JPH034041B2 - - Google Patents
Info
- Publication number
- JPH034041B2 JPH034041B2 JP58115711A JP11571183A JPH034041B2 JP H034041 B2 JPH034041 B2 JP H034041B2 JP 58115711 A JP58115711 A JP 58115711A JP 11571183 A JP11571183 A JP 11571183A JP H034041 B2 JPH034041 B2 JP H034041B2
- Authority
- JP
- Japan
- Prior art keywords
- dicyclopentenyl
- dental material
- group
- acrylic resin
- parts
- 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.)
- Expired
Links
- 239000004925 Acrylic resin Substances 0.000 claims description 24
- 229920000178 Acrylic resin Polymers 0.000 claims description 24
- 239000000178 monomer Substances 0.000 claims description 23
- 239000005548 dental material Substances 0.000 claims description 22
- -1 acrylic ester Chemical class 0.000 claims description 15
- 239000000945 filler Substances 0.000 claims description 10
- 239000003505 polymerization initiator Substances 0.000 claims description 9
- 239000000843 powder Substances 0.000 claims description 7
- 230000009477 glass transition Effects 0.000 claims description 6
- LUCXVPAZUDVVBT-UHFFFAOYSA-N methyl-[3-(2-methylphenoxy)-3-phenylpropyl]azanium;chloride Chemical compound Cl.C=1C=CC=CC=1C(CCNC)OC1=CC=CC=C1C LUCXVPAZUDVVBT-UHFFFAOYSA-N 0.000 claims description 6
- 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 claims description 5
- AQNSVANSEBPSMK-UHFFFAOYSA-N dicyclopentenyl methacrylate Chemical compound C12CC=CC2C2CC(OC(=O)C(=C)C)C1C2.C12C=CCC2C2CC(OC(=O)C(=C)C)C1C2 AQNSVANSEBPSMK-UHFFFAOYSA-N 0.000 claims description 5
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 239000002131 composite material Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 description 18
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 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 6
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- 239000010453 quartz Substances 0.000 description 4
- 239000011342 resin composition Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000004342 Benzoyl peroxide Substances 0.000 description 3
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
- 235000019400 benzoyl peroxide Nutrition 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 239000004926 polymethyl methacrylate Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 description 2
- 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 2
- INQDDHNZXOAFFD-UHFFFAOYSA-N 2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOC(=O)C=C INQDDHNZXOAFFD-UHFFFAOYSA-N 0.000 description 2
- 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 2
- HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 description 2
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 2
- 229910002012 Aerosil® Inorganic materials 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-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
- 238000010521 absorption reaction Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004132 cross linking Methods 0.000 description 2
- 208000002925 dental caries Diseases 0.000 description 2
- 239000003479 dental cement Substances 0.000 description 2
- ZQMIGQNCOMNODD-UHFFFAOYSA-N diacetyl peroxide Chemical compound CC(=O)OOC(C)=O ZQMIGQNCOMNODD-UHFFFAOYSA-N 0.000 description 2
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 2
- 239000003955 fissure sealant Substances 0.000 description 2
- 125000005395 methacrylic acid group Chemical group 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 229910000077 silane Inorganic materials 0.000 description 2
- 238000004381 surface treatment Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 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
- JMIZWXDKTUGEES-UHFFFAOYSA-N 2,2-di(cyclopenten-1-yloxy)ethyl 2-methylprop-2-enoate Chemical compound C=1CCCC=1OC(COC(=O)C(=C)C)OC1=CCCC1 JMIZWXDKTUGEES-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- 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 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- CFVWNXQPGQOHRJ-UHFFFAOYSA-N 2-methylpropyl prop-2-enoate Chemical compound CC(C)COC(=O)C=C CFVWNXQPGQOHRJ-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
- FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 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 1
- JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-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
- FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- 239000006087 Silane Coupling Agent Substances 0.000 description 1
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 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
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-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
- 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 1
- 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 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 125000000751 azo group Chemical group [*]N=N[*] 0.000 description 1
- 239000007869 azo polymerization initiator 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
- 238000005452 bending Methods 0.000 description 1
- 229960002130 benzoin Drugs 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 239000005388 borosilicate glass Substances 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- UPIWXMRIPODGLE-UHFFFAOYSA-N butyl benzenecarboperoxoate Chemical compound CCCCOOC(=O)C1=CC=CC=C1 UPIWXMRIPODGLE-UHFFFAOYSA-N 0.000 description 1
- 239000011797 cavity material Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 239000011350 dental composite resin Substances 0.000 description 1
- 210000003298 dental enamel Anatomy 0.000 description 1
- ISAOCJYIOMOJEB-UHFFFAOYSA-N desyl alcohol Natural products C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 description 1
- HNPSIPDUKPIQMN-UHFFFAOYSA-N dioxosilane;oxo(oxoalumanyloxy)alumane Chemical compound O=[Si]=O.O=[Al]O[Al]=O HNPSIPDUKPIQMN-UHFFFAOYSA-N 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 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
- 238000011156 evaluation Methods 0.000 description 1
- 238000009408 flooring Methods 0.000 description 1
- 239000002241 glass-ceramic Substances 0.000 description 1
- 235000019382 gum benzoic Nutrition 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- CDOSHBSSFJOMGT-UHFFFAOYSA-N linalool Chemical compound CC(C)=CCCC(C)(O)C=C CDOSHBSSFJOMGT-UHFFFAOYSA-N 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 description 1
- 210000000214 mouth Anatomy 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- RSVDRWTUCMTKBV-UHFFFAOYSA-N sbb057044 Chemical compound C12CC=CC2C2CC(OCCOC(=O)C=C)C1C2 RSVDRWTUCMTKBV-UHFFFAOYSA-N 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
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 150000004992 toluidines Chemical class 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
- 239000005050 vinyl trichlorosilane Substances 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Dental Preparations (AREA)
- Graft Or Block Polymers (AREA)
Description
本発明は機械的性質の改善された歯科用材料に
関する。
本発明において「歯科用材料」なる語は、歯牙
窩洞を充填修復するための歯科用複合充填材料だ
けでなく、義歯床用材料、歯冠用材料、合着用材
料、歯列矯正用接着剤、窩洞塗布用接着剤および
歯牙裂溝封鎖材を包含する意味で使用される。
従来から用いられている歯冠用材料や義歯床材
料は、ポリメチルメタクリレートをラジカル重合
性単量体で溶解せしめた樹脂組成物が主に用いら
れている。しかしながらかかる樹脂組成物を用い
ると歯牙に比べて圧縮強度が不十分でかつ吸水後
の機械的強度の低下も顕著であることから、その
改善が望まれていた。
本発明者らは、かかる欠点を改善すべく鋭意検
討を行なつた結果、本発明に到達したもので本発
明の要旨とするところは、
(A) ジシクロペンテニル基を側鎖に有するビニル
系単量体とアクリル酸エステルおよび／または
メタクリル酸エステルとを共重合して得られる
アクリル樹脂、
(B) １分子中に少なくとも１個のアクリロイルオ
キシ基および／またはメタクリロイルオキシ基
を有する単量体、および
(C) 重合開始剤
よりなる歯科用材料、およびさらに必要により該
歯科用材料に充填材が添加されてなる歯科用材料
にある。
本発明の歯科用材料を構成するアクリル樹脂(A)
は、ジシクロペンテニル基を側鎖に有するビニル
系単量体とアクリル酸エステルおよび／またはメ
タクリル酸エステルとを通常のラジカル重合開始
剤、例えばアゾ系重合開始剤を用いて塊状、溶
液、懸濁または乳化重合によつて得た共重合体で
ある。本発明においてはアクリル樹脂(A)は、前記
の単量体からなる共重合体であれば使用できる
が、表面硬度、耐汚染性、耐水性および機械的強
度に優れた硬化物を与える歯科用材料を得るため
には、ジシクロペンテニル基を側鎖に有する単量
体0.5〜70重量％、好ましくは１〜50重量％およ
びアクリル酸エステルおよび／またはメタクリル
酸エステル99.5〜30重量％、好ましくは99〜50重
量％を共重合し、70℃以上のガラス転移温度およ
び60000以上の重量平均分子量をもつようにした
方がよい。アクリル樹脂(A)を構成するに使用され
るジシクロペンテニル基を側鎖に有する単量体の
例としては、アクリル酸ジシクロペンテニル、メ
タクリル酸ジシクロペンテニル、アクリル酸ジシ
クロペンテニルオキシエチルエステル、メタクリ
ル酸ジシクロペンテニルオキシエチルエステル、
等があげられる。これらは１種または１種以上が
使用される。
またアクリル樹脂(A)を構成するのに使用される
アクリル酸エステルおよび／またはメタクリル酸
エステルの例としては、アクリル酸メチル、メタ
クリル酸メチル、アクリル酸エチル、メタクリル
酸エチル、アクリル酸ｎ−ブチル、メタクリル酸
ｎ−ブチル、アクリル酸イソブチル、メタクリル
酸イソブチル、アクリル酸−２−エチルヘキシ
ル、メタクリル酸−２−エチルヘキシル等があげ
られる。これらは１種または１種以上が使用され
る。
本発明の歯科用材料をを構成するのに使用され
る単量体(B)は、重合開始剤により重合すると共に
前記のアクリル樹脂(A)中のジシクロペンテニル基
とのグラフトもしくは架橋反応を生起させて歯科
用材料として良好な硬化物を与えるための成分で
ある。この目的に使用される単量体の例として
は、前述のアクリル樹脂(A)を構成するに使用され
るアクリル酸エステルおよび／またはメタクリル
酸エステル、エチレングリコールジアクリレー
ト、エチレングリコールジメタクリレート、ジエ
チレングリコールジアクリレート、ジエチレング
リコールジメタクリレート、トリエチレングリコ
ールジアクリレート、トリエチレングリコールジ
メタクリレート、テトラエチレングリコールジア
クリレート、テトラエチレングリコールジメタク
リレート、１，３−ブタンジオールジアクリレー
ト、１，３−ブタンジオールジメタクリレート、
１，４−ブタンジオールジアクリレート、１，４
−ブタンジオールジメタクリレート、ネオペンチ
ルグリコールジアクリレート、ネオペンチルグリ
コールジメタクリレート、１，６−ヘキサンジオ
ールジアクリレート、１，６−ヘキサンジオール
ジメタクリレート、トリメチロールプロパントリ
アクリレート、トリメチロールプロパントリメタ
クリレート、ペンタエリスリトールトリアクリレ
ート、ペンタエリスリトールトリメタクリレー
ト、ペンタエリスリトールテトラアクリレート、
ペンタエリスリトールテトラメタクリレート等が
あげられる。これらは１種または２種以上が使用
できる。
また本発明の材料を構成する重合開始剤(C)とし
ては、過酸化ベンゾイル、過酸化アセチル、過酸
化ラウロイル、クメンヒドロパーオキシド、ｔ−
ブチルパーベンゾエート、ｔ−ブチルヒドロパー
オキシド等の有機過酸化物、２，2′−アゾビスイ
ソブチロニトリル等のアゾ化合物およびベンゾイ
ンアルキルエーテル、ベンゾフエノン、ジアセト
キシアセトフエノン等の光重合開始剤があげられ
る。これらの中でも特に有機過酸化物がアクリル
樹脂(A)と単量体(B)とのグラフトもしくは架橋反応
をを効果的に進めて、より高性能の硬化物を与え
るので好ましい。
本発明の材料中のアクリル樹脂(A)、単量体(B)お
よび重合開始剤(C)の組成割合は、使用する単量体
および重合開始剤の種類によつて一概に決められ
ないが、アクリル樹脂(A)および単量体(B)はアクリ
ル樹脂(A)および単量体(B)の合計量に対してそれぞ
れ30〜70重量％および70〜30重量％である。また
重合開始剤(C)はアクリル樹脂(A)および単量体(B)の
合計量100重量部に対して0.1〜10重量部である。
本発明の材料において、アクリル樹脂(A)の量が30
重量％未満では硬化時の重合収縮が大となり、か
つ圧縮強度の低下をきたし、また70重量％をこえ
る場合には得られる歯科材料の取扱いが困難とな
る。また重合開始剤の量が0.1重量部未満では重
合時間が長くなり、また10重量部をこえる場合に
は歯科材料の貯蔵安定性が悪くなる。
本発明の材料は、上述した三成分を必須成分と
して構成されるが、必要に応じて充填材を添加す
ることができる。添加することの出来る充填材の
例としては、例えばソーダガラス、バリウムガラ
ス、ストロンチユームガラス、石英、無定形シリ
カ、ホウケイ酸塩ガラス、アルミナアルミノシリ
ケート、ガラスセラミツクスなどの硬度が高く、
熱膨張係数が小さい無機質粉末、該無機質粉末の
表面を有機質重合体（例えばジメタクリレートポ
リマー）で被覆したいわゆる有機複合フイラーお
よび有機質重合体粉末（例えばポリメチルメタク
リレート）が挙げられる。かかる充填材の形状は
球状、小板片状、繊維状、ウイスカー状である
か、あるいはさらに不規則な形状であつてもよ
い。また無機質を充填材とする場合には適当な表
面処理をすることが好ましいく、かかる表面処理
方法としてはビニルトリクロロシラン、γ−メタ
クリロキシプロピルトリメトキシシランなどのシ
ランカツプリング剤による処理がある。充填材の
大きさとしては1000ミクロン以下、好ましくは
100ミクロン以下であり、充填材を加える量とし
ては単量体に対して18〜230％（体積）の範囲が
好ましい。
また、本発明の材料を口腔内で使用する場合硬
化するための促進剤、例えばナフテン酸コバルト
で代表される有機金属塩やＮ，N′−ジエタノー
ル−ｐ−トルイジン、トリエタノールアミンなど
のアミン化合物を使用することも可能である。
その他、本発明の材料には所望により紫外線吸
収剤、着色剤および重合禁止剤なども添加するこ
とができる。
以上述べたごとき構成成分からなる本発明の歯
科用材料は、従来の歯科用材料に比べて機械的強
度、圧縮強度および耐水性の良好な硬化物を形成
出来るために歯科用複合充填材、義歯床用材料、
歯冠用材料、合着用材料、歯列矯正用接着剤、窩
洞塗布用接着剤および歯牙裂溝封鎖材等の歯科用
材料として有用である。
以下、実施例により本発明を詳細に説明する
が、実施例中の「部」は「重量部」を表わす。
実施例 １
メタクリル酸メチル90部、メタクリル酸ジシク
ロペンテニル10部、およびアゾビスイソブチロニ
トリル0.5部の混合物を常法により85℃で懸濁重
合して、ガラス転移温度106℃、重量平均分子量
が128000のアクリル樹脂を得た。
次いで該アクリル樹脂100部にメタクリル酸メ
チル40部、エチレングリコールジメタクリレート
20部、およびベンゾイルパーオキシド３部を添加
し、40℃で均一になるまで混合撹拌して樹脂組成
物を得た。
次に、前装冠のエナメル層組成と類似させるた
めに前記樹脂組成物100部に、酸化チタン0.5部、
およびネーブルエロー赤口0.02部を加えよく混練
してペーストを得た。このペーストを金型に入れ
てオートクレーブ中4atmないし5atmの圧力およ
び120℃の温度で60分加熱硬化し試験片を作成し
た。
この試験片のプリネル表面硬度、圧縮強度、曲
げ強度、および吸水量測定結果を表１に示した。
この結果からも明確なように本発明の材料は歯冠
レジンやレジン歯として十分使用可能であること
がわかる。
比較例 １
実施例１の方法においてメタクリル酸ジシクロ
ペンテニルを使用しない条件で得たガラス転移温
度105℃、重量平均分子量72000のポリメチルメタ
クリレートをアクリル樹脂として用いる以外は実
施例１と全く同条件で、および方法をくり返して
試験片を作成し評価した。得られた評価結果も表
１に示した。
これらの結果からも明らかのようにジシクロペ
ンテニル基を含まないアクリル樹脂を用いた歯冠
用材料は本発明の材料と比べ圧縮強度、耐水性、
および表面硬度が劣ることがわかる。
The present invention relates to dental materials with improved mechanical properties. In the present invention, the term "dental material" refers not only to dental composite filling materials for filling and repairing tooth cavities, but also to denture base materials, dental crown materials, luting materials, orthodontic adhesives, The term is used to include adhesives for applying cavities and tooth fissure sealants. Conventionally used dental crown materials and denture base materials mainly include resin compositions in which polymethyl methacrylate is dissolved with a radically polymerizable monomer. However, when such a resin composition is used, its compressive strength is insufficient compared to that of a tooth, and the mechanical strength decreases significantly after water absorption, so an improvement has been desired. The present inventors have conducted intensive studies to improve these drawbacks, and as a result, they have arrived at the present invention, and the gist of the present invention is as follows: Acrylic resin obtained by copolymerizing a monomer with an acrylic ester and/or a methacrylic ester; (B) a monomer having at least one acryloyloxy group and/or methacryloyloxy group in one molecule; and (C) a dental material comprising a polymerization initiator, and a dental material further comprising a filler added to the dental material if necessary. Acrylic resin (A) constituting the dental material of the present invention
In this method, a vinyl monomer having a dicyclopentenyl group in the side chain and an acrylic ester and/or a methacrylic ester are combined into a lump, solution, or suspension using a conventional radical polymerization initiator, such as an azo polymerization initiator. Or it is a copolymer obtained by emulsion polymerization. In the present invention, the acrylic resin (A) can be used as long as it is a copolymer consisting of the above-mentioned monomers. To obtain the material, 0.5-70% by weight, preferably 1-50% by weight of monomers having dicyclopentenyl groups in their side chains and 99.5-30% by weight of acrylic esters and/or methacrylic esters, preferably It is preferable to copolymerize 99 to 50% by weight to have a glass transition temperature of 70° C. or higher and a weight average molecular weight of 60,000 or higher. Examples of monomers having a dicyclopentenyl group in the side chain used to constitute the acrylic resin (A) include dicyclopentenyl acrylate, dicyclopentenyl methacrylate, dicyclopentenyl acrylate oxyethyl ester, methacrylic acid dicyclopentenyloxyethyl ester,
etc. can be mentioned. One or more of these may be used. Examples of the acrylic ester and/or methacrylic ester used to constitute the acrylic resin (A) include methyl acrylate, methyl methacrylate, ethyl acrylate, ethyl methacrylate, n-butyl acrylate, Examples include n-butyl methacrylate, isobutyl acrylate, isobutyl methacrylate, 2-ethylhexyl acrylate, and 2-ethylhexyl methacrylate. One or more of these may be used. The monomer (B) used to constitute the dental material of the present invention is polymerized by a polymerization initiator and undergoes a grafting or crosslinking reaction with the dicyclopentenyl group in the acrylic resin (A). This component is used to give a cured product that is good as a dental material. Examples of monomers used for this purpose include acrylic esters and/or methacrylic esters used to constitute the above-mentioned acrylic resin (A), ethylene glycol diacrylate, ethylene glycol dimethacrylate, and diethylene glycol diacrylate. Acrylate, diethylene glycol dimethacrylate, triethylene glycol diacrylate, triethylene glycol dimethacrylate, tetraethylene glycol diacrylate, tetraethylene glycol dimethacrylate, 1,3-butanediol diacrylate, 1,3-butanediol dimethacrylate,
1,4-butanediol diacrylate, 1,4
-Butanediol dimethacrylate, neopentyl glycol diacrylate, neopentyl glycol dimethacrylate, 1,6-hexanediol diacrylate, 1,6-hexanediol dimethacrylate, trimethylolpropane triacrylate, trimethylolpropane trimethacrylate, pentaerythritol triacrylate, pentaerythritol trimethacrylate, pentaerythritol tetraacrylate,
Examples include pentaerythritol tetramethacrylate. These can be used alone or in combination of two or more. In addition, the polymerization initiator (C) constituting the material of the present invention includes benzoyl peroxide, acetyl peroxide, lauroyl peroxide, cumene hydroperoxide, t-
Organic peroxides such as butyl perbenzoate and t-butyl hydroperoxide, azo compounds such as 2,2'-azobisisobutyronitrile, and photopolymerization initiators such as benzoin alkyl ether, benzophenone, and diacetoxyacetophenone. can be given. Among these, organic peroxides are particularly preferred because they effectively promote the grafting or crosslinking reaction between the acrylic resin (A) and the monomer (B) to provide a cured product with higher performance. The composition ratios of the acrylic resin (A), monomer (B), and polymerization initiator (C) in the material of the present invention cannot be determined unconditionally depending on the types of monomers and polymerization initiator used. , acrylic resin (A) and monomer (B) are 30 to 70% by weight and 70 to 30% by weight, respectively, based on the total amount of acrylic resin (A) and monomer (B). The amount of the polymerization initiator (C) is 0.1 to 10 parts by weight based on 100 parts by weight of the total amount of the acrylic resin (A) and monomer (B).
In the material of the present invention, the amount of acrylic resin (A) is 30
If it is less than 70% by weight, polymerization shrinkage during curing will be large and the compressive strength will be reduced, and if it exceeds 70% by weight, the resulting dental material will be difficult to handle. Furthermore, if the amount of the polymerization initiator is less than 0.1 part by weight, the polymerization time will be prolonged, and if it exceeds 10 parts by weight, the storage stability of the dental material will be poor. The material of the present invention is composed of the above-mentioned three components as essential components, but a filler can be added as necessary. Examples of fillers that can be added include soda glass, barium glass, strontium glass, quartz, amorphous silica, borosilicate glass, alumina aluminosilicate, glass ceramics, etc. with high hardness;
Examples include inorganic powders with a small coefficient of thermal expansion, so-called organic composite fillers in which the surface of the inorganic powder is coated with an organic polymer (eg, dimethacrylate polymer), and organic polymer powders (eg, polymethyl methacrylate). The shape of such fillers may be spherical, platelet-like, fibrous, whisker-like, or even irregularly shaped. Further, when an inorganic filler is used, it is preferable to carry out a suitable surface treatment, and examples of such surface treatment include treatment with a silane coupling agent such as vinyltrichlorosilane or γ-methacryloxypropyltrimethoxysilane. The size of the filler is less than 1000 microns, preferably
It is 100 microns or less, and the amount of filler added is preferably in the range of 18 to 230% (volume) based on the monomer. In addition, when the material of the present invention is used in the oral cavity, an accelerator for curing, such as an organic metal salt represented by cobalt naphthenate, or an amine compound such as N,N'-diethanol-p-toluidine or triethanolamine. It is also possible to use In addition, ultraviolet absorbers, colorants, polymerization inhibitors, and the like can be added to the material of the present invention, if desired. The dental material of the present invention consisting of the above-mentioned components can form a cured product with better mechanical strength, compressive strength, and water resistance than conventional dental materials. flooring materials,
It is useful as dental materials such as dental crown materials, luting materials, orthodontic adhesives, cavity coating adhesives, and tooth fissure sealants. Hereinafter, the present invention will be explained in detail with reference to Examples, in which "parts" represent "parts by weight". Example 1 A mixture of 90 parts of methyl methacrylate, 10 parts of dicyclopentenyl methacrylate, and 0.5 parts of azobisisobutyronitrile was suspension polymerized at 85°C by a conventional method to obtain a glass transition temperature of 106°C and a weight average molecular weight. Obtained 128,000 acrylic resin. Next, 40 parts of methyl methacrylate and ethylene glycol dimethacrylate were added to 100 parts of the acrylic resin.
20 parts and 3 parts of benzoyl peroxide were added, and the mixture was mixed and stirred at 40°C until uniform, to obtain a resin composition. Next, 0.5 part of titanium oxide was added to 100 parts of the resin composition to make it similar to the enamel layer composition of the veneer.
and 0.02 part of Navel Yellow Akakuchi were added and kneaded well to obtain a paste. This paste was placed in a mold and cured by heating in an autoclave at a pressure of 4 atm to 5 atm and a temperature of 120° C. for 60 minutes to prepare a test piece. Table 1 shows the measurement results of Purinel surface hardness, compressive strength, bending strength, and water absorption of this test piece.
As is clear from these results, it can be seen that the material of the present invention can be sufficiently used as a dental crown resin or a resin tooth. Comparative Example 1 The same conditions as in Example 1 were used except that polymethyl methacrylate having a glass transition temperature of 105°C and a weight average molecular weight of 72,000, which was obtained in the method of Example 1 without using dicyclopentenyl methacrylate, was used as the acrylic resin. , and the method was repeated to prepare test pieces and evaluate them. The obtained evaluation results are also shown in Table 1. As is clear from these results, dental crown materials using acrylic resins that do not contain dicyclopentenyl groups have higher compressive strength, water resistance, and
It can be seen that the surface hardness is inferior.
【表】【table】
【表】
実施例 ２
メタクリル酸メチル70部、メタクリル酸ｎ−ブ
チル15部、アクリル酸ジシクロペンテニルオキシ
エチル15部、および２，2′−アゾビスイソブチロ
ニトリル0.5部からなる単量体混合物をを80℃で
６時間重合させて得たガラス転移温度80℃、重量
平均分子量156000のアクリル樹脂100部に、エチ
レングリコールジアクリレート40部、メタクリル
酸メチル20部およびＮ，Ｎ−ジメチル−ｐ−トル
イジン３部を加え混合溶解した。次いでこの溶解
物25部に、シラン被覆石英粉73部とアエロジル
＃380を1.5部加えてよく混練してユニバーサルペ
ーストを得た。一方、キヤタリストペーストは、
トリメチロールプロパントリメタクリレート５
部、トリエチレングリコールジメタクリレート10
部、前記アクリル樹脂５部、過酸化ベンゾイル
1.5部、シラン被覆石英粉72部、およびアエロジ
ル1.5部を混合、混練することにより得た。
次に上記のユニバーサルペーストおよびキヤタ
リストペーストを等量ずつ計り練和し、抜去した
歯牙窩洞に充填したところ、５分以内に硬化し
た。
かくして充填修復された歯牙の窩洞充填部分は
歯牙とよく調和していた。[Table] Example 2 Monomer mixture consisting of 70 parts of methyl methacrylate, 15 parts of n-butyl methacrylate, 15 parts of dicyclopentenyloxyethyl acrylate, and 0.5 part of 2,2'-azobisisobutyronitrile To 100 parts of an acrylic resin with a glass transition temperature of 80°C and a weight average molecular weight of 156,000 obtained by polymerizing at 80°C for 6 hours, 40 parts of ethylene glycol diacrylate, 20 parts of methyl methacrylate and N,N-dimethyl-p- 3 parts of toluidine was added and mixed and dissolved. Next, 73 parts of silane-coated quartz powder and 1.5 parts of Aerosil #380 were added to 25 parts of this melt and thoroughly kneaded to obtain a universal paste. On the other hand, catalyst paste is
Trimethylolpropane trimethacrylate 5
Part, triethylene glycol dimethacrylate 10
parts, 5 parts of the above acrylic resin, benzoyl peroxide
1.5 parts of quartz powder, 72 parts of silane-coated quartz powder, and 1.5 parts of Aerosil were mixed and kneaded. Next, equal amounts of the above-mentioned universal paste and catalyst paste were measured and kneaded, and when filled into the tooth cavity from which the tooth was extracted, it hardened within 5 minutes. The cavity filling portion of the tooth thus filled and restored was in good harmony with the tooth.
Claims (1)
ニル系単量体とアクリル酸エステルおよび／ま
たはメタクリル酸エステルとを共重合して得ら
れるアクリル樹脂， (B) １分子中に少なくとも１個のアクリロイルオ
キシ基および／またはメタクリロイルオキシ基
を有する単量体，および (c) 重合開始剤 よりなる歯科用材料。 ２ ジシクロペンテニル基を側鎖に有するビニル
系単量体がアクリル酸ジシクロペンテニル，メタ
クリル酸ジシクロペンテニル，アクリル酸ジシク
ロペンテニルオキシエステルおよびメタクリル酸
ジシクロペンテニルオキシエステルよりなる群か
ら選ばれる少なくとも１種であることを特徴とす
る特許請求の範囲第１項記載の歯科用材料。 ３ アクリル樹脂が70℃以上のガラス転移温度お
よび60000以上の重量平均分子量を有するもので
あることを特徴とする特許請求の範囲第１項記載
の歯科用材料。 ４ (A) ジシクロペンテニル基を側鎖に有するビ
ニル系単量体とアクリル酸エステルおよび／ま
たはメタクリル酸エステルとを共重合して得ら
れるアクリル樹脂， (B) １分子中に少なくとも１個のアクリロイルオ
キシ基および／またはメタアクリロイルオキシ
基を有する単量体， (C) 充填材，および (D) 重合開始剤 よりなる歯科用材料。 ５ ジシクロペンテニル基を側鎖に有するビニル
系単量体がアクリル酸ジシクロペンテニル，メタ
クリル酸ジシクロペンテニル，アクリル酸ジシク
ロペンテニルオキシエステルおよびメタクリル酸
ジシクロペンテニルオキシエステルよりなる群か
ら選ばれる少なくとも１種であることを特徴とす
る特許請求の範囲第４項記載の歯科用材料。 ６ アクリル樹脂が70℃以上のガラス転移温度お
よび60000以上の重量平均分子量を有するもので
あることを特徴とする特許請求の範囲第４項記載
の歯科用材料。 ７ 充填材が無機質粉末またはそれの有機複合フ
イラーであることを特徴とする特許請求の範囲第
４項記載の歯科用材料。[Scope of Claims] 1 (A) an acrylic resin obtained by copolymerizing a vinyl monomer having a dicyclopentenyl group in its side chain and an acrylic ester and/or a methacrylic ester, (B) one molecule A dental material comprising a monomer having at least one acryloyloxy group and/or methacryloyloxy group therein, and (c) a polymerization initiator. 2 At least the vinyl monomer having a dicyclopentenyl group in its side chain is selected from the group consisting of dicyclopentenyl acrylate, dicyclopentenyl methacrylate, dicyclopentenyl acrylate oxyester, and dicyclopentenyl methacrylate ester. The dental material according to claim 1, which is one type of dental material. 3. The dental material according to claim 1, wherein the acrylic resin has a glass transition temperature of 70° C. or higher and a weight average molecular weight of 60,000 or higher. 4 (A) Acrylic resin obtained by copolymerizing a vinyl monomer having a dicyclopentenyl group in the side chain and an acrylic ester and/or a methacrylic ester, (B) At least one acrylic resin in one molecule. A dental material comprising a monomer having an acryloyloxy group and/or a methacryloyloxy group, (C) a filler, and (D) a polymerization initiator. 5 At least the vinyl monomer having a dicyclopentenyl group in its side chain is selected from the group consisting of dicyclopentenyl acrylate, dicyclopentenyl methacrylate, dicyclopentenyl acrylate oxyester, and dicyclopentenyl methacrylate ester. 5. The dental material according to claim 4, which is one type of dental material. 6. The dental material according to claim 4, wherein the acrylic resin has a glass transition temperature of 70° C. or higher and a weight average molecular weight of 60,000 or higher. 7. The dental material according to claim 4, wherein the filler is an inorganic powder or an organic composite filler thereof.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58115711A JPS608214A (en) | 1983-06-27 | 1983-06-27 | Dental material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP58115711A JPS608214A (en) | 1983-06-27 | 1983-06-27 | Dental material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS608214A JPS608214A (en) | 1985-01-17 |
| JPH034041B2 true JPH034041B2 (en) | 1991-01-22 |
Family
ID=14669295
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP58115711A Granted JPS608214A (en) | 1983-06-27 | 1983-06-27 | Dental material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS608214A (en) |
Families Citing this family (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2621775B2 (en) * | 1993-12-15 | 1997-06-18 | タイガー魔法瓶株式会社 | Metal vacuum double container and method of manufacturing the same |
| JP5430095B2 (en) * | 2008-08-11 | 2014-02-26 | 日本カーバイド工業株式会社 | Curable resin composition |
| US10285913B2 (en) | 2014-02-25 | 2019-05-14 | Kuraray Noritake Dental Inc. | Dental polymerizable composition, dental temporary cement, dental filling material, denture liner, and dental tissue conditioner |
| EP3559958A1 (en) | 2016-12-21 | 2019-10-30 | 3M Innovative Properties Company | Conductive particles, articles, and methods |
| JP7066150B2 (en) * | 2018-03-30 | 2022-05-13 | 株式会社トクヤマデンタル | Manufacturing method of resin material for dental cutting |
-
1983
- 1983-06-27 JP JP58115711A patent/JPS608214A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS608214A (en) | 1985-01-17 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4308190A (en) | Dental materials based on organic plastics in paste form | |
| US4302376A (en) | Dental materials which are opaque to X-rays and are based on organic plastics in paste form | |
| KR102503905B1 (en) | Dental curable composition including chain transfer agent | |
| US4711913A (en) | Interpenetrating polymer network compositions employing rubber-modified polymers | |
| US4267097A (en) | Material for dental purposes | |
| US4396476A (en) | Blend of cross-linked polymer, swelling monomer and cross-linking agent and curing process | |
| CA2103400C (en) | Abrasion resistant dental composition product and process | |
| US4551486A (en) | Interpenetrating polymer network compositions | |
| US5210109A (en) | Interpenetrating polymer network compositions employing rubber-modified polymers | |
| US4369262A (en) | Dental material based on crosslinked plastic and polymerizable binder | |
| CA1173991A (en) | Hardenable polymeric prosthesis compositions | |
| AU556978B2 (en) | Stable one part dental compositions employing ipn technology | |
| US4394465A (en) | Dental materials based on organic plastics in paste form | |
| EP0142172A2 (en) | Composition usable as adhesive | |
| US4863977A (en) | Process for preparing interpenetrating polymer network objects employing rubber-modified polymers | |
| EP0166009A1 (en) | Photopolymerizable dental composition for preparing crowns and bridges | |
| JP2018123076A (en) | Dental-use curable composition having high mechanical strength | |
| JPH034041B2 (en) | ||
| JP4798680B2 (en) | Dental curable composition | |
| Watts | Orthodontic adhesive resins and composites: principles of adhesion | |
| JP3452613B2 (en) | Fluoride ion sustained release dental resin composition | |
| JPH0657716B2 (en) | Dental polymerization curable phosphazene compound | |
| JPS60152406A (en) | Dental material | |
| JPS61143310A (en) | Dental material | |
| JP3421072B2 (en) | Dental filling composition |