JP6076475B2 - 重合性混合組成物、該混合組成物の用途、及び歯科補綴物 - Google Patents
重合性混合組成物、該混合組成物の用途、及び歯科補綴物 Download PDFInfo
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- 239000000178 monomer Substances 0.000 claims description 32
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- 239000007787 solid Substances 0.000 claims description 26
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- 229920003229 poly(methyl methacrylate) Polymers 0.000 claims description 23
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- -1 polydimethylsiloxane Polymers 0.000 claims description 21
- 239000004205 dimethyl polysiloxane Substances 0.000 claims description 17
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims description 17
- 229920003023 plastic Polymers 0.000 claims description 13
- 239000004033 plastic Substances 0.000 claims description 13
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 12
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- 239000012141 concentrate Substances 0.000 description 6
- 229940120693 copper naphthenate Drugs 0.000 description 6
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 6
- WLCFKPHMRNPAFZ-UHFFFAOYSA-M didodecyl(dimethyl)azanium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+](C)(C)CCCCCCCCCCCC WLCFKPHMRNPAFZ-UHFFFAOYSA-M 0.000 description 6
- 239000012456 homogeneous solution Substances 0.000 description 6
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- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 5
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- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
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- HSOOIVBINKDISP-UHFFFAOYSA-N 1-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(CCC)OC(=O)C(C)=C HSOOIVBINKDISP-UHFFFAOYSA-N 0.000 description 1
- KCWWCWMGJOWTMY-UHFFFAOYSA-N 1-benzyl-5-phenyl-1,3-diazinane-2,4,6-trione Chemical compound O=C1C(C=2C=CC=CC=2)C(=O)NC(=O)N1CC1=CC=CC=C1 KCWWCWMGJOWTMY-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical group C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 238000004566 IR spectroscopy Methods 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 229910002808 Si–O–Si Inorganic materials 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
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- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
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- 238000001746 injection moulding Methods 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 239000011344 liquid material Substances 0.000 description 1
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- 125000005395 methacrylic acid group Chemical group 0.000 description 1
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- 125000005375 organosiloxane group Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 230000037361 pathway Effects 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- 239000010420 shell particle Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
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- 150000003573 thiols Chemical class 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-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
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
- C08F265/04—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00 on to polymers of esters
- C08F265/06—Polymerisation of acrylate or methacrylate esters on to polymers thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/887—Compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/80—Preparations for artificial teeth, for filling teeth or for capping teeth
- A61K6/884—Preparations for artificial teeth, for filling teeth or for capping teeth comprising natural or synthetic resins
- A61K6/891—Compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- A61K6/896—Polyorganosilicon compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
- C08F283/124—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes on to polysiloxanes having carbon-to-carbon double bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
- C08F290/068—Polysiloxanes
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- Health & Medical Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Life Sciences & Earth Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- Epidemiology (AREA)
- Plastic & Reconstructive Surgery (AREA)
- Dental Preparations (AREA)
- Dermatology (AREA)
- Transplantation (AREA)
- Dentistry (AREA)
Description
97gのMW134(ポリメタクリル酸メチルコポリマー、Evonik社製)及び3gの1−ベンジル−5−フェニル−バルビツール酸。
95.6gのメタクリル酸メチル、4gの1,4−ブタンジオールジメタクリレート、0.2gのジラウリルジメチルアンモニウムクロライド、及び0.2gのナフテン酸銅濃縮物を合わせ、塩化物が溶解した後に、澄みきった均一溶液を形成する。
93.6gのメタクリル酸メチル、4gの1,4−ブタンジオールジメタクリレート、2gの液体MA−15M、0.2gのジラウリルジメチルアンモニウムクロライド、及び0.2gのナフテン酸銅濃縮物を合わせ、塩化物が溶解した後に、澄みきった均一溶液を形成する。液体MA−15Mは、平均鎖長n=15と片側末端メタクリル基とを有する、直鎖ポリジメチルシロキサンの透明な薄い液体である(図2.1参照)。
80.6gのメタクリル酸メチル、4gの1,4−ブタンジオールジメタクリレート、15gの液体MA−15M、0.2gのジラウリルジメチルアンモニウムクロライド、及び0.2gのナフテン酸銅濃縮物を合わせ、塩化物が溶解した後に、澄みきった均一溶液を形成する。
90.6gのメタクリル酸メチル、4gの1,4−ブタンジオールジメタクリレート、5gのW35、0.2gのジラウリルジメチルアンモニウムクロライド、及び0.2gのナフテン酸銅濃縮物を合わせ、塩化物及びW35が溶解した後に、澄みきった均一溶液を形成する。W35は、平均鎖長n=40と、ポリカプロラクトンで修飾されている鎖末端(平均鎖長y=15/側)とを有する、直鎖ポリジメチルシロキサンである。それはワックス状構造を有するが、MMA及び後者のコモノマー中に良好に溶解する(図2.3参照)。
85.4gのメタクリル酸メチル、4gのブタンジオールジメタクリレート、10gの液体MA−40D、0.2gのジラウリルジメチルアンモニウムクロライド、及び0.2gのナフテン酸銅濃縮物を合わせ、塩化物が溶解した後に、澄みきった均一溶液を形成する。液体MA−40Dは、平均鎖長n=40と、両側に、それぞれがメタクリル基をもつ末端基修飾とを有する、直鎖ポリジメチルシロキサンの透明な薄い液体である(図2.2参照)
91.6gのメタクリル酸メチル、4gの1,4−ブタンジオールジメタクリレート、4gのMD−M−2520Mu、0.2gのジラウリルジメチルアンモニウムクロライド、0.2gのナフテン酸銅濃縮物を合わせ、塩化物が溶解した後に、澄みきった均一溶液を形成する。MD−M−2520Muは、平均鎖長n=35と、両側に多重にアクリル化された鎖末端とを有する、直鎖PDMSの透明な液体である(図2.8参照)。
20gのポリマー成分Bを、14mlのモノマー成分Aと混合し、長方形のモールドに注入し、歯科用プレッシャーポット中で、2バール及び50℃において、15分間重合させる。標準混合物のシートは、ほぼ澄みきっているのに対し、改質されたシートは、透明であるが均一な乳白性があり、後者は、材料が市販の歯科用の色に調整され得る程度の強さである。
Claims (10)
- 破壊靱性と破断エネルギーの増大した歯科用インプラント又は補綴物を作製するための、少なくとも1つのモノマー部分としてメタクリル酸メチル(MMA)を有する液体若しくは半固体成分Aと、ポリメタクリル酸メチル(PMMA)ベースの、フィラー及び/又は添加剤を有する固体成分Bとを含有する重合性混合組成物であって、前記液体若しくは半固体成分Aが付加的に、前記モノマー部分を改質しかつ前記モノマー部分と混和性である、ポリジメチルシロキサン(PDMS)、ポリジフェニルシロキサン(PDPS)、ポリメチルフェニルシロキサン(PMPS)、及び/又はそれらの混合物からなる群より選択される少なくとも1つのオリゴマー若しくはポリマーポリオルガノシロキサンを有し、重合した混合組成物が破壊靱性(K max )≧1.9kJm 1/2 と破断エネルギー≧900J/m 2 とを有する、該重合性混合組成物。
- 前記固体成分B及び前記液体若しくは半固体成分Aが、開始剤成分を含有することを特徴とする、請求項1に記載の重合性混合組成物。
- 前記液体または半固体成分A中の、オリゴマー若しくはポリマー化合物の部分が、0.1〜50重量%の範囲内になることを特徴とする、請求項1又は2に記載の重合性混合組成物。
- 前記ポリオルガノシロキサンが、前記液体若しくは半固体成分Aのモノマー部分と均一混和性である、及び/又は好ましくは直鎖構造を有することを特徴とする、請求項1に記載の重合性混合組成物。
- 直鎖ポリオルガノシロキサン基の平均数(n)が、2〜500の範囲内になることを特徴とする、請求項4に記載の重合性混合組成物。
- 前記ポリオルガノシロキサン鎖の構造が化学的に修飾されることを特徴とする、請求項4又は5に記載の重合性混合組成物。
- 前記ポリオルガノシロキサン鎖の構造が、置換基により、化学的に修飾されることを特徴とする、請求項6に記載の重合性混合組成物。
- 請求項1から7のいずれか1項に記載の重合性混合組成物の、プラスチックモールド製造のための使用。
- 前記重合性混合組成物が、このタイプのモールドなどのための修復材料として使用されることを特徴とする、請求項8に記載の使用。
- 請求項1〜7の少なくとも1項に記載の重合性混合組成物を用いて作製された歯科補綴物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE102012013514.9 | 2012-07-06 | ||
DE102012013514.9A DE102012013514A1 (de) | 2012-07-06 | 2012-07-06 | Polymerisierbare Mischungszusammensetzung, Verwendung der Mischungszusammensetzung sowie eine Dentalprothese |
PCT/EP2013/002010 WO2014005727A1 (de) | 2012-07-06 | 2013-07-08 | Polymerisierbare mischungszusammensetzung, verwendung der mischungszusammensetzung sowie eine dentalprothese |
Publications (2)
Publication Number | Publication Date |
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JP2015522571A JP2015522571A (ja) | 2015-08-06 |
JP6076475B2 true JP6076475B2 (ja) | 2017-02-08 |
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Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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JP2015518899A Active JP6076475B2 (ja) | 2012-07-06 | 2013-07-08 | 重合性混合組成物、該混合組成物の用途、及び歯科補綴物 |
Country Status (10)
Country | Link |
---|---|
US (1) | US20150305987A1 (ja) |
EP (1) | EP2869855B1 (ja) |
JP (1) | JP6076475B2 (ja) |
KR (1) | KR20150065659A (ja) |
CA (1) | CA2881476C (ja) |
DE (1) | DE102012013514A1 (ja) |
ES (1) | ES2848535T3 (ja) |
PT (1) | PT2869855T (ja) |
RU (1) | RU2015104000A (ja) |
WO (1) | WO2014005727A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR101931454B1 (ko) | 2017-12-29 | 2018-12-20 | 박성원 | 광경화성 조성물 및 이를 이용하여 제조된 성형품 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102014109233A1 (de) * | 2014-07-01 | 2016-01-07 | Heraeus Kulzer Gmbh | Fräsrohlinge basierend auf polymerisiertem Prothesenmaterial, insbesondere einem auspolymerisierten, bruchzähen Prothesenmaterial, in Form von Fräsrohlingen |
EP3375429A1 (de) * | 2017-03-17 | 2018-09-19 | Ivoclar Vivadent AG | Monochromatischer dentaler formkörper und rohling zur herstellung von dentalrestaurationen |
CN107596441A (zh) * | 2017-10-09 | 2018-01-19 | 南京图艾生物医药科技有限公司 | 一种改性聚甲基丙烯酸甲酯软质假肢材料 |
KR102020131B1 (ko) * | 2017-12-29 | 2019-09-09 | 박성원 | 광경화성 조성물 및 이를 이용하여 제조된 성형품 |
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FR2178329A5 (ja) * | 1972-03-28 | 1973-11-09 | Rhone Poulenc Sa | |
JPS61227509A (ja) * | 1985-04-02 | 1986-10-09 | G C Dental Ind Corp | 歯科用修復材 |
DE19617876A1 (de) * | 1996-04-24 | 1997-11-06 | Ivoclar Ag | Polymerisierbares Dentalmaterial |
JP3478521B2 (ja) * | 1997-02-17 | 2003-12-15 | 株式会社トクヤマ | 歯科用軟質裏装材 |
DE19816148A1 (de) * | 1998-04-09 | 1999-10-21 | Wacker Chemie Gmbh | Organopolysiloxanpartikel enthaltende acrylathaltige Zusammensetzung |
JP2003507499A (ja) * | 1999-08-13 | 2003-02-25 | デルタメド・メディツィーンプロドュクテ・ゲゼルシャフト・ミット・ベシュレンクテル・ハフツング | 可視光を用いて架橋する組成物およびその使用 |
DE102005012825B4 (de) | 2005-03-17 | 2009-05-07 | Heraeus Kulzer Gmbh | Hochschlagzähe (High Impact) Prothesenkunststoffe und ihre Verwendung |
JP5184113B2 (ja) * | 2008-01-31 | 2013-04-17 | ポーラ化成工業株式会社 | ポイントメークアップ化粧料 |
JP5750231B2 (ja) * | 2010-03-30 | 2015-07-15 | 富士フイルム株式会社 | 塗布組成物、光学フィルム、偏光板、及び画像表示装置 |
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EP2869855A1 (de) | 2015-05-13 |
KR20150065659A (ko) | 2015-06-15 |
CA2881476A1 (en) | 2014-01-09 |
DE102012013514A1 (de) | 2014-05-22 |
PT2869855T (pt) | 2020-11-25 |
EP2869855B1 (de) | 2020-11-04 |
WO2014005727A1 (de) | 2014-01-09 |
JP2015522571A (ja) | 2015-08-06 |
CA2881476C (en) | 2018-01-02 |
RU2015104000A (ru) | 2016-08-27 |
US20150305987A1 (en) | 2015-10-29 |
ES2848535T3 (es) | 2021-08-10 |
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