JP7455822B2 - 光学的立体造形用樹脂組成物 - Google Patents
光学的立体造形用樹脂組成物 Download PDFInfo
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- JP7455822B2 JP7455822B2 JP2021520841A JP2021520841A JP7455822B2 JP 7455822 B2 JP7455822 B2 JP 7455822B2 JP 2021520841 A JP2021520841 A JP 2021520841A JP 2021520841 A JP2021520841 A JP 2021520841A JP 7455822 B2 JP7455822 B2 JP 7455822B2
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- 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
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/60—Preparations for dentistry comprising organic or organo-metallic additives
- A61K6/62—Photochemical radical initiators
-
- 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
- A61C—DENTISTRY; APPARATUS OR METHODS FOR ORAL OR DENTAL HYGIENE
- A61C13/00—Dental prostheses; Making same
- A61C13/0003—Making bridge-work, inlays, implants or the like
- A61C13/0006—Production methods
- A61C13/0013—Production methods using stereolithographic techniques
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K6/00—Preparations for dentistry
- A61K6/70—Preparations for dentistry comprising inorganic additives
- A61K6/71—Fillers
- A61K6/76—Fillers comprising silicon-containing compounds
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B33—ADDITIVE MANUFACTURING TECHNOLOGY
- B33Y—ADDITIVE MANUFACTURING, i.e. MANUFACTURING OF THREE-DIMENSIONAL [3-D] OBJECTS BY ADDITIVE DEPOSITION, ADDITIVE AGGLOMERATION OR ADDITIVE LAYERING, e.g. BY 3-D PRINTING, STEREOLITHOGRAPHY OR SELECTIVE LASER SINTERING
- B33Y70/00—Materials specially adapted for additive manufacturing
-
- 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
- C08F2/00—Processes of polymerisation
- C08F2/46—Polymerisation initiated by wave energy or particle radiation
- C08F2/48—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light
- C08F2/50—Polymerisation initiated by wave energy or particle radiation by ultraviolet or visible light with sensitising agents
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Description
[1]重合性単量体(A)、光重合開始剤(B)、及び有機過酸化物(C)を含有し、
前記重合性単量体(A)が、粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)及び/又は粘度1000mPa・s以下かつ常圧沸点200℃以上の(メタ)アクリルアミド化合物(A-2)を含有し、
前記光重合開始剤(B)が、(ビス)アシルホスフィンオキシド類、α-ヒドロキシケトン系化合物、α-アミノケトン系化合物、ベンゾインアルキルエーテル化合物、チオキサントン類、ケタール類、α-ジケトン類、及びアントラキノン類から選ばれる少なくとも1種である、光学的立体造形用樹脂組成物。
[2]前記重合性単量体(A)が、さらに、粘度1000mPa・sより大きい多官能性(メタ)アクリル酸エステル化合物(A-3)を含有する、[1]に記載の光学的立体造形用樹脂組成物。
[3]前記多官能性(メタ)アクリル酸エステル化合物(A-3)が、分子内にウレタン結合を含有する、[2]に記載の光学的立体造形用樹脂組成物。
[4]前記多官能性(メタ)アクリル酸エステル化合物(A-3)が、ポリエステル、ポリカーボネート、ポリウレタン、ポリエーテル、ポリ共役ジエン、及び水添ポリ共役ジエンからなる群より選ばれる少なくとも1種の構造を有する、[3]に記載の光学的立体造形用樹脂組成物。
[5]前記有機過酸化物(C)が、ケトンペルオキシド、ヒドロペルオキシド、ジアシルペルオキシド、ジアルキルペルオキシド、ペルオキシケタール、ペルオキシエステル、及びペルオキシジカーボネートから選ばれる少なくとも1種である、[1]~[4]のいずれかに記載の光学的立体造形用樹脂組成物。
[6]前記重合性単量体(A)が、粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)を含有し、前記(メタ)アクリル酸エステル化合物(A-1)が、芳香環を有する単官能性(メタ)アクリル酸エステル化合物及び/又は脂環を有する単官能性(メタ)アクリル酸エステル化合物を含有する、[1]~[5]のいずれかに記載の光学的立体造形用樹脂組成物。
[7]前記(メタ)アクリル酸エステル化合物(A-1)が、脂環を有する単官能性(メタ)アクリル酸エステル化合物を含有する、[6]に記載の光学的立体造形用樹脂組成物。
[8]前記脂環を有する単官能性(メタ)アクリル酸エステル化合物が、多脂環を有する単官能性(メタ)アクリル酸エステル化合物である、[7]に記載の光学的立体造形用樹脂組成物。
[9]さらに、フィラー(D)を含有する、[1]~[8]のいずれかに記載の光学的立体造形用樹脂組成物。
[10]前記フィラー(D)の平均1次粒子径が1.0μm以下である、[9]に記載の光学的立体造形用樹脂組成物。
[11][1]~[10]のいずれかに記載の光学的立体造形用樹脂組成物の硬化物からなる歯科材料。
[12][1]~[10]のいずれかに記載の光学的立体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。
重合性単量体(A)は、粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)及び/又は粘度1000mPa・s以下かつ常圧沸点200℃以上の(メタ)アクリルアミド化合物(A-2)を含有する。
粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)(以下、単に「(メタ)アクリル酸エステル化合物(A-1)」と称することがある)は、本発明の光学的立体造形用樹脂組成物において、臭気を発生させることなく光学的立体造形用樹脂組成物を低粘度化して、優れた成形精度を得るために用いられる。また、(メタ)アクリル酸エステル化合物(A-1)は、光学的立体造形用樹脂組成物の硬化物に、強度及び靭性を付与するために用いられる。なお、常圧沸点270℃以上である場合、本発明の光学的立体造形用樹脂組成物から不快な臭気を感じにくくなる。(メタ)アクリル酸エステル化合物(A-1)の常圧沸点は、280℃以上であることが好ましく、285℃以上であることがより好ましい。(メタ)アクリル酸エステル化合物(A-1)の常圧沸点は、450℃以下であることが好ましく、400℃以下であることがより好ましい。(メタ)アクリル酸エステル化合物(A-1)の粘度は750mPa・s以下が好ましく、500mPa・s以下がより好ましい。(メタ)アクリル酸エステル化合物(A-1)は、1種を単独で用いてもよく、2種以上を併用してもよい。
粘度1000mPa・s以下かつ常圧沸点200℃以上の(メタ)アクリルアミド化合物(A-2)(以下、単に「(メタ)アクリルアミド化合物(A-2)」と称することがある)は、本発明の光学的立体造形用樹脂組成物において、臭気を発生させることなく光学的立体造形用樹脂組成物を低粘度化して、優れた成形精度を得るために用いられる。また、(メタ)アクリルアミド化合物(A-2)は、光学的立体造形用樹脂組成物の硬化物に、強度及び靭性を付与するために用いられる。常圧沸点200℃以上である場合、本発明の光学的立体造形用樹脂組成物から不快な臭気を感じにくくなる。(メタ)アクリルアミド化合物(A-2)の常圧沸点は、220℃以上であることが好ましく、240℃以上であることがより好ましい。また、(メタ)アクリルアミド化合物(A-2)の常圧沸点は、特に限定されないが、400℃以下が好ましく、350℃以下がより好ましい。(メタ)アクリルアミド化合物(A-2)の粘度は750mPa・s以下が好ましく、500mPa・s以下がより好ましい。(メタ)アクリルアミド化合物(A-2)は、1種を単独で用いてもよく、2種以上を併用してもよい。
粘度1000mPa・sより大きい多官能性(メタ)アクリル酸エステル化合物(A-3)(以下、単に「多官能性(メタ)アクリル酸エステル化合物(A-3)」と称することがある)は、本発明の光学的立体造形用樹脂組成物において、光学的立体造形用樹脂組成物の硬化物に、強度及び靭性を付与するために用いられる。
本発明に用いられる光重合開始剤(B)は、成形精度と硬化物の強度、靭性、及び色調に優れる観点から、(ビス)アシルホスフィンオキシド類、α-ヒドロキシケトン系化合物、α-アミノケトン系化合物、ベンゾインアルキルエーテル化合物、チオキサントン類、ケタール類、α-ジケトン類、クマリン類、及びアントラキノン類から選ばれる少なくとも1種であり、(ビス)アシルホスフィンオキシド類、α-ヒドロキシケトン系化合物、α-アミノケトン系化合物、ベンゾインアルキルエーテル化合物、チオキサントン類、ケタール類、α-ジケトン類、及びアントラキノン類から選ばれる少なくとも1種が好ましい。
本発明に用いられる有機過酸化物(C)としては、特に限定されず、公知のものを使用することができる。有機過酸化物(C)としては、臭気を発生させることなく、硬化物の強度、靭性、及び色調に優れる観点から、ケトンペルオキシド、ヒドロペルオキシド、ジアシルペルオキシド、ジアルキルペルオキシド、ペルオキシケタール、ペルオキシエステル、ペルオキシジカーボネート等が挙げられる。これらの中でも、硬化性や保存安定性の観点から、ヒドロペルオキシド、ジアシルペルオキシドが好ましく用いられる。
[粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)]
D2.6E:2,2-ビス(4-メタクリロイルオキシポリエトキシフェニル)プロパン(エトキシ基の平均付加モル数:2.6)(新中村化学工業株式会社製)(25℃粘度950mPa・s、常圧換算沸点300℃以上)
DPM:ジシクロペンタニルメタクリレート(日立化成株式会社製)(25℃粘度10mPa・s、常圧換算沸点285℃)
ACMO:N-アクリロイルモルホリン(KJケミカルズ株式会社製)(25℃粘度12mPa・s、常圧換算沸点255℃)
(A-3)-1 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(新中村化学工業株式会社製)(25℃粘度28000mPa・s)
(1)撹拌機、温度調節器、温度計及び凝縮器を備えた内容積5Lの四つ口フラスコに、イソホロンジイソシアネート250g、及びジラウリル酸ジ-n-ブチルスズ0.15gを添加して、撹拌下に70℃に加熱した。
(2)一方、ポリカーボネートポリオール(株式会社クラレ製「クラレポリオール(登録商標) C-1090」;1,6-ヘキサンジオール/3-メチル-1,5-ペンタンジオール=9/1(質量比)からなるポリオール、重量平均分子量Mw1000)1000gを側管付きの滴下漏斗に添加し、この滴下漏斗の液を、上記(1)のフラスコ中に滴下した。なお、上記(1)のフラスコ中の溶液を撹拌しつつ、フラスコの内温を65~75℃に保持しながら4時間かけて等速で滴下した。さらに、滴下終了後、同温度で2時間撹拌して反応させた。
(3)次いで、別の滴下漏斗に添加した2-ヒドロキシエチルアクリレート150gとヒドロキノンモノメチルエーテル0.4gとを均一に溶解させた液をフラスコの内温を55~65℃に保持しながら2時間かけて等速で滴下した後、フラスコ内の溶液の温度を70~80℃に保持しながら4時間反応させることにより、多官能性(メタ)アクリル酸エステル化合物(A-3)-2を得た。GPC分析による多官能性(メタ)アクリル酸エステル化合物(A-3)-2の重量平均分子量Mwは1700であった。
(1)撹拌機、温度調節器、温度計及び凝縮器を備えた内容積5Lの四つ口フラスコに、イソホロンジイソシアネート250g、及びジラウリル酸ジ-n-ブチルスズ0.15gを添加して、撹拌下に70℃に加熱した。
(2)一方、ポリエステルポリオール(株式会社クラレ製「クラレポリオール(登録商標) P-2050」;セバシン酸と3-メチル-1,5-ペンタンジオールからなる重合体ジオール、重量平均分子量Mw2000)2500gを側管付きの滴下漏斗に添加し、この滴下漏斗の液を、上記(1)のフラスコ中に滴下した。なお、上記(1)のフラスコ中の溶液を撹拌しつつ、フラスコの内温を65~75℃に保持しながら4時間かけて等速で滴下した。さらに、滴下終了後、同温度で2時間撹拌して反応させた。
(3)次いで、別の滴下漏斗に添加した2-ヒドロキシエチルアクリレート150gとヒドロキノンモノメチルエーテル0.4gとを均一に溶解させた液をフラスコの内温を55~65℃に保持しながら2時間かけて等速で滴下した後、フラスコ内の溶液の温度を70~80℃に保持しながら4時間反応させることにより、多官能性(メタ)アクリル酸エステル化合物(A-3)-3を得た。GPC分析による多官能性(メタ)アクリル酸エステル化合物(A-3)-3の重量平均分子量Mwは2600であった。
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
THP:1,1,3,3-テトラメチルブチルヒドロペルオキシド(日油株式会社製)
BPO:ベンゾイルペルオキシド(日油株式会社製)
(D)-1:ジメチルジクロロシラン表面処理コロイドシリカ粉(日本アエロジル株式会社製「R972」平均粒子径:0.016μm)
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 Z 8703:1983)下で混合して、実施例1~8及び比較例1~3に係る光学的立体造形用樹脂組成物としてのペーストを調製した。
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64.0mm、幅10.0mm、厚さ3.3mmの直方体の造形物を製造した。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、成形誤差を算出し、成形精度を評価した(n=1)。この方法により、成形誤差が5.0%以下である場合、成形精度に優れ、クラウン等の歯科用補綴物を造形した場合に、適合性に優れたものとなりやすい。
各実施例及び比較例の表1及び表2に記載の光学的立体造形用樹脂組成物について、光造形機(DWS社製DIGITALWAX(登録商標) 028J-Plus;波長405nm)を用いて、厚さ3.3mm×幅10.0mm×長さ64mmの直方体の造形物を製造した。得られた造形物を、メタノールで洗浄し、未重合の単量体を除去した後、歯科技工用LED重合器(株式会社モリタ東京製作所製αライトV;波長400~420nm)を用いて、5分間光照射した。さらに、歯科用加熱重合器(クラレノリタケデンタル株式会社製KL-400)を用いて110℃で10分間加熱した。得られた硬化物を、JIS T 6501:2012(義歯床用アクリル系レジン)に記載の寸法の、試験片(長さ64.0mm、幅10.0mm、厚さ3.3mm)として用いて、曲げ強さ試験を行って評価した。JIS T 6501:2012に従って、万能試験機(株式会社島津製作所製、オートグラフAG-I 100kN)を用いて、クロスヘッドスピード5mm/minで曲げ試験を実施した(n=5)。各試験片の測定値の平均値を算出し、曲げ強さ及び曲げ弾性率とした。試験片の曲げ弾性率としては、歯科用補綴物のうち、テンポラリークラウン、テンポラリークラウンブリッジ、義歯床、歯科用マウスピース等の用途を考慮して、0.1~5.0GPaの範囲が好ましく、0.5~4.0GPaの範囲がより好ましく、1.0~3.0GPaの範囲がさらに好ましい。曲げ強さとしては、歯科用補綴物のうち、テンポラリークラウン、テンポラリークラウンブリッジ、義歯床、歯科用マウスピース等の用途を考慮して、30MPa以上が好ましく、40MPa以上がより好ましく、50MPa以上がさらに好ましい。破断点変位としては、前記曲げ強さ以上の負荷をかけた際に破断しないことが好ましい。変位が10mm以下で破断した場合を靭性が悪いとし、変位が10mm超15mm未満で破断した場合を靭性が良好とし、変位が15mm以上で破断した場合を靭性が特に良好とした。表1、2において、「15<」は変位が15mm以上であり、15mm変位しても破断しなかったことを意味する。
各実施例及び各比較例に係る光学的立体造形用樹脂組成物について、10人のパネラーのうち、不快な臭気を感じた人が2人未満であったものを「○」、不快な臭気を感じた人が2人以上5人未満であったものを「△」、不快な臭気を感じた人が5人以上であったものを「×」とした(n=1)。不快な臭気を感じなければ特に問題はない。
各実施例及び比較例の光学的立体造形用樹脂組成物について、上記と同様の光造形機を用いて、直径15.0mm×厚さ1.0mmのディスク状の造形物を製造した。得られた造形物を、エタノールで洗浄し、未重合の単量体を除去した後、歯科技工用LED重合器(株式会社モリタ東京製作所製αライトV)で5分さらに二次重合、さらに、加熱重合器(クラレノリタケデンタル株式会社製KL-400)を用いて110℃で10分間加熱して、硬化物を得た。得られた硬化物をシリコンカーバイド紙1000番で研磨し、続いて歯科用ラッピングフィルム(3M社製)で研磨した後、分光測色計(コニカミノルタ株式会社製、CM-3610A、JIS Z 8722:2009、条件cに準拠、D65光源)を用いて、黄色度b*値を測定し、平均値を得た(n=5)。該黄色度が10.0以下である場合、目視で無色と認識されやすく、7.0以下が好ましく、5.0以下がより好ましい。
Claims (12)
- 重合性単量体(A)、光重合開始剤(B)、及び有機過酸化物(C)を含有し、
前記重合性単量体(A)が、粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)及び/又は粘度1000mPa・s以下かつ常圧沸点200℃以上の(メタ)アクリルアミド化合物(A-2)を含有し、
前記光重合開始剤(B)が、(ビス)アシルホスフィンオキシド類、α-ヒドロキシケトン系化合物、α-アミノケトン系化合物、ベンゾインアルキルエーテル化合物、チオキサントン類、ケタール類、α-ジケトン類、及びアントラキノン類から選ばれる少なくとも1種であり、
前記(メタ)アクリル酸エステル化合物(A-1)が、芳香環を有する単官能性(メタ)アクリル酸エステル化合物及び/又は脂環を有する単官能性(メタ)アクリル酸エステル化合物を含有する、光学的立体造形用樹脂組成物。 - 前記重合性単量体(A)が、さらに、粘度1000mPa・sより大きい多官能性(メタ)アクリル酸エステル化合物(A-3)を含有する、請求項1に記載の光学的立体造形用樹脂組成物。
- 前記多官能性(メタ)アクリル酸エステル化合物(A-3)が、分子内にウレタン結合を含有する、請求項2に記載の光学的立体造形用樹脂組成物。
- 前記多官能性(メタ)アクリル酸エステル化合物(A-3)が、ポリエステル、ポリカーボネート、ポリウレタン、ポリエーテル、ポリ共役ジエン、及び水添ポリ共役ジエンからなる群より選ばれる少なくとも1種の構造を有する、請求項3に記載の光学的立体造形用樹脂組成物。
- 前記有機過酸化物(C)が、ケトンペルオキシド、ヒドロペルオキシド、ジアシルペルオキシド、ジアルキルペルオキシド、ペルオキシケタール、ペルオキシエステル、及びペルオキシジカーボネートから選ばれる少なくとも1種である、請求項1~4のいずれか1項に記載の光学的立体造形用樹脂組成物。
- 前記重合性単量体(A)が、粘度1000mPa・s以下かつ常圧沸点270℃以上の(メタ)アクリル酸エステル化合物(A-1)を含有する、請求項1~5に記載の光学的立体造形用樹脂組成物。
- 前記(メタ)アクリル酸エステル化合物(A-1)が、脂環を有する単官能性(メタ)アクリル酸エステル化合物を含有する、請求項1~6のいずれか1項に記載の光学的立体造形用樹脂組成物。
- 前記脂環を有する単官能性(メタ)アクリル酸エステル化合物が、多脂環を有する単官能性(メタ)アクリル酸エステル化合物である、請求項7に記載の光学的立体造形用樹脂組成物。
- さらに、フィラー(D)を含有する、請求項1~8のいずれか1項に記載の光学的立体造形用樹脂組成物。
- 前記フィラー(D)の平均1次粒子径が1.0μm以下である、請求項9に記載の光学的立体造形用樹脂組成物。
- 請求項1~10のいずれか1項に記載の光学的立体造形用樹脂組成物の硬化物からなる歯科材料。
- 請求項1~10のいずれか1項に記載の光学的立体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。
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