JP5931057B2 - 歯科材料、歯科材料組成物、歯科修復材料および硬化物 - Google Patents
歯科材料、歯科材料組成物、歯科修復材料および硬化物 Download PDFInfo
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- JP5931057B2 JP5931057B2 JP2013515124A JP2013515124A JP5931057B2 JP 5931057 B2 JP5931057 B2 JP 5931057B2 JP 2013515124 A JP2013515124 A JP 2013515124A JP 2013515124 A JP2013515124 A JP 2013515124A JP 5931057 B2 JP5931057 B2 JP 5931057B2
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- Prior art keywords
- meth
- dental
- urethane
- dental material
- reaction
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- 239000005548 dental material Substances 0.000 title claims description 102
- 239000000203 mixture Substances 0.000 title claims description 60
- 239000000463 material Substances 0.000 title claims description 40
- 239000000178 monomer Substances 0.000 claims description 71
- 150000001875 compounds Chemical class 0.000 claims description 28
- 239000000945 filler Substances 0.000 claims description 25
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 239000003505 polymerization initiator Substances 0.000 claims description 12
- 239000003999 initiator Substances 0.000 claims description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 8
- -1 acryl compound Chemical class 0.000 description 167
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 88
- 238000006116 polymerization reaction Methods 0.000 description 73
- 238000006243 chemical reaction Methods 0.000 description 62
- 238000004519 manufacturing process Methods 0.000 description 59
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 34
- 238000001157 Fourier transform infrared spectrum Methods 0.000 description 31
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 27
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 27
- 238000001723 curing Methods 0.000 description 22
- 239000000047 product Substances 0.000 description 19
- 238000000034 method Methods 0.000 description 17
- 239000003054 catalyst Substances 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 15
- 239000011350 dental composite resin Substances 0.000 description 13
- 239000003112 inhibitor Substances 0.000 description 13
- 125000000962 organic group Chemical group 0.000 description 13
- 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 12
- 239000011256 inorganic filler Substances 0.000 description 11
- 229910003475 inorganic filler Inorganic materials 0.000 description 11
- 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 10
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- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 9
- 239000003638 chemical reducing agent Substances 0.000 description 9
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- 230000018044 dehydration Effects 0.000 description 9
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- 238000005259 measurement Methods 0.000 description 8
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- 238000003756 stirring Methods 0.000 description 7
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
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- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- KORSJDCBLAPZEQ-UHFFFAOYSA-N dicyclohexylmethane-4,4'-diisocyanate Chemical compound C1CC(N=C=O)CCC1CC1CCC(N=C=O)CC1 KORSJDCBLAPZEQ-UHFFFAOYSA-N 0.000 description 6
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 5
- UEKHZPDUBLCUHN-UHFFFAOYSA-N 2-[[3,5,5-trimethyl-6-[2-(2-methylprop-2-enoyloxy)ethoxycarbonylamino]hexyl]carbamoyloxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOC(=O)NCCC(C)CC(C)(C)CNC(=O)OCCOC(=O)C(C)=C UEKHZPDUBLCUHN-UHFFFAOYSA-N 0.000 description 5
- MCMNRKCIXSYSNV-UHFFFAOYSA-N ZrO2 Inorganic materials O=[Zr]=O MCMNRKCIXSYSNV-UHFFFAOYSA-N 0.000 description 5
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- 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 description 4
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- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 238000005299 abrasion Methods 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
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- 125000005442 diisocyanate group Chemical group 0.000 description 4
- 239000002245 particle Substances 0.000 description 4
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 239000004593 Epoxy Substances 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 229910052788 barium Inorganic materials 0.000 description 3
- DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 description 3
- 208000002925 dental caries Diseases 0.000 description 3
- 239000003479 dental cement Substances 0.000 description 3
- 230000001877 deodorizing effect Effects 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical group [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 3
- 238000007599 discharging Methods 0.000 description 3
- ORBFAMHUKZLWSD-UHFFFAOYSA-N ethyl 2-(dimethylamino)benzoate Chemical compound CCOC(=O)C1=CC=CC=C1N(C)C ORBFAMHUKZLWSD-UHFFFAOYSA-N 0.000 description 3
- 229910001385 heavy metal Inorganic materials 0.000 description 3
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 3
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 3
- 239000007800 oxidant agent Substances 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 229940059574 pentaerithrityl Drugs 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
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- 238000007142 ring opening reaction Methods 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- 238000012719 thermal polymerization Methods 0.000 description 3
- RXYPXQSKLGGKOL-UHFFFAOYSA-N 1,4-dimethylpiperazine Chemical compound CN1CCN(C)CC1 RXYPXQSKLGGKOL-UHFFFAOYSA-N 0.000 description 2
- ZUZAETTVAMCNTO-UHFFFAOYSA-N 2,3-dibutylbenzene-1,4-diol Chemical compound CCCCC1=C(O)C=CC(O)=C1CCCC ZUZAETTVAMCNTO-UHFFFAOYSA-N 0.000 description 2
- BDPNJTJORLNNJR-UHFFFAOYSA-N 2-hydroxy-3-phenoxyprop-2-enoic acid Chemical compound OC(=O)C(O)=COC1=CC=CC=C1 BDPNJTJORLNNJR-UHFFFAOYSA-N 0.000 description 2
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 2
- CIWBSHSKHKDKBQ-JLAZNSOCSA-N Ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(O)=C1O CIWBSHSKHKDKBQ-JLAZNSOCSA-N 0.000 description 2
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
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- DJCNABBQEYPNEQ-UHFFFAOYSA-M (1-hexadecylpyridin-1-ium-2-yl) prop-2-enoate chloride Chemical compound [Cl-].C(C=C)(=O)OC1=[N+](C=CC=C1)CCCCCCCCCCCCCCCC DJCNABBQEYPNEQ-UHFFFAOYSA-M 0.000 description 1
- 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 1
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- FVQMJJQUGGVLEP-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOOC(C)(C)C FVQMJJQUGGVLEP-UHFFFAOYSA-N 0.000 description 1
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 description 1
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- RKHXQBLJXBGEKF-UHFFFAOYSA-M tetrabutylphosphanium;bromide Chemical compound [Br-].CCCC[P+](CCCC)(CCCC)CCCC RKHXQBLJXBGEKF-UHFFFAOYSA-M 0.000 description 1
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Images
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C271/00—Derivatives of carbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C271/06—Esters of carbamic acids
- C07C271/08—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms
- C07C271/24—Esters of carbamic acids having oxygen atoms of carbamate groups bound to acyclic carbon atoms with the nitrogen atom of at least one of the carbamate groups bound to a carbon atom of a ring other than a six-membered aromatic ring
-
- 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
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Description
〔ウレタン(メタ)アクリル化合物〕
本発明にかかる新規なウレタン(メタ)アクリル化合物は、分子内に少なくとも1つの脂環構造もしくは芳香環構造を有するウレタン(メタ)アクリル化合物であり、一般式(1)で表される。このような特定のウレタン(メタ)アクリル化合物は、重合収縮率が小さく、コンポジットレジンなどの歯科修復材料に応用したとき、歯科修復材料の調製時に好適な適度な粘度を有する。また、本発明の歯科材料には、該ウレタン(メタ)アクリル化合物を1種、または2種以上含んで用いることができる。
本発明に係るウレタン(メタ)アクリル化合物の製造方法は特に限定されないが、通常下記スキーム1に示されるジイソシアネート化合物と水酸基含有(メタ)アクリル化合物との付加反応により製造される。
本発明に係る水酸基含有(メタ)アクリル化合物は、工業的に入手可能な化合物も多いが、エポキシ化合物と(メタ)アクリル酸との開環エステル化により得ることもできる。
アセトン、メチルエチルケトンおよびメチルイソブチルケトン等のケトン系溶媒、
酢酸エチルおよび酢酸ブチル等のエステル系溶媒、
ジエチルエーテル、テトラヒドロフランおよびジオキサン等のエーテル系溶媒、
ジクロロメタン、クロロホルム、四塩化炭素、1,2−ジクロロエタンおよびパークレン等のハロゲン系溶媒、
N,N−ジメチルホルムアミド、N,N−ジメチルアセトアミド、N,N−ジメチルイミダゾリジノン、ジメチルスルホキシドおよびスルホランなどの極性溶媒が挙げられる。
これらの溶媒は1種単独で、または2種類以上を併用して用いることができる。
トリエチルアミンおよびトリエタノールアミン等の3級アミン類、
トリメチルアンモニウムクロライドおよびトリエチルベンジルアンモニウムクロライド等の第4級アンモニウム塩類、
テトラブチルホスホニウムブロマイド、テトラフェニルホスホニウムブロマイド等の有機リン塩類および2-メチルイミダゾール等のイミダゾール類、
オクテン酸コバルト等の有機金属化合物類が挙げられる。
本発明に係るジイソシアネート化合物は、工業的に入手可能な化合物も多いく、それらをそのまま使用できるが、たとえば、対応するジアミン化合物とホスゲンとの反応により合成して得ることもできる。
ウレタン(メタ)アクリル化合物は、たとえば、下記の(B)工程を含み、好ましくは、下記の(A)、(B)および(C)を含む工程で製造される。また、得られたウレタン(メタ)アクリル化合物に微量の異物が混入することもあるため、このような異物を濾過により除去する工程を含むことも好ましい。
(B)脱水工程後の水酸基含有(メタ)アクリル化合物、または未脱水の水酸基含有(メタ)アクリル化合物に、ジイソシアネート化合物を滴下により投入して、ウレタン反応を行う工程および
(C)20〜90℃で脱臭を行う工程。
工程(A)は、酸素存在下、水酸基含有(メタ)アクリル化合物に、必要に応じて重合禁止剤やウレタン化触媒などを混合し、20〜90℃の温度にて脱水を行う工程である。工程Aは、水酸基含有(メタ)アクリル化合物中に水分が含まれていると次の工程(B)のウレタン反応時、水分によりジイソシアネート化合物が分解する可能性があるため、行うことが好ましい。
ジブチル錫ジラウレート、ジブチル錫ジオクテートおよびオクタン酸錫などの有機錫化合物、
ナフテン酸銅、ナフテン酸コバルト、ナフテン酸亜鉛、アセチルアセトナトジルコニウム、アセチルアセトナト鉄およびアセチルアセトナトゲルマニウムなどの錫以外のその他の有機金属化合物、
トリエチルアミン、1,4−ジアザビシクロ[2.2.2]オクタン、2,6,7−トリメチル−1−ジアザビシクロ[2.2.2]オクタン、1,8−ジアザビシクロ[5.4.0]ウンデセン、N,N−ジメチルシクロヘキシルアミン、ピリジン、N−メチルモルホリン、N,N,N',N'−テトラメチルエチレンジアミン、N,N,N',N'−テトラメチル−1,3−ブタンジアミン、N,N,N',N'−ペンタメチルジエチレントリアミン、N,N,N',N'−テトラ(3−ジメチルアミノプロピル)−メタンジアミン、N,N'−ジメチルピペラジンおよび1,2−ジメチルイミダゾールなどのアミン化合物およびそれらの塩、
トリ−n−ブチルホスフィン、トリ−n−ヘキシルホスフィン、トリシクロヘキシルホスフィンおよびトリ−n−オクチルホスフィンなどのトリアルキルホスフィン化合物が挙げられる。
工程(B)は、脱水工程後の水酸基含有(メタ)アクリル化合物、または未脱水の水酸基含有(メタ)アクリル化合物に、ジイソシアネート化合物を滴下により投入して、ウレタン反応を行う工程である。
前記工程(B)の終了後、必要に応じて、脱臭を行う工程(C)を有することが好ましい。脱臭することで、良好なウレタン(メタ)アクリル化合物を得ることができる。
本発明の歯科材料には、本発明の目的を損なわない範囲で、必要に応じて、耐熱安定剤、スリップ防止剤、結晶化助剤、核剤、顔料、染料、可塑剤、老化防止剤、酸化防止剤、衝撃改良剤、架橋剤、共架橋剤、架橋助剤、粘着剤、軟化剤、加工助剤等の各種添加剤が配合されていてもよい。
本発明のウレタン(メタ)アクリル化合物を含有する歯科材料を硬化させてなる硬化物は、機械的強度や耐磨耗性、審美性、操作性、安全性に加えて、特に重合硬化時の重合収縮率が小さい。したがって、該硬化物は、歯科材料用に適する。
本発明の歯科材料は、歯科材料組成物の成分として好適に使用できる。
(光)重合開始剤は、歯科分野で用いられる公知の(光)重合開始剤を使用することができ、通常、重合性単量体の重合性と重合条件を考慮して選択される。
t−ブチルパーオキシベンゾエート、ビス−t−ブチルパーオキシイソフタレート、2,5−ジメチル−2,5−ビス(ベンゾイルパーオキシ)ヘキサン、t−ブチルパーオキシ−2−エチルヘキサノエートおよびt−ブチルパーオキシイソプロピルカーボネートなどのパーオキシエステル類、
ジクミルパーオキサイド、ジ−t−ブチルパーオキサイドおよびラウロイルパーオキサイドなどのジアルキルパーオキサイド類、
1,1−ビス(t−ブチルパーオキシ)−3,3,5−トリメチルシクロヘキサンなどのパーオキシケタール類、
メチルエチルケトンパーオキサイドなどのケトンパーオキサイド類、
t−ブチルハイドロパーオキサイドなどのハイドロパーオキサイド類が挙げられる。
2−(ジメチルアミノ)エチルメタクリレート、N,N−ビス〔(メタ)アクリロイルオキシエチル〕−N−メチルアミン、N,N−ジメチルアミノ安息香酸エチル、4−ジメチルアミノ安息香酸ブチル、4−ジメチルアミノ安息香酸ブトキシエチル、N−メチルジエタノールアミン、4−ジメチルアミノベンゾフェノン、N,N−ビス(2−ヒドロキシエチル)−p−トルイジンおよびジメチルアミノフェナントール等の第三級アミン、
シトロネラール、ラウリルアルデヒド、フタルジアルデヒド、ジメチルアミノベンズアルデヒドおよびテレフタルアルデヒド等のアルデヒド類、
2−メルカプトベンゾオキサゾール、デカンチオール、3−メルカプトプロピルトリメトキシシラン、4−メルカプトアセトフェノン、チオサリチル酸およびチオ安息香酸等のチオール基を有する化合物等を挙げることができる。
フィラーは、歯科分野で用いられる公知のフィラーを使用することができ、通常、有機フィラーと無機フィラーに大別される。
重合性単量体は、本発明に係るウレタン(メタ)アクリル化合物以外であって、歯科分野で通常用いられる単量体であれば特に限定されないが、たとえば、α−シアノアクリル酸、(メタ)アクリル酸、α−ハロゲン化アクリル酸、クロトン酸、桂皮酸、ソルビン酸、マレイン酸およびイタコン酸等のエステル化物、(メタ)アクリルアミド、(メタ)アクリルアミド誘導体、ビニルエステル類、ビニルエーテル類、モノ−N−ビニル誘導体およびスチレン誘導体等が挙げられる。中でも、(メタ)アクリレートが好適に用いられる。かかる重合性単量体の例を以下に示す。なお、本発明において、1つのオレフィン性二重結合を有する単量体を一官能性単量体とする。同様に、オレフィン性二重結合が2つのものは二官能性単量体と、3つのものは三官能性単量体とする。
本発明の歯科材料組成物には、本発明の目的を損なわない範囲で、必要に応じて、重合禁止剤、紫外線吸収剤、蛍光剤、顔料等の添加剤を含有していてもよい。
攪拌羽根、温度計および還流管を備えた300ミリリットル4ツ口フラスコ内に3−フェノキシ−2−ヒドロキシアクリレート111.1g(0.5モル)とジブチル錫ジラウレート0.11g(水酸基含有(メタ)アクリル化合物の重量に対し1000ppm)を添加し、60℃に昇温した。続いて、ビスイソシアナトシクロヘキシルメタン(水添MDI)65.6g(0.25モル)を0.5時間かけて滴下したところ、反応温度は80℃に上昇した。全量滴下後反応温度を80〜90℃に保って10時間反応を行った。反応生成物中の水添MDIの重量%を測定したところ0.00重量%であった。
製造例1に記載の3−フェノキシ−2−ヒドロキシアクリレートおよび水添MDIの代わりに表11に示す水酸基含有(メタ)アクリル化合物とジイソシアネートを用いて、製造例1と同様の合成操作を行うことで各種ウレタン(メタ)アクリル化合物を含む歯科材料を得た。
攪拌羽根、温度計および還流管を備えた300ミリリットル4ツ口フラスコ内にアクリル酸14.4g(0.2モル)および触媒としてテトラブチルアンモニウムブロミド0.5g(1.7ミリモル)を添加し、60℃に昇温した。続いて、4−ノニルフェニルグリシジルエーテル55.3g(0.2モル)を0.7時間かけて滴下したところ、反応温度は65℃に上昇した。全量滴下後反応温度を90〜100℃に保って12時間反応を行った。反応終了後、反応液を室温まで冷却し、トルエン200ミリリットルを加えた。得られたトルエン溶液を500ミリリットルの分液ロートに移し、蒸留水を用いて水層のpHは中性になるまで水洗した。水洗後、トルエン層からエバポレーターを用いてトルエンを留去し、2−ヒドロキシ−4−(4-ノニルフェノキシ)プロピルアクリレート60.6g(収率87%)を得た。
製造例15に記載の4-ノニルフェニルグリシジルエーテルとアクリル酸の代わりに表12に示すエポキシ化合物とアクリル酸もしくはメタクリル酸を用いて水酸基含有(メタ)アクリル化合物を製造し、さらにHMDIの代わりに表12に示すジイソシアネートを用いて、製造例15と同様の合成操作を行うことで各種ウレタン(メタ)アクリル化合物を含む歯科材料を得た。
攪拌羽根、温度計および還流管を備えた300ミリリットルの4ツ口フラスコ内にアクリル酸14.4g(0.2モル)および触媒としてテトラブチルアンモニウムブロミド0.5g(1.7ミリモル)を添加し、60℃に昇温した。続いて、4−ノニルフェニルグリシジルエーテル55.3g(0.2モル)を0.7時間かけて滴下したところ、反応温度は65℃に上昇した。全量滴下後、反応温度を90〜100℃に保って12時間反応を行った。反応終了後、反応液を室温まで冷却し、トルエン200ミリリットルを加えた。得られたトルエン溶液を500ミリリットルの分液ロートに移し、蒸留水を用いて水層のpHが中性になるまで水洗した。水洗後、トルエン層からエバポレーターを用いてトルエンを留去し、2−ヒドロキシ−4−(4-ノニルフェノキシ)プロピルアクリレート60.6g(収率87%)を得た。
製造例26に記載の2−ヒドロキシ−4−(4-ノニルフェノキシ)プロピルアクリレートと1,4−シクロヘキサンジメタノールモノアクリレート、およびIPDIの代わりに、表13に示す2種の水酸基含有(メタ)アクリル化合物とジイソシアネートを用いて、製造例26と同様の合成操作を行うことで各種ウレタン(メタ)アクリル化合物を含む歯科材料を得た。
赤外分光光度計(Biorad社製FTS−6000)を用いて、製造例1〜31で得られたウレタン(メタ)アクリル化合物を含む歯科材料のFT−IR測定を行った。
製造例1〜31で得られたウレタン(メタ)アクリル化合物を含む歯科材料70重量部に、粘度調整のための希釈モノマーとしてトリエチレングリコールジメタクリレート(新中村化学工業(株)社製NKエステル3G)30重量部を混合したモノマー組成物を調製し、更にこのモノマー組成物100重量部に対して、カンファーキノン(和光純薬(株)社製)を0.3重量部、N,N−ジメチルアミノ安息香酸エチル(和光純薬(株)社製)を0.3重量部添加して溶解させ、光硬化型モノマー組成物(歯科材料組成物)を調製した。
次いで、上記と同様の操作により、トリエチレングリコ−ルジメタクリレ−ト単独の重合収縮率を測定した。その結果、その重合収縮率は13.0%であった。
結果を表14〜16に示す。
製造例1〜23、28および29で得られたウレタン(メタ)アクリル化合物を含む歯科材料60重量部に、粘度調整のための希釈モノマーとしてトリエチレングリコールジメタクリレート(NKエステル3G)40重量部を混合したモノマー組成物を調製した。
上記実施例のウレタン(メタ)アクリル化合物を含む歯科材料に代えて、歯科用コンポジットレジンに従来広く使用されているメタクリレートモノマーとしてBis−GMA(新中村化学工業(株)社製D−GMA)またはUDMA(根上工業(株)社製SH500S)60重量部に、トリエチレングリコ−ルジメタクリレ−ト(NKエステル3G)40重量部を混合したモノマー組成物を調製した。
結果を表16に示す。
製造例3、12および16で得られたウレタン(メタ)アクリル化合物を含む歯科材料40重量部に、粘度調整のための希釈モノマーとしてDCP−4EO−A(式(6)中、R=水素原子、m+n=4の化合物)、またはDCP−A(式(6)中、R=水素原子、m+n=0の化合物)60重量部を混合したモノマー組成物を調製し、上記実施例と同様にして、該組成物における30℃の粘度をE型粘度計(TV−22型)にて測定した。
Bis−GMA(D−GMA)40重量部に、DCP−4EO−A60重量部を混合したモノマー組成物を用いた以外は、実施例32〜37と同様な操作で、粘度および重合収縮率を求めた。
実施例1〜31(参考例1、2、実施例3、参考例4〜21、実施例22、参考例23〜31)で得られた光硬化型モノマー組成物40重量部と、γ−メタクリロキシプロピルトリメトキシシラン(信越化学工業(株)社製KBM503)10重量部で表面処理した平均粒径1μmのバリウムガラス(NEC SCHOTTコンポーネンツ(株)社製GM8235)60重量部を混合し、均一な光硬化型ペースト(歯科材料組成物)を得た。
上記実施例のウレタン(メタ)アクリル化合物を含む歯科材料に代えて、メタクリレートモノマーとしてBis−GMA(新中村化学工業(株)社製D−GMA)またはUDMA(根上工業(株)社製SH500S)を使用し、実施例100と同様にして、光硬化型ペーストを調製した。
Claims (10)
- 請求項1に記載の歯科材料、(B)重合開始剤および(C)フィラーを含む歯科材料組成物。
- さらに、(D)重合性単量体を含む請求項2に記載の歯科材料組成物。
- 上記一般式(6)中、Rが水素原子を表し、mおよびnはそれぞれ0〜6の整数で、かつ、m+n=2〜6である、請求項4に記載の歯科材料組成物。
- 請求項1に記載の歯科材料、(B)光重合開始剤および(C)フィラーを含む歯科修復材料。
- さらに、(D)重合性単量体を含む請求項6に記載の歯科修復材料。
- 上記一般式(6)中、Rが水素原子を表し、mおよびnはそれぞれ0〜6の整数で、かつ、m+n=2〜6である、請求項8に記載の歯科修復材料。
- 請求項1に記載の歯科材料を硬化させてなる硬化物。
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WO2020031897A1 (ja) | 2018-08-09 | 2020-02-13 | 三井化学株式会社 | 重合開始剤、硬化性組成物、歯科材料および硬化性組成物の調製用キット |
EP3795597A4 (en) | 2018-08-21 | 2022-02-23 | Mitsui Chemicals, Inc. | (METH)ACRYLATE, MONOMER COMPOSITION FOR DENTAL MATERIAL, MOLDING, COMPOSITION FOR DENTAL MATERIAL, DENTAL MATERIAL AND PROCESS FOR PRODUCTION OF (METH)ACRYLATE |
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JP7429559B2 (ja) * | 2020-02-17 | 2024-02-08 | 三井化学株式会社 | (メタ)アクリレート化合物、モノマー組成物、成形体、歯科材料用組成物、歯科材料及び(メタ)アクリレート化合物の製造方法 |
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JPWO2012157566A1 (ja) | 2014-07-31 |
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EP2710994A1 (en) | 2014-03-26 |
WO2012157566A1 (ja) | 2012-11-22 |
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