JPH0461003B2 - - Google Patents

Info

Publication number: JPH0461003B2
Authority: JP; Japan
Prior art keywords: paste; inorganic oxide; weight; vinyl monomer; composite
Prior art date: 1983-06-30
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.): Expired - Lifetime

Application number

JP58116839A

Other languages

English (en)

Japanese (ja)

Other versions

JPS6011505A (ja

Inventor

Shigeki Yuasa

Koji Kusumoto

Namihiro Okabayashi

Katsumi Suzuki

Hideki Oono

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Tokuyama Corp

Original Assignee

Tokuyama Corp

Priority date (The priority date 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 date listed.)

1983-06-30

Filing date

1983-06-30

Publication date

1992-09-29

1983-06-30 Application filed by Tokuyama Corp filed Critical Tokuyama Corp

1983-06-30 Priority to JP58116839A priority Critical patent/JPS6011505A/ja

1985-01-21 Publication of JPS6011505A publication Critical patent/JPS6011505A/ja

1992-09-29 Publication of JPH0461003B2 publication Critical patent/JPH0461003B2/ja

Status Granted legal-status Critical Current

Links

239000000203 mixture Substances 0.000 claims description 110
239000002131 composite material Substances 0.000 claims description 100
229920002554 vinyl polymer Polymers 0.000 claims description 98
239000000178 monomer Substances 0.000 claims description 97
229910052809 inorganic oxide Inorganic materials 0.000 claims description 95
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 91
239000002245 particle Substances 0.000 claims description 59
239000000945 filler Substances 0.000 claims description 53
238000006116 polymerization reaction Methods 0.000 claims description 44
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 claims description 36
239000000377 silicon dioxide Substances 0.000 claims description 17
150000001451 organic peroxides Chemical class 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
230000000737 periodic effect Effects 0.000 claims description 11
229910044991 metal oxide Inorganic materials 0.000 claims description 7
150000004706 metal oxides Chemical class 0.000 claims description 7
239000000470 constituent Substances 0.000 claims description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 57
229920000642 polymer Polymers 0.000 description 42
238000002156 mixing Methods 0.000 description 28
239000011259 mixed solution Substances 0.000 description 22
239000000243 solution Substances 0.000 description 21
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 20
238000000034 method Methods 0.000 description 18
230000000704 physical effect Effects 0.000 description 18
BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 16
ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 14
238000004519 manufacturing process Methods 0.000 description 14
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 13
238000009826 distribution Methods 0.000 description 13
239000002904 solvent Substances 0.000 description 13
239000000463 material Substances 0.000 description 12
230000000379 polymerizing effect Effects 0.000 description 11
239000000843 powder Substances 0.000 description 10
238000003756 stirring Methods 0.000 description 10
238000006243 chemical reaction Methods 0.000 description 9
239000011521 glass Substances 0.000 description 9
238000004898 kneading Methods 0.000 description 9
238000012360 testing method Methods 0.000 description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
239000007795 chemical reaction product Substances 0.000 description 8
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 7
239000003505 polymerization initiator Substances 0.000 description 7
239000001294 propane Substances 0.000 description 7
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
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 6
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 6
150000007824 aliphatic compounds Chemical class 0.000 description 6
238000005452 bending Methods 0.000 description 6
YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 6
230000003746 surface roughness Effects 0.000 description 6
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 5
239000004342 Benzoyl peroxide Substances 0.000 description 5
235000019400 benzoyl peroxide Nutrition 0.000 description 5
239000012295 chemical reaction liquid Substances 0.000 description 5
238000010304 firing Methods 0.000 description 5
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
-1 Aliphatic compounds Ethylene glycol dimethacrylate Chemical class 0.000 description 4
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 4
XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-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
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
239000011350 dental composite resin Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
230000005484 gravity Effects 0.000 description 4
229910052751 metal Inorganic materials 0.000 description 4
239000002184 metal Substances 0.000 description 4
229910052757 nitrogen Inorganic materials 0.000 description 4
150000003961 organosilicon compounds Chemical class 0.000 description 4
JUVSRZCUMWZBFK-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-4-methylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1 JUVSRZCUMWZBFK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 3
VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 3
238000005299 abrasion Methods 0.000 description 3
150000001252 acrylic acid derivatives Chemical class 0.000 description 3
239000007864 aqueous solution Substances 0.000 description 3
150000001491 aromatic compounds Chemical class 0.000 description 3
VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000007788 liquid Substances 0.000 description 3
238000011068 loading method Methods 0.000 description 3
238000005259 measurement Methods 0.000 description 3
239000012299 nitrogen atmosphere Substances 0.000 description 3
239000000047 product Substances 0.000 description 3
239000002994 raw material Substances 0.000 description 3
238000004381 surface treatment Methods 0.000 description 3
WRXCBRHBHGNNQA-UHFFFAOYSA-N (2,4-dichlorobenzoyl) 2,4-dichlorobenzenecarboperoxoate Chemical compound ClC1=CC(Cl)=CC=C1C(=O)OOC(=O)C1=CC=C(Cl)C=C1Cl WRXCBRHBHGNNQA-UHFFFAOYSA-N 0.000 description 2
UWNADWZGEHDQAB-UHFFFAOYSA-N 2,5-dimethylhexane Chemical compound CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-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
238000004438 BET method Methods 0.000 description 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 2
OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 2
MCMNRKCIXSYSNV-UHFFFAOYSA-N Zirconium dioxide Chemical compound O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 2
ULQMPOIOSDXIGC-UHFFFAOYSA-N [2,2-dimethyl-3-(2-methylprop-2-enoyloxy)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(C)COC(=O)C(C)=C ULQMPOIOSDXIGC-UHFFFAOYSA-N 0.000 description 2
JUDXBRVLWDGRBC-UHFFFAOYSA-N [2-(hydroxymethyl)-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(CO)(COC(=O)C(C)=C)COC(=O)C(C)=C JUDXBRVLWDGRBC-UHFFFAOYSA-N 0.000 description 2
SJSXBTSSSQCODU-UHFFFAOYSA-N [4-[2-[2,3-diethoxy-4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]-2,3-diethoxyphenyl] 2-methylprop-2-enoate Chemical compound CCOC1=C(OC(=O)C(C)=C)C=CC(C(C)(C)C=2C(=C(OCC)C(OC(=O)C(C)=C)=CC=2)OCC)=C1OCC SJSXBTSSSQCODU-UHFFFAOYSA-N 0.000 description 2
229910052786 argon Inorganic materials 0.000 description 2
QVQLCTNNEUAWMS-UHFFFAOYSA-N barium oxide Chemical compound [Ba]=O QVQLCTNNEUAWMS-UHFFFAOYSA-N 0.000 description 2
ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 2
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
150000001875 compounds Chemical class 0.000 description 2
ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
238000001035 drying Methods 0.000 description 2
238000011049 filling Methods 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 2
239000004570 mortar (masonry) Substances 0.000 description 2
GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 2
150000002894 organic compounds Chemical class 0.000 description 2
NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
RZXMPPFPUUCRFN-UHFFFAOYSA-N p-toluidine Chemical compound CC1=CC=C(N)C=C1 RZXMPPFPUUCRFN-UHFFFAOYSA-N 0.000 description 2
239000003504 photosensitizing agent Substances 0.000 description 2
238000005498 polishing Methods 0.000 description 2
238000010298 pulverizing process Methods 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
238000001878 scanning electron micrograph Methods 0.000 description 2
DVQHRBFGRZHMSR-UHFFFAOYSA-N sodium methyl 2,2-dimethyl-4,6-dioxo-5-(N-prop-2-enoxy-C-propylcarbonimidoyl)cyclohexane-1-carboxylate Chemical compound [Na+].C=CCON=C(CCC)[C-]1C(=O)CC(C)(C)C(C(=O)OC)C1=O DVQHRBFGRZHMSR-UHFFFAOYSA-N 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003860 storage Methods 0.000 description 2
IATRAKWUXMZMIY-UHFFFAOYSA-N strontium oxide Chemical compound [O-2].[Sr+2] IATRAKWUXMZMIY-UHFFFAOYSA-N 0.000 description 2
239000000126 substance Substances 0.000 description 2
KIZCNUWGIVQQBK-UHFFFAOYSA-N (2-hydroxy-4-methylphenyl)-phenylmethanone Chemical compound OC1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 KIZCNUWGIVQQBK-UHFFFAOYSA-N 0.000 description 1
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 1
SWFHGTMLYIBPPA-UHFFFAOYSA-N (4-methoxyphenyl)-phenylmethanone Chemical compound C1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 SWFHGTMLYIBPPA-UHFFFAOYSA-N 0.000 description 1
229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 1
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 description 1
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 1
QWQNFXDYOCUEER-UHFFFAOYSA-N 2,3-ditert-butyl-4-methylphenol Chemical compound CC1=CC=C(O)C(C(C)(C)C)=C1C(C)(C)C QWQNFXDYOCUEER-UHFFFAOYSA-N 0.000 description 1
JJBFVQSGPLGDNX-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)propyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)COC(=O)C(C)=C JJBFVQSGPLGDNX-UHFFFAOYSA-N 0.000 description 1
HXCWOOAEAHVMBJ-UHFFFAOYSA-N 2-(n,4-dimethylanilino)ethanol Chemical compound OCCN(C)C1=CC=C(C)C=C1 HXCWOOAEAHVMBJ-UHFFFAOYSA-N 0.000 description 1
FEXBEKLLSUWSIM-UHFFFAOYSA-N 2-Butyl-4-methylphenol Chemical group CCCCC1=CC(C)=CC=C1O FEXBEKLLSUWSIM-UHFFFAOYSA-N 0.000 description 1
LBLYYCQCTBFVLH-UHFFFAOYSA-N 2-Methylbenzenesulfonic acid Chemical class CC1=CC=CC=C1S(O)(=O)=O LBLYYCQCTBFVLH-UHFFFAOYSA-N 0.000 description 1
VIYWVRIBDZTTMH-UHFFFAOYSA-N 2-[4-[2-[4-[2-(2-methylprop-2-enoyloxy)ethoxy]phenyl]propan-2-yl]phenoxy]ethyl 2-methylprop-2-enoate Chemical compound C1=CC(OCCOC(=O)C(=C)C)=CC=C1C(C)(C)C1=CC=C(OCCOC(=O)C(C)=C)C=C1 VIYWVRIBDZTTMH-UHFFFAOYSA-N 0.000 description 1
DMTMWMUHQLDCKP-UHFFFAOYSA-N 2-[n-(2-hydroxyethyl)-3,4-dimethylanilino]ethanol Chemical compound CC1=CC=C(N(CCO)CCO)C=C1C DMTMWMUHQLDCKP-UHFFFAOYSA-N 0.000 description 1
KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 1
UGVRJVHOJNYEHR-UHFFFAOYSA-N 4-chlorobenzophenone Chemical compound C1=CC(Cl)=CC=C1C(=O)C1=CC=CC=C1 UGVRJVHOJNYEHR-UHFFFAOYSA-N 0.000 description 1
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 1
238000007546 Brinell hardness test Methods 0.000 description 1
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 1
244000028419 Styrax benzoin Species 0.000 description 1
235000000126 Styrax benzoin Nutrition 0.000 description 1
235000008411 Sumatra benzointree Nutrition 0.000 description 1
238000003917 TEM image Methods 0.000 description 1
LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
238000002441 X-ray diffraction Methods 0.000 description 1
VSXPEHGZLDNBNU-UHFFFAOYSA-N [2,3,5,6-tetraethoxy-4-[2-[2,3,5,6-tetraethoxy-4-(2-methylprop-2-enoyloxy)phenyl]propan-2-yl]phenyl] 2-methylprop-2-enoate Chemical compound CCOC1=C(OC(=O)C(C)=C)C(OCC)=C(OCC)C(C(C)(C)C=2C(=C(OCC)C(OC(=O)C(C)=C)=C(OCC)C=2OCC)OCC)=C1OCC VSXPEHGZLDNBNU-UHFFFAOYSA-N 0.000 description 1
SWHLOXLFJPTYTL-UHFFFAOYSA-N [2-methyl-3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(C)(COC(=O)C(C)=C)COC(=O)C(C)=C SWHLOXLFJPTYTL-UHFFFAOYSA-N 0.000 description 1
FOVRCPBDDCLNIG-UHFFFAOYSA-N [3-(2-methylprop-2-enoyloxy)-2-(2-methylprop-2-enoyloxymethyl)propyl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCC(COC(=O)C(C)=C)COC(=O)C(C)=C FOVRCPBDDCLNIG-UHFFFAOYSA-N 0.000 description 1
UUQJMSSFMULZHR-UHFFFAOYSA-N [4,5,5,6,6-pentaethoxy-4-[2-[1,5,5,6,6-pentaethoxy-4-(2-methylprop-2-enoyloxy)cyclohex-2-en-1-yl]propan-2-yl]cyclohex-2-en-1-yl] 2-methylprop-2-enoate Chemical compound C(C(=C)C)(=O)OC1C(C(C(C=C1)(C(C)(C)C1(C(C(C(C=C1)OC(C(=C)C)=O)(OCC)OCC)(OCC)OCC)OCC)OCC)(OCC)OCC)(OCC)OCC UUQJMSSFMULZHR-UHFFFAOYSA-N 0.000 description 1
RRXMSCIBDRKLQO-UHFFFAOYSA-N [4-[2-[4-(2-methylprop-2-enoyloxy)-2,3-dipropoxyphenyl]propan-2-yl]-2,3-dipropoxyphenyl] 2-methylprop-2-enoate Chemical compound CCCOC1=C(OC(=O)C(C)=C)C=CC(C(C)(C)C=2C(=C(OCCC)C(OC(=O)C(C)=C)=CC=2)OCCC)=C1OCCC RRXMSCIBDRKLQO-UHFFFAOYSA-N 0.000 description 1
238000010521 absorption reaction Methods 0.000 description 1
239000002253 acid Substances 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
230000002411 adverse Effects 0.000 description 1
239000012670 alkaline solution Substances 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
229910052788 barium Inorganic materials 0.000 description 1
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 1
239000011324 bead Substances 0.000 description 1
229960002130 benzoin Drugs 0.000 description 1
BSDOQSMQCZQLDV-UHFFFAOYSA-N butan-1-olate;zirconium(4+) Chemical compound [Zr+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] BSDOQSMQCZQLDV-UHFFFAOYSA-N 0.000 description 1
238000004364 calculation method Methods 0.000 description 1
239000000805 composite resin Substances 0.000 description 1
230000007547 defect Effects 0.000 description 1
230000004069 differentiation Effects 0.000 description 1
ROOKZAOKJQNELK-UHFFFAOYSA-N diphenylmethanone;3-hydroxybutan-2-one Chemical compound CC(O)C(C)=O.C=1C=CC=CC=1C(=O)C1=CC=CC=C1 ROOKZAOKJQNELK-UHFFFAOYSA-N 0.000 description 1
238000002845 discoloration Methods 0.000 description 1
BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
IDGUHHHQCWSQLU-UHFFFAOYSA-N ethanol;hydrate Chemical compound O.CCO IDGUHHHQCWSQLU-UHFFFAOYSA-N 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
SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 1
STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
238000011156 evaluation Methods 0.000 description 1
239000010419 fine particle Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
235000019382 gum benzoic Nutrition 0.000 description 1
230000007062 hydrolysis Effects 0.000 description 1
238000006460 hydrolysis reaction Methods 0.000 description 1
239000011261 inert gas Substances 0.000 description 1
239000011256 inorganic filler Substances 0.000 description 1
229910003475 inorganic filler Inorganic materials 0.000 description 1
230000001788 irregular Effects 0.000 description 1
MKARNSWMMBGSHX-UHFFFAOYSA-N m-xylylamine Natural products CC1=CC(C)=CC(N)=C1 MKARNSWMMBGSHX-UHFFFAOYSA-N 0.000 description 1
125000005395 methacrylic acid group Chemical group 0.000 description 1
239000012046 mixed solvent Substances 0.000 description 1
210000000214 mouth Anatomy 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002902 organometallic compounds Chemical class 0.000 description 1
QRMPKOFEUHIBNM-UHFFFAOYSA-N p-dimethylcyclohexane Natural products CC1CCC(C)CC1 QRMPKOFEUHIBNM-UHFFFAOYSA-N 0.000 description 1
150000002989 phenols Chemical class 0.000 description 1
239000000049 pigment Substances 0.000 description 1
229960005235 piperonyl butoxide Drugs 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
229920000058 polyacrylate Polymers 0.000 description 1
230000001376 precipitating effect Effects 0.000 description 1
238000002360 preparation method 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
239000010453 quartz Substances 0.000 description 1
238000010992 reflux Methods 0.000 description 1
238000004626 scanning electron microscopy Methods 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
125000005372 silanol group Chemical group 0.000 description 1
150000003377 silicon compounds Chemical class 0.000 description 1
KKCBUQHMOMHUOY-UHFFFAOYSA-N sodium oxide Chemical compound [O-2].[Na+].[Na+] KKCBUQHMOMHUOY-UHFFFAOYSA-N 0.000 description 1
229910001948 sodium oxide Inorganic materials 0.000 description 1
239000012798 spherical particle Substances 0.000 description 1
BSMBUEVFPXLCNC-UHFFFAOYSA-N strontium;methanolate Chemical compound CO[Sr]OC BSMBUEVFPXLCNC-UHFFFAOYSA-N 0.000 description 1
238000004441 surface measurement Methods 0.000 description 1
GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
238000010998 test method Methods 0.000 description 1
239000011882 ultra-fine particle Substances 0.000 description 1
239000006097 ultraviolet radiation absorber Substances 0.000 description 1

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Dental Preparations (AREA)
Polymerisation Methods In General (AREA)

JP58116839A 1983-06-30 1983-06-30 重合用の複合組成物 Granted JPS6011505A (ja)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP58116839A JPS6011505A (ja)	1983-06-30	1983-06-30	重合用の複合組成物

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP58116839A JPS6011505A (ja)	1983-06-30	1983-06-30	重合用の複合組成物

Publications (2)

Publication Number	Publication Date
JPS6011505A JPS6011505A (ja)	1985-01-21
JPH0461003B2 true JPH0461003B2 (de)	1992-09-29

Family

ID=14696899

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP58116839A Granted JPS6011505A (ja)	1983-06-30	1983-06-30	重合用の複合組成物

Country Status (1)

Country	Link
JP (1)	JPS6011505A (de)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5762405B2 (ja) *	2010-06-18	2015-08-12	株式会社トクヤマデンタル	歯科用複合修復材料

Families Citing this family (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5022553B2 (ja)	2000-08-11	2012-09-12	サンメディカル株式会社	重合性組成物、その硬化物および複合材料
JP5082179B2 (ja) *	2001-09-14	2012-11-28	昭和電工株式会社	シリカ被覆混晶酸化物粒子、その製法及びそれを用いた化粧料
KR102017065B1 (ko)	2015-10-21	2019-09-02	가부시키가이샤 도쿠야마 덴탈	경화성 조성물 및 치과용 충전 수복 재료
US11273104B2 (en)	2017-03-06	2022-03-15	Tokuyama Dental Corporation	Photocurable composition and dental restoration filling material
JP7422994B2 (ja) *	2019-11-26	2024-01-29	株式会社トクヤマデンタル	歯科用硬化性組成物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS497336A (de) *	1972-03-21	1974-01-23
JPS53115768A (en) *	1977-03-22	1978-10-09	Mitsubishi Rayon Co Ltd	Preparation of marblelike cured material
JPS5415991A (en) *	1977-04-22	1979-02-06	Hofacker Frauke	Polymerizable composition for making dental plastics
JPS5944304A (ja) *	1982-08-02	1984-03-12	ジヨンソン・アンド・ジヨンソン・デンタル・プロダクツ・カンパニ−	歯科用補強組成物

1983
- 1983-06-30 JP JP58116839A patent/JPS6011505A/ja active Granted

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JPS497336A (de) *	1972-03-21	1974-01-23
JPS53115768A (en) *	1977-03-22	1978-10-09	Mitsubishi Rayon Co Ltd	Preparation of marblelike cured material
JPS5415991A (en) *	1977-04-22	1979-02-06	Hofacker Frauke	Polymerizable composition for making dental plastics
JPS5944304A (ja) *	1982-08-02	1984-03-12	ジヨンソン・アンド・ジヨンソン・デンタル・プロダクツ・カンパニ−	歯科用補強組成物

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
JP5762405B2 (ja) *	2010-06-18	2015-08-12	株式会社トクヤマデンタル	歯科用複合修復材料

Also Published As

Publication number	Publication date
JPS6011505A (ja)	1985-01-21

Publication	Publication Date	Title
US5609675A (en)	1997-03-11	Inorganic composition
Ergun et al.	2018	The effects of adding various ratios of zirconium oxide nanoparticles to poly (methyl methacrylate) on physical and mechanical properties
US6849670B2 (en)	2005-02-01	Photo-curable reparative material for dental use
US7670580B2 (en)	2010-03-02	Dental resin materials, method of manufacture, and uses thereof
JP2732968B2 (ja)	1998-03-30	歯科用充填組成物
JP3487395B2 (ja)	2004-01-19	硬化性組成物
US7820733B2 (en)	2010-10-26	Dental polymerizable core build-up material of separately packed type
WO2002015847A1 (fr)	2002-02-28	Composition dentaire durcissable
JP2005517688A (ja)	2005-06-16	歯科ペースト、歯科物品、および方法
JPH0425246B2 (de)	1992-04-30
US9296891B2 (en)	2016-03-29	Dental resin materials, method of manufacture, and uses thereof
JPH0461003B2 (de)	1992-09-29
JPH0312044B2 (de)	1991-02-19
JP4798680B2 (ja)	2011-10-19	歯科用硬化性組成物
JPH0312043B2 (de)	1991-02-19
JPS61171404A (ja)	1986-08-02	複合修復材
JP2523993B2 (ja)	1996-08-14	歯科用複合材料の製造方法
JPH0157082B2 (de)	1989-12-04
JPH0310603B2 (de)	1991-02-14
RU2821202C1 (ru)	2024-06-18	Отверждаемая композиция для стоматологии
JPH0755883B2 (ja)	1995-06-14	複合修復材
WO2023042598A1 (ja)	2023-03-23	Ｘ線不透過性充填材、歯科用ｘ線不透過性充填材、ｘ線不透過性充填材の製造方法、及び、歯科用硬化性組成物
JPS6011408A (ja)	1985-01-21	複合充填材
JP7289485B2 (ja)	2023-06-12	歯科用硬化性組成物
JPH0322842B2 (de)	1991-03-27

JPH0461003B2 - - Google Patents

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Priority Applications (1)

Applications Claiming Priority (1)

Publications (2)

Family

ID=14696899

Family Applications (1)

Country Status (1)

Cited By (1)

Families Citing this family (5)

Citations (4)

Patent Citations (4)

Cited By (1)

Also Published As

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