JP2022041276A - 光造形用樹脂組成物 - Google Patents
光造形用樹脂組成物 Download PDFInfo
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- JP2022041276A JP2022041276A JP2020146381A JP2020146381A JP2022041276A JP 2022041276 A JP2022041276 A JP 2022041276A JP 2020146381 A JP2020146381 A JP 2020146381A JP 2020146381 A JP2020146381 A JP 2020146381A JP 2022041276 A JP2022041276 A JP 2022041276A
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- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 3
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- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- GUCYFKSBFREPBC-UHFFFAOYSA-N [phenyl-(2,4,6-trimethylbenzoyl)phosphoryl]-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)P(=O)(C=1C=CC=CC=1)C(=O)C1=C(C)C=C(C)C=C1C GUCYFKSBFREPBC-UHFFFAOYSA-N 0.000 description 3
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- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- KIQKWYUGPPFMBV-UHFFFAOYSA-N diisocyanatomethane Chemical compound O=C=NCN=C=O KIQKWYUGPPFMBV-UHFFFAOYSA-N 0.000 description 3
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 230000003993 interaction Effects 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
- 238000010030 laminating Methods 0.000 description 3
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
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- 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
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- TXBCBTDQIULDIA-UHFFFAOYSA-N 2-[[3-hydroxy-2,2-bis(hydroxymethyl)propoxy]methyl]-2-(hydroxymethyl)propane-1,3-diol Chemical compound OCC(CO)(CO)COCC(CO)(CO)CO TXBCBTDQIULDIA-UHFFFAOYSA-N 0.000 description 2
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- CADOLDOQCJTEBR-UHFFFAOYSA-N 11-trimethoxysilylundecyl prop-2-enoate Chemical compound CO[Si](OC)(OC)CCCCCCCCCCCOC(=O)C=C CADOLDOQCJTEBR-UHFFFAOYSA-N 0.000 description 1
- IVBBKDXIZQKTOK-UHFFFAOYSA-N 16-phosphonooxyhexadecyl prop-2-enoate Chemical compound OP(O)(=O)OCCCCCCCCCCCCCCCCOC(=O)C=C IVBBKDXIZQKTOK-UHFFFAOYSA-N 0.000 description 1
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- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
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- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- PXZQEOJJUGGUIB-UHFFFAOYSA-N isoindolin-1-one Chemical compound C1=CC=C2C(=O)NCC2=C1 PXZQEOJJUGGUIB-UHFFFAOYSA-N 0.000 description 1
- 239000006233 lamp black Substances 0.000 description 1
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- 239000005055 methyl trichlorosilane Substances 0.000 description 1
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- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
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- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000013001 point bending Methods 0.000 description 1
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- 239000004417 polycarbonate Substances 0.000 description 1
- 125000003367 polycyclic group Chemical group 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
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- 239000004814 polyurethane Substances 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
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- 229910010271 silicon carbide Inorganic materials 0.000 description 1
- 150000003377 silicon compounds Chemical class 0.000 description 1
- GCLGEJMYGQKIIW-UHFFFAOYSA-H sodium hexametaphosphate Chemical compound [Na]OP1(=O)OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])OP(=O)(O[Na])O1 GCLGEJMYGQKIIW-UHFFFAOYSA-H 0.000 description 1
- 235000019982 sodium hexametaphosphate Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 229940075582 sorbic acid Drugs 0.000 description 1
- 235000010199 sorbic acid Nutrition 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 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
- 150000003440 styrenes Chemical class 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000001577 tetrasodium phosphonato phosphate Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- JOUDBUYBGJYFFP-FOCLMDBBSA-N thioindigo Chemical compound S\1C2=CC=CC=C2C(=O)C/1=C1/C(=O)C2=CC=CC=C2S1 JOUDBUYBGJYFFP-FOCLMDBBSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
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- GQIUQDDJKHLHTB-UHFFFAOYSA-N trichloro(ethenyl)silane Chemical compound Cl[Si](Cl)(Cl)C=C GQIUQDDJKHLHTB-UHFFFAOYSA-N 0.000 description 1
- ORVMIVQULIKXCP-UHFFFAOYSA-N trichloro(phenyl)silane Chemical compound Cl[Si](Cl)(Cl)C1=CC=CC=C1 ORVMIVQULIKXCP-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
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- JLGNHOJUQFHYEZ-UHFFFAOYSA-N trimethoxy(3,3,3-trifluoropropyl)silane Chemical compound CO[Si](OC)(OC)CCC(F)(F)F JLGNHOJUQFHYEZ-UHFFFAOYSA-N 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-UHFFFAOYSA-N 0.000 description 1
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- 239000011882 ultra-fine particle Substances 0.000 description 1
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Abstract
Description
[1]重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)、(メタ)アクリルアミド化合物(b)、光重合開始剤(c)、及び平均粒子径が0.75~10μmである球状無機粒子(d)を含有し、
前記球状無機粒子(d)の含有量が、前記重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)、(メタ)アクリルアミド化合物(b)、及びその他の重合性単量体の合計量100質量部に対して50~400質量部である、光造形用樹脂組成物;
[2]前記球状無機粒子(d)の真球度が0.70~0.99である、[1]に記載の光造形用樹脂組成物;
[3]前記光造形用樹脂組成物の造形物の曲げ強度が120MPa以上、かつ曲げ弾性率が5.0GPa以上である、[1]又は[2]に記載の光造形用樹脂組成物;
[4]前記重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)の重量平均分子量が500以下である、[1]~[3]のいずれかに記載の光造形用樹脂組成物;
[5]前記(メタ)アクリルアミド化合物(b)が単官能(メタ)アクリルアミド化合物である、[1]~[4]のいずれかに記載の光造形用樹脂組成物;
[6]前記単官能(メタ)アクリルアミド化合物がN-アクリロイルモルホリンである、[5]に記載の光造形用樹脂組成物;
[7][1]~[6]のいずれかに記載の光造形用樹脂組成物の硬化物からなる歯科材料;
[8][1]~[6]のいずれかに記載の光造形用樹脂組成物の硬化物からなる歯科用補綴物;
[9][1]~[6]のいずれかに記載の光造形用樹脂組成物を用いて、光学的立体造形法によって立体造形物を製造する方法;
[10]前記光学的立体造形法が、吊り上げ式液槽光造形法である、[9]に記載の製造方法。
重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)(以下、単に「ウレタン化(メタ)アクリル化合物(a)」ともいう。)は、本発明の光造形用樹脂組成物において、光造形用樹脂組成物の造形物の強度、弾性、成形精度及び耐摩耗性を高めるために用いられる。重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)は、ポリマー構造を含有しないウレタン化(メタ)アクリル化合物、ポリマー構造を含有するウレタン化(メタ)アクリル化合物が挙げられる。
(メタ)アクリルアミド化合物(b)は、本発明の光造形用樹脂組成物において、光造形用樹脂組成物の粘度を低減するため、並びに硬化性及び耐摩耗性を付与するために用いられる。さらに、本発明では高強度、高弾性を目的として比較的大きい無機粒子が配合されるが、一般的に粒子径が大きく、かつ球状のフィラーを配合した場合、フィラーが脱落しやすい傾向となり、耐摩耗性が低下する。しかしながら、(メタ)アクリルアミド(b)はウレタン化(メタ)アクリル化合物(a)と共重合することによって、強固かつフィラーとの相互作用が強い硬化物を与えるため、フィラーの脱落を抑制しながら、高強度化、高弾性化されることから、耐摩耗性に優れた硬化物が得られるものと推測される。
本発明に用いられる光重合開始剤(c)は、一般工業界で使用されている光重合開始剤から選択して使用でき、中でも歯科用途に用いられている光重合開始剤が好ましく用いられる。
球状無機粒子(d)は、本発明の光造形用樹脂組成物において、特定の含有量の場合に、造形性を損なうことなく高弾性化するために用いられる。すなわち、球状無機粒子(d)が、球状であることによって、光造形用樹脂組成物に剪断応力が掛けられたときに、粒子同士の摩擦抵抗或いは相互作用が小さくなり、光造形用樹脂組成物が低粘度化されるため、造形性に優れる。また、特定の粒径とすることによって、粘度の上昇を抑えつつ、緻密に充填されるため、無機粒子の剛性が造形物に発現し、高弾性化する。しかしながら、無機粒子の粒径が小さすぎる場合、粒子同士の相互作用が大きくなり、高粘度化するだけでなく、無機粒子の剛性が発現しにくい。一方、無機粒子の粒径が大きすぎる場合、組成物が緻密に充填されにくくなり不均一化するため、高弾性化しにくくなる。また、球状無機粒子(d)は、光造形用樹脂組成物の硬化物に耐摩耗性を付与する。
円形度=(4・π・S)/(L2)
(式中、Sは画像処理で得られた粒子の面積を表し、Lは粒子の周囲長を表す。)
また、円形度の算出に用いる粒子径としては、円相当径(真円と仮定した場合の直径)=(4・S/π)1/2とした。
UDMA:2,2,4-トリメチルヘキサメチレンビス(2-カルバモイルオキシエチル)ジメタクリレート(共栄社化学株式会社製 分子量:471)
U4TH:N,N’-(2,2,4-トリメチルヘキサメチレン)ビス[2-(アミノカルボキシ)プロパン-1,3-ジオール]テトラメタクリレート(共栄社化学株式会社製 分子量:673)
ACMO:N-アクリロイルモルホリン(KJケミカルズ株式会社製)
DEAA:N,N-ジエチルアクリルアミド(KJケミカルズ株式会社製)
TPO:2,4,6-トリメチルベンゾイルジフェニルホスフィンオキシド
BAPO:ビス(2,4,6-トリメチルベンゾイル)フェニルホスフィンオキシド
球状無機粒子(d)-1:γ-メタクリロイルオキシプロピルトリメトキシシラン処理シリカ(商品名「アドマファイン(登録商標)SO-C4」、株式会社アドマテックス製、平均粒子径:1.0μm、真球度:0.96)
球状無機粒子(d)-2:γ-メタクリロイルオキシプロピルトリメトキシシラン処理シリカ(商品名「アドマファイン(登録商標)SO-C6」、株式会社アドマテックス製、平均粒子径:2.0μm、真球度:0.97)
Bis-GMA:2,2-ビス〔4-(3-メタクリロイルオキシ-2-ヒドロキシプロポキシ)フェニル〕プロパン(新中村化学工業株式会社製)
TEGDMA:トリエチレングリコールジメタクリレート(新中村化学工業株式会社製)
BHT:3,5-ジ-t-ブチル-4-ヒドロキシトルエン
表1及び表2に示す分量で各成分を常温(20℃±15℃、JIS(日本工業規格) Z 8703:1983)下で混合して、実施例1~7及び比較例1~5に係る光造形用樹脂組成物としてのインクを調製した。
1.造形の可否
各実施例及び比較例のインクについて、光造形機(DWS社製 DIGITALWAX(登録商標) 020D)を用いて、1辺の長さが10.000mmの立方体の立体造形物を、造形ピッチ50μm、レーザー走査速度4300mm/secで製造した。光造形機は、コート材で表面処理されたトレイ及び台座を備える。造形中の立体造形物の光造形機が備える台座からの脱落、造形途切れ、容器の破壊(樹脂組成物を充填しているトレイのコート材の損傷)等がなく、造形可能か目視により観察した(n=5)。1つでも造形できないものがあれば、「造形不可」とした。
2.流動性
一辺の長さが50mmの正方形の底面を有し、厚さ0.05mmのPETフィルムを平面に置き、その中心に各実施例及び比較例のインクを0.5ml滴下して、25℃の恒温室内にて、10分間静置した。次いで、円形に広がったインクの最大径(長径)と最小径(短径)の平均を取り、インクの径を算出した。各実施例及び比較例のインクについて、3つのサンプルをこの方法で測定し、インクの径を算出した(n=3)。算出値の平均値を表1及び表2に示す。さらに、この3回の測定結果の平均値を流動性の測定値とした。流動性が大きいほどインクが流れやすく、造形性に優れることを示す。この試験での粘度が30mm以上のものは、流動性が高く造形性に優れ、40mm以上のものがより好ましい。
3.成形精度
各実施例及び比較例のインクについて、光造形機(DWS社製 DIGITALWAX(登録商標) 020D)を用いて、1辺の長さが10.000mmの立方体の立体造形物を、造形ピッチ50μm、レーザー走査速度4300mm/secで製造した。得られた立体造形物を、エタノールで洗浄し、未重合の重合性単量体を除去した後、マイクロメーターを用いて寸法(単位:mm)を測定し、下記の式により、成形精度について成形誤差を算出した(n=5)。測定値の平均値を表1及び表2に示す。該成形誤差が1.0%以下である場合、成形精度に優れ、歯科用途においてクラウン或いはブリッジを造形した場合に、適合性に優れたものとなりやすく、0.80%以下が好ましい。
各実施例及び比較例の表1及び表2に記載の組成物について、光造形機(DWS社製 DIGITALWAX(登録商標) 028J-Plus)を用いて、長さ25.0mm×幅2.0mm×厚さ2.0mmの直方体の造形物を、造形ピッチ50μm、レーザー走査速度4300mm/secで製造した。得られた造形物を、メタノールで洗浄し、未重合の重合性単量体を除去した後、光照射機(EnvisionTEC社製 Otoflash(登録商標)G171)を用いて追い込み重合し、硬化物を得た。得られた硬化物をシリコンカーバイド紙300番で研磨した後、精密万能試験機(株式会社島津製作所製、商品名「AG-I 100N」)を用いて、支点間距離20mm、クロスヘッドスピード1mm/分で曲げ強さ(3点曲げ強さ)及び曲げ弾性率を測定した(n=5)。測定値の平均値を表1及び表2に示す。曲げ強さが120MPa以上であり、かつ曲げ弾性率が5.0GPa以上である硬化物は機械的強度に優れ、曲げ強さが140MPa以上であり、かつ曲げ弾性率が6.0GPa以上である硬化物は機械的強度により優れる。
各実施例及び比較例の表1及び表2に記載の組成物について、光造形機(DWS社製 DIGITALWAX(登録商標) 028J-Plus)を用いて、縦11cm×横11cm×厚さ0.5cmのシートの造形物を、造形ピッチ50μm、レーザー走査速度4300mm/secで製造した。得られた造形物を、メタノールで洗浄し、未重合の重合性単量体を除去した後、光照射機(EnvisionTEC社製 Otoflash(登録商標)G171)を用いて追い込み重合し、硬化物を得た。該シートから直径10.5cmの円形状に試験片を切り取り、JIS K 6264-2:2005(ランボーン摩耗試験)に準じて、研磨輪としてH-22摩耗輪(TABER INDUSTRIES社製)を用い、1kg荷重、1000回転の条件下でテーバー摩耗量を測定した(n=2)。測定値の平均値を表1及び表2に示す。この試験で摩耗量が55mm3以下であれば耐摩耗性が優れ、50mm3以下であれば耐摩耗性がより優れる。
無機粒子2:石英(MARUWA QUARTZ製)をボールミルで粉砕し、平均粒子径が約2.8μmの石英粉を得た後、この石英粉100質量部に対して、通法により3質量部の3-メタクリロイルオキシプロピルトリメトキシシランで表面処理を行った破砕状無機粒子。
ウレタンアクリレート1:ポリエーテル系ウレタンジアクリレート(新中村化学工業株式会社製 分子量1400)
Claims (10)
- 重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)、(メタ)アクリルアミド化合物(b)、光重合開始剤(c)、及び平均粒子径が0.75~10μmである球状無機粒子(d)を含有し、
前記球状無機粒子(d)の含有量が、前記重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)、(メタ)アクリルアミド化合物(b)、及びその他の重合性単量体の合計量100質量部に対して50~400質量部である、光造形用樹脂組成物。 - 前記球状無機粒子(d)の真球度が0.70~0.99である、請求項1に記載の光造形用樹脂組成物。
- 前記光造形用樹脂組成物の造形物の曲げ強度が120MPa以上、かつ曲げ弾性率が5.0GPa以上である、請求項1又は2に記載の光造形用樹脂組成物。
- 前記重量平均分子量が1000以下のウレタン化(メタ)アクリル化合物(a)の重量平均分子量が500以下である、請求項1~3のいずれか1項に記載の光造形用樹脂組成物。
- 前記(メタ)アクリルアミド化合物(b)が単官能(メタ)アクリルアミド化合物である、請求項1~4のいずれか1項に記載の光造形用樹脂組成物。
- 前記単官能(メタ)アクリルアミド化合物がN-アクリロイルモルホリンである、請求項5に記載の光造形用樹脂組成物。
- 請求項1~6のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる歯科材料。
- 請求項1~6のいずれか1項に記載の光造形用樹脂組成物の硬化物からなる歯科用補綴物。
- 請求項1~6のいずれか1項に記載の光造形用樹脂組成物を用いて、光学的立体造形法によって立体造形物を製造する方法。
- 前記光学的立体造形法が、吊り上げ式液槽光造形法である、請求項9に記載の製造方法。
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