75 | 12μg /mm 2 | 17 | ○ |
3G | 30 | |||||||||||||
HEMA | 5 | パ-ォクH | 0.75 | 0.3Si-Zr | 75 | |||||||||
B | PM | 15 | 1.5 | SLS | 0.75 | VOAA | 0.125 | 3Si-Zr | 75 | |||||
MAC-10 | 2.5 | |||||||||||||
D-2.6E | 22.5 | 0.3Si-Zr | 75 | |||||||||||
3G | 10 | |||||||||||||
Comparative Examples 20 | A | Bis-GMA | 15 | 2.9wt% | - | - | PhBTEO A | 3 | 3Si-Zr | 75 | 610μg /mm 2 | 6 | × | |
3G | 30 | |||||||||||||
HEMA | 5 | パ-ォクH | 0.75 | 0.3Si-Zr | 75 | |||||||||
B | PM | 15 | - | - | VOAA | 0.125 | 3Si-Zr | 75 | ||||||
MAC-10 | 2.5 | |||||||||||||
D-2.6E | 22.5 | 0.3Si-Zr | 75 | |||||||||||
3G | 10 |
<embodiment 24 〉
Use absorption of water as the 3G of 1.7wt% as polymerisable monomer, according to following formulation first liquid and second liquid.
The prescription of first liquid:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (anionic surfactant): 1.5 mass parts
POEL4 (nonionic surfactant) 1.5 mass parts
BPO (organo-peroxide): 3 mass parts
The prescription of second liquid:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (anionic surfactant): 1.5 mass parts
POEL4 (nonionic surfactant) 1.5 mass parts
DMPT (amine compound): 1.5 mass parts
First liquid and second liquid that will have aforesaid composition mix, and prepare the solidification compound of following composition.
The composition of solidification compound:
3G (monomer component (A)): 100 mass parts
Water: 3 mass parts
SLS (anionic surfactant): 1.5 mass parts
POEL4 (nonionic surfactant) 1.5 mass parts
BPO (organo-peroxide): 1.5 mass parts
DMPT (amine compound): 0.75 mass parts
To this solidification compound, estimate surface not polymerization amount, flexural strength and package stability (whether having tensio-active agent to separate out).Consequently the surface not polymerization amount be 3 μ g/mm
2, the flexural strength of cured article is 80MPa.And, in storage stability test, do not see that tensio-active agent separates out.The composition of solidification compound, surface not polymerization amount and package stability the results are shown in table 7.
<embodiment 25~31 〉
Except the type of the tensio-active agent that uses such as table 7 record change, prepare solidification compound in the same manner with embodiment 24, the gained solidification compound is carried out the not evaluation of polymerization amount and package stability of surface.The results are shown in table 7.In addition, the result who in table 7, has shown embodiment 1 together.
[table 7]
Polymerisable monomer * | Water | The anionic surfactant | Nonionic surfactant | Polymerization starter | The surface is polymerization amount not | Tensio-active agent is separated out | ||||
Type | Combined amount (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | |||
Embodiment 24 | 3G | 100 | 3 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 3μg/mm 2 | ○ |
Embodiment 25 | 3G | 100 | 3 | SLS | 1.5 | POEL10 | 1.5 | 1.5/0.75 | 4μg/mm 2 | ○ |
Embodiment 26 | 3G | 100 | 3 | SLS | 1.5 | POEO2 | 1.5 | 1.5/0.75 | 4μg/mm 2 | ○ |
Embodiment 27 | 3G | 100 | 3 | SLS | 1.5 | POEO7 | 1.5 | 1.5/0.75 | 4μg/mm 2 | ○ |
Embodiment 28 | 3G | 100 | 3 | SLS | 1.5 | POEO15 | 1.5 | 1.5/0.75 | 4μg/mm 2 | ○ |
Embodiment 29 | 3G | 100 | 3 | SDS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 3μg/mm 2 | ○ |
Embodiment 30 | 3G | 100 | 3 | SOS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 3μg/mm 2 | ○ |
Embodiment 31 | 3G | 100 | 3 | LBS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 7μg/mm 2 | ○ |
Embodiment 1 | 3G | 100 | 3 | SLS | - | - | - | 1.5/0.75 | 5μg/mm 2 | - |
*: the absorption of water of 3G is 1.7wt%
<embodiment 32 〉
Except using HD the monomer as free redical polymerization of absorption of water, prepare solidification compound in the same manner with embodiment 24 as 0.1wt%.The solidification compound that obtains is carried out the evaluation of surperficial not polymerization amount and package stability, the results are shown in table 8.In addition, the result who in table 8, has shown embodiment 6 together.
And surface not polymerization amount is 5 μ g/mm
2, do not see that in storage stability test tensio-active agent separates out.
<embodiment 33 〉
The mixture for preparing 70 mass parts AAEM and 30 mass parts HEMA is as polymerisable monomer.The absorption of water of measuring this polymerizable monomer mixture is 10.3wt%.
Except using said mixture to replace preparing solidification compound in the same manner with embodiment 24 3G.Carry out the mensuration of surperficial not polymerization amount and package stability, the results are shown in table 8.
And surface not polymerization amount is 8 μ g/mm
2, do not see that in storage stability test tensio-active agent separates out.
<embodiment 34~36 〉
Use the AAEM of composition as shown in table 8 and the polymerizable monomer mixture of HEMA, prepare solidification compound in the same manner, carry out the mensuration of surperficial not polymerization amount and package stability, the results are shown in table 8 with embodiment 24.
And, in table 8, shown the absorption of water of polymerizable monomer mixture together.
[table 8]
Polymerisable monomer (monomer component A) | Water | The anionic surfactant | Nonionic surfactant | Polymerization starter | The surface is polymerization amount not | Tensio-active agent is separated out | |||||
Type | Combined amount absorption of water (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | ||||
Embodiment 32 | HD | 100 | 0.1wt% | 3 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 5μg/mm 2 | ○ |
Embodiment 33 | AAEM | 70 | 10.3wt% | 3 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 8μg/mm 2 | ○ |
HEMA | 30 | ||||||||||
Embodiment 34 | AAEM | 50 | 16.4wt% | 3 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 38μg/mm 2 | ○ |
HEMA | 50 | ||||||||||
Embodiment 35 | AAEM | 50 | 16.4wt% | 5 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 6μg/mm 2 | ○ |
HEMA | 50 | ||||||||||
Embodiment 36 | AAEM | 30 | 23.3wt% | 5 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 43μg/mm 2 | ○ |
HEMA | 70 | ||||||||||
Embodiment 6 | HD | 100 | 0.1wt% | 3 | SLS | 3 | - | - | 1.5/0.75 | 7μg/mm 2 | × |
<embodiment 37,38 〉
Except the combined amount that changes water, prepare the solidification compound of forming shown in the table 9 in the same manner with embodiment 24, carry out the not evaluation of polymerization amount, flexural strength and package stability of surface.Its result is shown in table 9 with the result of embodiment 24.
[table 9]
Polymerisable monomer * | Water | The anionic surfactant | Nonionic surfactant | Polymerization starter | The surface is polymerization amount not | Flexural strength | Tensio-active agent is separated out | ||||
Type | Combined amount (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | ||||
Embodiment 24 | 3G | 100 | 3 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 3μg/mm 2 | 80MPa | ○ |
Embodiment 37 | 3G | 100 | 1 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 29μg/mm 2 | 82MPa | ○ |
Embodiment 38 | 3G | 100 | 5 | SLS | 1.5 | POEL4 | 1.5 | 1.5/0.75 | 2μg/mm 2 | 76MPa | ○ |
*: the absorption of water of 3G is 1.7wt%
<embodiment 39 〉
According to the composition shown in the table 10, polymerisable monomer, water, tensio-active agent, water-soluble polymers and polymerization starter are mixed the preparation solidification compound.This solidification compound is carried out the not mensuration of polymerization amount of surface, the results are shown in table 10.
<Comparative Examples 21 〉
Except not using fully the tensio-active agent, prepare solidification compound in the same manner with embodiment 39, carry out the not mensuration of polymerization amount of surface, the results are shown in table 10.
<embodiment 40~43 〉
Except the type that changes tensio-active agent, prepare solidification compound in the same manner with embodiment 39, carry out the not mensuration of polymerization amount of surface, the results are shown in table 10.
As shown in Table 10, by with water-soluble polymers and tensio-active agent and usefulness, can make the surface not polymerization amount reduce greatly.
[table 10]
Polymerisable monomer | Water | Water-soluble polymers | Tensio-active agent | Polymerization starter | The surface is polymerization amount not | ||||
Type | Combined amount (mass parts) | Combined amount (mass parts) | Type | Combined amount (mass parts) | Type | Combined amount (mass parts) | BPO/DMPT (mass parts) | ||
Comparative Examples 21 | 3G | 100 | 3 | PVA1000 | 0.01 | - | - | 1.5/0.75 | 83μg/mm 2 |
Embodiment 39 | 3G | 100 | 3 | PVA1000 | 0.01 | SLS | 1.5 | 1.5/0.75 | 3μg/mm 2 |
Embodiment 40 | 3G | 100 | 3 | PVA1000 | 0.01 | SDS | 1.5 | 1.5/0.75 | 2μg/mm 2 |
Embodiment 41 | 3G | 100 | 3 | PVA1000 | 0.01 | LDAGCI | 1.5 | 1.5/0.75 | 7μg/mm 2 |
Embodiment 42 | 3G | 100 | 3 | PVA1000 | 0.01 | LTMACI | 1.5 | 1.5/0.75 | 18μg/mm 2 |
Embodiment 43 | 3G | 100 | 3 | PVA1000 | 0.01 | POEL | 1.5 | 1.5/0.75 | 21μg/mm 2 |
Claims (7)
1, a kind of solidification compound comprises:
(A) form by the monomer of free redical polymerization and absorption of water is 20wt% or lower monomer component 100 mass parts;
(B) water 0.5~10 mass parts;
(C) tensio-active agent 0.1~20 mass parts; With
(D) radical polymerization initiator of significant quantity.
2, the solidification compound of claim 1, aforementioned monomer composition (A) are that absorption of water is that 5wt% or lower strong-hydrophobicity polymerisable monomer (a-1) and absorption of water are the mixture of 100wt% or higher strongly hydrophilic polymerisable monomer (a-2).
3, the solidification compound of claim 1, aforementioned surfactants (C) is made up of anionic surfactant (c-1) and nonionic surfactant (c-2).
4, the solidification compound of claim 3, the aforementioned monomer composition (A) of relative 100 mass parts contains the aforementioned anionic surfactant (c-1) of 0.1~10 mass parts and the aforementioned nonionic surfactant (c-2) of 0.1~10 mass parts.
5, the solidification compound of claim 1, the aforementioned monomer composition (A) of relative 100 mass parts also contains the water-soluble polymers (E) of 0.00001~10 mass parts.
6, the solidification compound of claim 1 is cured by radical polymerization under the state that keeps aforementioned water (B).
7, the application of the solidification compound of claim 1 in the dental repair materials.
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CN106659639A (en) * | 2014-07-11 | 2017-05-10 | 三井化学株式会社 | Dental prosthesis |
CN111050694A (en) * | 2017-09-11 | 2020-04-21 | 3M创新有限公司 | Radiation curable compositions and composite articles made using additive manufacturing processes |
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US7081485B2 (en) * | 2002-08-21 | 2006-07-25 | Bisco, Inc. | Non-volatile dental compositions containing multifunctional acrylate compounds and lacking an oxygen-inhibited layer |
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CN111050694A (en) * | 2017-09-11 | 2020-04-21 | 3M创新有限公司 | Radiation curable compositions and composite articles made using additive manufacturing processes |
US11553996B2 (en) | 2017-09-11 | 2023-01-17 | 3M Innovative Properties Company | Radiation curable compositions and composite articles made using an additive manufacturing process |
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