JPS6363605A - Photo-polymerizable dental material - Google Patents
Photo-polymerizable dental materialInfo
- Publication number
- JPS6363605A JPS6363605A JP61207785A JP20778586A JPS6363605A JP S6363605 A JPS6363605 A JP S6363605A JP 61207785 A JP61207785 A JP 61207785A JP 20778586 A JP20778586 A JP 20778586A JP S6363605 A JPS6363605 A JP S6363605A
- Authority
- JP
- Japan
- Prior art keywords
- reducing agent
- photo
- dental material
- photosensitizer
- polymerizable monomer
- 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
- 239000005548 dental material Substances 0.000 title claims abstract description 13
- 239000003638 chemical reducing agent Substances 0.000 claims abstract description 24
- 239000003504 photosensitizing agent Substances 0.000 claims abstract description 12
- 229930006711 bornane-2,3-dione Natural products 0.000 claims abstract description 11
- 239000000178 monomer Substances 0.000 claims abstract description 8
- NPKSPKHJBVJUKB-UHFFFAOYSA-N N-phenylglycine Chemical compound OC(=O)CNC1=CC=CC=C1 NPKSPKHJBVJUKB-UHFFFAOYSA-N 0.000 claims abstract description 7
- 125000005907 alkyl ester group Chemical group 0.000 claims abstract description 5
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 239000003054 catalyst Substances 0.000 claims description 4
- 125000002362 bornane-2,3-dione group Chemical group 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 3
- 239000000463 material Substances 0.000 abstract description 9
- VNQXSTWCDUXYEZ-UHFFFAOYSA-N 1,7,7-trimethylbicyclo[2.2.1]heptane-2,3-dione Chemical compound C1CC2(C)C(=O)C(=O)C1C2(C)C VNQXSTWCDUXYEZ-UHFFFAOYSA-N 0.000 abstract description 8
- 231100000252 nontoxic Toxicity 0.000 abstract description 4
- 230000003000 nontoxic effect Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 125000005396 acrylic acid ester group Chemical group 0.000 abstract 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 abstract 1
- 239000002685 polymerization catalyst Substances 0.000 abstract 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- -1 acrylic ester Chemical class 0.000 description 4
- 229920000298 Cellophane Polymers 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000005452 bending Methods 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 3
- 239000004810 polytetrafluoroethylene Substances 0.000 description 3
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 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
- 230000000052 comparative effect Effects 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 229910052698 phosphorus Inorganic materials 0.000 description 2
- 230000002165 photosensitisation Effects 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 210000000332 tooth crown Anatomy 0.000 description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- 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 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
- LBJBPGRQRGLKPL-UHFFFAOYSA-N 7-(4-chlorophenyl)-5-naphthalen-2-yl-6-sulfanylidene-2,3-dihydro-1h-pyrrolo[3,4-e][1,4]diazepin-8-one Chemical compound C1=CC(Cl)=CC=C1N1C(=S)C(C(=NCCN2)C=3C=C4C=CC=CC4=CC=3)=C2C1=O LBJBPGRQRGLKPL-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- QSJXEFYPDANLFS-UHFFFAOYSA-N Diacetyl Chemical group CC(=O)C(C)=O QSJXEFYPDANLFS-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 150000001413 amino acids Chemical class 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002872 contrast media Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 239000011350 dental composite resin Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- MLSGRWDEDYJNER-UHFFFAOYSA-N ethyl 2-anilinoacetate Chemical group CCOC(=O)CNC1=CC=CC=C1 MLSGRWDEDYJNER-UHFFFAOYSA-N 0.000 description 1
- 230000005281 excited state Effects 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000004922 lacquer Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- 239000004570 mortar (masonry) Substances 0.000 description 1
- GUAWMXYQZKVRCW-UHFFFAOYSA-N n,2-dimethylaniline Chemical compound CNC1=CC=CC=C1C GUAWMXYQZKVRCW-UHFFFAOYSA-N 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000000068 pit and fissure sealant Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000001603 reducing effect Effects 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 210000004885 white matter Anatomy 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
Landscapes
- Dental Preparations (AREA)
- Polymerisation Methods In General (AREA)
Abstract
Description
【発明の詳細な説明】
［産業上の利用分野］
本発明は、光重合性および機械的強度の優れた光重合性
歯科材料に関する。DETAILED DESCRIPTION OF THE INVENTION [Field of Industrial Application] The present invention relates to a photopolymerizable dental material with excellent photopolymerizability and mechanical strength.
［従来の技術およびその問題点］
光重合は、ラッカーおよび被覆塗装用樹脂の硬化、印刷
原版の製造および書類印刷への応用など多くの工業用途
に適用されている。BACKGROUND OF THE INVENTION Photopolymerization has been applied in many industrial applications, such as the curing of lacquer and coating resins, the production of printing plates and applications in document printing.
歯科領域においても、光重合性物質は歯牙充填材、歯牙
封止材あるいは歯冠部および樹脂製醤歯床の製造などに
応用されている。In the field of dentistry, photopolymerizable substances are also applied to the production of tooth filling materials, tooth sealing materials, tooth crowns, and resin dental bases.
ラジカル重合性単量体と光重合触媒とから成る光重合性
材料は、特公昭５４−１０９８６号公報に記載されてい
る。それによれば、光増感剤は下記の構造を有し、
（Ａは同じであっても異なっていてもよく、炭化水素基
またはＷ換炭化水素基であり、両方の基Ａが直接結合も
しくは二価の炭化水素基を介して一緒に結合していても
あるいは両方の基Ａが一緒になって縮合芳香族環系を形
成していてもよい）、例えば、ビアセチル、Ｐ、Ｐ’
−ジアルコキシベンジル、カンファーキノンなどが例
示されている。A photopolymerizable material comprising a radically polymerizable monomer and a photopolymerization catalyst is described in Japanese Patent Publication No. 10986/1986. According to it, a photosensitizer has the following structure, (A may be the same or different and is a hydrocarbon group or a W-substituted hydrocarbon group, and both groups A are directly bonded or (which may be linked together via a divalent hydrocarbon radical or both groups A together may form a fused aromatic ring system), for example biacetyl, P, P'
-Dialkoxybenzyl, camphorquinone, etc. are exemplified.
還元剤は下記の構造を有し、上記光増感剤が励起状態に
あるときに光増感剤を還元するものである。The reducing agent has the following structure and reduces the photosensitizer when the photosensitizer is in an excited state.
−Ｎ−Ｒ
（Ｒは同じであっても異なっていてもよく、水素、炭化
水素基、置換炭化水素基または２個のＲがＮと共に環系
を形成している基であり、３個のＲが同時に水素原子で
はなく、３個のＲが同時に置換炭化水素基ではなく、そ
してＮは芳香族基に対して直接に結合していない）、
具体σすとしては、プロピルアミン、ジメチルアミノエ
チルメタクリレート、Ｎ、Ｎ’ −ジメチルアニリン、
ピペリジンなどが挙げられている。しかし、還元剤とし
てこれらのアミンを使用した光重合性材料は、毒性の問
題で歯科材料としては不適である。-N-R (Rs may be the same or different, and are hydrogen, a hydrocarbon group, a substituted hydrocarbon group, or a group in which two Rs form a ring system together with N, and three R is not a hydrogen atom at the same time, three R's are not substituted hydrocarbon groups at the same time, and N is not directly bonded to an aromatic group), Examples include propylamine, dimethylaminoethyl methacrylate, N,N'-dimethylaniline,
Examples include piperidine. However, photopolymerizable materials using these amines as reducing agents are unsuitable as dental materials due to toxicity problems.
Ｅ間ａ点を解決する手段］
本発明は、短時間の光照射によって光重合が充分進行し
、硬度、硬化深度、曲げ強度、圧縮強度などの機械通強
度に優れ、且つ、毒性のない光重合性歯科材料に関する
。Means for Solving Point A between E and Point A] The present invention provides a non-toxic light irradiation system that allows photopolymerization to proceed sufficiently by short-time light irradiation, has excellent mechanical strength such as hardness, cure depth, bending strength, and compressive strength, and is non-toxic. Concerning polymerizable dental materials.
即ち、本発明は、ラジカル重合性Ｒｉ体と、光増感剤お
よび還元剤からなる光重合触媒とから成る光重合性歯科
材料であって、光増感剤がカンファーキノンであり、還
元剤が一般式［Ｉ］、（式中Ｒ１、Ｒ２は水素原子また
はアルキル基）で表されるＮ−フェニルグリシンおよび
そのアルキルエステルから選ばれた還元剤であることを
特徴とする光重合性歯科材料に関する。That is, the present invention provides a photopolymerizable dental material comprising a radically polymerizable Ri substance and a photopolymerization catalyst comprising a photosensitizer and a reducing agent, wherein the photosensitizer is camphorquinone and the reducing agent is camphorquinone. Relating to a photopolymerizable dental material characterized by being a reducing agent selected from N-phenylglycine and its alkyl ester represented by the general formula [I], (wherein R1 and R2 are hydrogen atoms or alkyl groups) .
ラジカル重合性単量体としては、アクリル酸エステル、
メタクリル酸エステル、−価または多価アルコールなど
のエチレン性不飽和化合物の他、ウレタン−アクリレー
ト共重合体、つＬノタンーメタクリレート共重合体ある
いはビスフェノールＡとグリシジルメタクリレートとの
反応生成物などが挙げられる。ラジカル重合性単量体は
１種類あるいは２種類以上を混合して使用できる。As the radically polymerizable monomer, acrylic ester,
In addition to ethylenically unsaturated compounds such as methacrylic esters and -hydric or polyhydric alcohols, examples include urethane-acrylate copolymers, L-notane-methacrylate copolymers, and reaction products of bisphenol A and glycidyl methacrylate. . The radically polymerizable monomers can be used alone or in combination of two or more.
光増感剤としては、カンファーキノンが使用される。カ
ンファーキノンはラジカル重合性Ｒ量体に対して０．０
０１〜１０Ｍ量％、好ましくは０．０５〜５重量％の割
合で使用される。Camphorquinone is used as a photosensitizer. Camphorquinone is 0.0 relative to radically polymerizable R-mer.
It is used in an amount of 0.01 to 10 M%, preferably 0.05 to 5% by weight.
カンファーキノンが０．００１重量％未満では、十分な
光増感効果が得られず、１０重量％を越える場合は、そ
れ以上光増感効果が向上せず、無意味であるばかりでな
く、得られた光重合性歯科材料の貯蔵安定性が低く好ま
しくない。If camphorquinone is less than 0.001% by weight, a sufficient photosensitizing effect cannot be obtained, and if it exceeds 10% by weight, the photosensitizing effect will not be improved any further, and it will not only be meaningless but also result in a loss of benefits. The storage stability of the photopolymerizable dental material obtained is undesirable.
還元剤としては、次式［Ｉ］、
（式中Ｒ，Ｒは水素原子またはアルキル基）で表される
Ｎ−フェニルグリシンおよびそのアルキルエステルから
選ばれた少なくとも１種の還元剤が使用される。具体通
にはＮ−フェニルグリシン、Ｎ−フェニルグリシンメチ
ル、Ｎ−フェニルグリシンエチルなどが挙げられる。こ
れらはほとんどすべての動物性■白質に含有されるアミ
ノ酸の１種であ２つ、還元剤として有用であると共に、
人体に全（無害である。As the reducing agent, at least one reducing agent selected from N-phenylglycine and its alkyl ester represented by the following formula [I], (wherein R and R are hydrogen atoms or alkyl groups) is used. . Specific examples include N-phenylglycine, N-phenylglycinemethyl, and N-phenylglycineethyl. These are two types of amino acids contained in almost all animal white matter, and are useful as reducing agents.
Totally harmless to the human body.
還元剤はラジカル重合性単量体に対して０．００１〜１
０重量％、好ましくは０．０５〜５Ｍ量％の割合で使用
される。The reducing agent is 0.001 to 1 for the radically polymerizable monomer.
It is used in a proportion of 0% by weight, preferably 0.05-5M%.
還元剤が０．００１重量％未満では、十分な還元効果が
得られず、１０Ｍ量％を越える場合は、得られた光重、
合性歯科材料の貯蔵安定性が低（好ましくない。If the reducing agent is less than 0.001% by weight, a sufficient reducing effect cannot be obtained, and if it exceeds 10M%, the resulting light weight,
Low storage stability of synthetic dental materials (unfavorable).
本発明の光重合性歯科材料には、慣用されている添加剤
、例えば、貯蔵安定性を維持するための安定剤、Ｘ線造
影剤、顔料などを添加できる。The photopolymerizable dental material of the present invention may contain commonly used additives, such as stabilizers for maintaining storage stability, X-ray contrast agents, pigments, and the like.
本発明の光重合性歯科材料は、従来の光重合性材料と同
様に、ハロゲンランプ、キセノンランプ、螢光灯あるい
は太陽光などを光源とする光によって光重合することが
できる。The photopolymerizable dental material of the present invention, like conventional photopolymerizable materials, can be photopolymerized by light from a halogen lamp, xenon lamp, fluorescent lamp, sunlight, or the like as a light source.
以下に実施例により本発明の詳細な説明する。The present invention will be explained in detail below using examples.
実施例
暗室中で２，２−ビス［’４−（３−メタクリロキシ−
２−ヒドロキシプロポキシ）−フェニル〕プロパン７０
重量部とトリエチレングリコールジメタクリレート３０
重量部とを混合し、この混合液にカンファーキノンを０
．２ｆｆｉｆｆｉ％添加して光増感剤を調整した。この
調整液をビーカーに分取し、各にのビーカーに第１表に
示した割合でＮ−フェニルグリシンを添加し、光増感剤
−還元剤系の光重合性材料を調整した。Example In a dark room, 2,2-bis['4-(3-methacryloxy-
2-Hydroxypropoxy)-phenyl]propane 70
Part by weight and triethylene glycol dimethacrylate 30
Part by weight, and add 0 camphorquinone to this mixed solution.
．． A photosensitizer was prepared by adding 2ffiffi%. This adjusted solution was divided into beakers, and N-phenylglycine was added to each beaker in the proportions shown in Table 1 to prepare a photosensitizer-reducing agent type photopolymerizable material.
上記の如く調整した各々の光重合性材料１８部に、Ｔ−
メタクリロキシプロピルトリメトキシシランで表面処理
をした石英粉［■龍森裂： ＣＲ５２１０７０５］８２
Ｂを添加し、メノウ乳鉢中で練和してペースト状とした
。To 18 parts of each photopolymerizable material prepared as above, T-
Quartz powder surface treated with methacryloxypropyltrimethoxysilane [■Tatsumori: CR5210705] 82
B was added and kneaded in an agate mortar to form a paste.
上記ペーストを用いて各物性を以下の如くにして測定し
た。Using the above paste, various physical properties were measured as follows.
［硬化深度］
厚さ１０鶴のポリテトラフルオロエチレン製シートに、
直径４１ｍの貫通孔を設け、この孔に前記ペーストを充
填した。その表面をセロファンで覆い、歯科充填樹脂重
合用の可視光線照射装置ｆ（Ｋｕｌｚｅｒ社製、トラン
スラックス）により３０秒間光を照射した。次いで、孔
から光照射面から重合の進んだペースト（円柱形）を取
り出し、カッターナイフで未重合部分を除去した後の長
さを測定し、硬化深度とする。[Curing depth] A polytetrafluoroethylene sheet with a thickness of 10 mm,
A through hole with a diameter of 41 m was provided, and the hole was filled with the paste. The surface was covered with cellophane and irradiated with light for 30 seconds using a visible light irradiation device f (manufactured by Kulzer, Translux) for polymerizing dental filling resins. Next, the polymerized paste (cylindrical shape) is taken out from the light-irradiated surface through the hole, and the length after removing the unpolymerized portion with a cutter knife is measured and determined as the hardening depth.
［ブリネル硬度、圧縮強度］
厚さ５Ｒのポリテトラフルオロエチレン製シートに、直
径４寵の貫通孔を設け、シートの片面にガラス板を当て
、反対面からこの孔に前記ペーストを充填した。その表
面をセロファンで覆い、上記照射装置により３０秒間光
を照射した。次いで、シートを裏返し、ガラス面側から
も３０秒間光を照射した。孔から重合生成物（円柱形）
を取り出し、ブリネル硬度と圧縮強度をご１定した。測
定はそれぞれＪＩＳ Ｔ６５０６およびＡＤＡ規格Ｎ
００２７に準拠して行った。[Brinell Hardness, Compressive Strength] A 5R thick polytetrafluoroethylene sheet was provided with four through holes in diameter, a glass plate was placed on one side of the sheet, and the paste was filled into the holes from the opposite side. The surface was covered with cellophane and irradiated with light for 30 seconds using the above irradiation device. Next, the sheet was turned over and irradiated with light for 30 seconds from the glass side as well. Polymerization product (cylindrical shape) from the pores
was taken out, and its Brinell hardness and compressive strength were determined. Measurements are based on JIS T6506 and ADA standard N.
The test was carried out in accordance with 0027.
［曲げ強度〕
厚さ２ｎのポリテトラフルオロエチレン製シートに、巾
２日、長さ２５１ｍの方形の孔を設け、シートの片面に
ガラス板を当て、反対面からこの孔に前記ペーストを充
填した。その表面をセロファンで覆い、歯冠用硬質樹脂
重合用の可視光線照射装２（Ｋｕｌｚｅｒ社製、デンタ
カラーＸＳ）に−より９０秒間光を照射した０次いで、
孔から重合生成物（２Ｘ２５Ｘ２ｍｍの方形）を取り出
し、ＩＳＯ規格４０４９に準拠して曲げ強度をヨＩＪ定
した。[Bending strength] A rectangular hole with a width of 2 days and a length of 251 m was provided in a polytetrafluoroethylene sheet with a thickness of 2 nm, a glass plate was placed on one side of the sheet, and the hole was filled with the paste from the other side. . The surface was covered with cellophane and irradiated with light for 90 seconds using a visible light irradiation device 2 (manufactured by Kulzer, Dentacolor XS) for polymerizing hard resins for dental crowns.
The polymerization product (2 x 25 x 2 mm square) was taken out from the hole, and the bending strength was determined according to ISO standard 4049.
以上の測定結果を第１表に示す。The above measurement results are shown in Table 1.
比較例
実施例と同様にして光増感剤を調整し、第１表に示した
割合で各種還元剤を添加し、光増感剤−還元剤系の光重
合性材料を調整した。以下実施例と同様の操作によって
ペーストを調整し、それらを用いて物性の測定を行った
。結果を第１表に示す。還元剤を添加していない比較例
１では、表層の僅か１ｕ厚さを除いて架橋しておらず、
物性の測定ができなかった。Comparative Example A photosensitizer was prepared in the same manner as in the example, and various reducing agents were added in the proportions shown in Table 1 to prepare a photosensitizer-reducing agent type photopolymerizable material. Pastes were prepared in the same manner as in the examples, and their physical properties were measured using them. The results are shown in Table 1. In Comparative Example 1, in which no reducing agent was added, there was no crosslinking except for the surface layer, which was only 1 μ thick.
Physical properties could not be measured.
［発明の効果］
本発明の光重合性材料の光重合触媒を構成する還元剤は
、従来のアミン系還元剤に比較して、少量の添加で優れ
た光重合性が得られ、また、得られた重合物の硬度、機
械的強度なども優れている。[Effects of the Invention] Compared to conventional amine-based reducing agents, the reducing agent constituting the photopolymerization catalyst of the photopolymerizable material of the present invention can provide excellent photopolymerizability even when added in a small amount. The hardness and mechanical strength of the resulting polymer are also excellent.
従って、歯科用コンポシフト樹脂、歯牙封止材、歯冠部
および樹脂製袋歯床など歯科分野に広く用いることがで
きる。さらに、アミン系還元剤は人体に毒性を有するが
、本発明の還元剤は人体に無毒な還元剤である。Therefore, it can be widely used in the dental field, such as dental composite shift resins, tooth sealants, tooth crowns, and resin-made tooth bases. Furthermore, while amine reducing agents are toxic to the human body, the reducing agent of the present invention is non-toxic to the human body.
Claims (1)
る光重合触媒とから成る光重合性歯科材料であって、光
増感剤がカンファーキノンであり、還元剤が一般式［
I ］、 ▲数式、化学式、表等があります▼［ I ］ （式中Ｒ＿１、Ｒ＿２は水素原子またはアルキル基）で
表されるＮ−フェニルグリシンおよびそのアルキルエス
テルから選ばれた還元剤であることを特徴とする光重合
性歯科材料。[Scope of Claims] A photopolymerizable dental material comprising a radically polymerizable monomer and a photopolymerization catalyst comprising a photosensitizer and a reducing agent, wherein the photosensitizer is camphorquinone and the reducing agent is is the general formula [
I], ▲Mathematical formulas, chemical formulas, tables, etc. are available▼[I] (In the formula, R_1 and R_2 are hydrogen atoms or alkyl groups) A reducing agent selected from N-phenylglycine and its alkyl esters A photopolymerizable dental material characterized by:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61207785A JPH06689B2 (en) | 1986-09-05 | 1986-09-05 | Photopolymerizable dental material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP61207785A JPH06689B2 (en) | 1986-09-05 | 1986-09-05 | Photopolymerizable dental material |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6363605A true JPS6363605A (en) | 1988-03-22 |
| JPH06689B2 JPH06689B2 (en) | 1994-01-05 |
Family
ID=16545464
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP61207785A Expired - Lifetime JPH06689B2 (en) | 1986-09-05 | 1986-09-05 | Photopolymerizable dental material |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH06689B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530038A (en) * | 1993-08-02 | 1996-06-25 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| JPH1135415A (en) * | 1997-07-22 | 1999-02-09 | Kuraray Co Ltd | Photopolymerizable composition for dental use |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4884183A (en) * | 1972-01-25 | 1973-11-08 | ||
| JPS5410986A (en) * | 1977-06-25 | 1979-01-26 | Yoshimi Takada | Connection cable having independant shield skin |
| JPS564604A (en) * | 1979-06-18 | 1981-01-19 | Eastman Kodak Co | Coinitiating agent composition |
| JPS60502055A (en) * | 1983-07-25 | 1985-11-28 | アメリカン デンタル アソシエイシヨン ヘルス フアウンデイシヨン | Tooth surface treatment products |
| JPS61144641A (en) * | 1984-12-18 | 1986-07-02 | Hitachi Chem Co Ltd | Photopolymerizable composition |
-
1986
- 1986-09-05 JP JP61207785A patent/JPH06689B2/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4884183A (en) * | 1972-01-25 | 1973-11-08 | ||
| JPS5410986A (en) * | 1977-06-25 | 1979-01-26 | Yoshimi Takada | Connection cable having independant shield skin |
| JPS564604A (en) * | 1979-06-18 | 1981-01-19 | Eastman Kodak Co | Coinitiating agent composition |
| JPS60502055A (en) * | 1983-07-25 | 1985-11-28 | アメリカン デンタル アソシエイシヨン ヘルス フアウンデイシヨン | Tooth surface treatment products |
| JPS61144641A (en) * | 1984-12-18 | 1986-07-02 | Hitachi Chem Co Ltd | Photopolymerizable composition |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5530038A (en) * | 1993-08-02 | 1996-06-25 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| US5587406A (en) * | 1993-08-02 | 1996-12-24 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| US5834532A (en) * | 1993-08-02 | 1998-11-10 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| US6071983A (en) * | 1993-08-02 | 2000-06-06 | Sun Medical Co., Ltd. | Primer composition and curable composition |
| JPH1135415A (en) * | 1997-07-22 | 1999-02-09 | Kuraray Co Ltd | Photopolymerizable composition for dental use |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH06689B2 (en) | 1994-01-05 |
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