JP2020528479A - ウレタン成分及び反応性希釈剤を含む光重合性組成物、物品、並びに方法 - Google Patents
ウレタン成分及び反応性希釈剤を含む光重合性組成物、物品、並びに方法 Download PDFInfo
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Abstract
Description
(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、
(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、
(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、
(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、
を含む。成分(a)〜(d)について、以下で詳細に説明する。
本開示の光重合性組成物は、少なくとも1つのウレタン成分を含む。本明細書で使用されるとき、「ウレタン成分」とは、化合物の主鎖に1つ以上のカルバメート官能基を含む化合物を指す。特定の実施形態では、カルバメート官能基は、式I:
−N(H)−C(O)O− I
からなる。
a)少なくとも2つ又は3つ又は4つの(メタ)アクリレート部分を含む。
b)数平均分子量(Mn):1,000〜5,000g/mol、又は1,000〜2000g/mol。
c)(メタ)アクリレート部分がウレタン部分を介して結合している、C1〜C20直鎖又は分枝鎖アルキル部分を含む。
d)粘度:23℃で0.1〜100Pa・s又は1〜50Pa・s。
本開示の光重合性組成物は、少なくとも1種の反応性希釈剤を含む。本明細書の参照目的のための「反応性希釈剤」は、少なくとも1つのウレタン成分と共反応することができる(例えば、付加重合を受けることができる)、少なくとも1つのフリーラジカル反応性基(例えば、エチレン性不飽和基)を含有する成分である。反応性希釈剤は、少なくとも1つの(例えば、高Mn)ウレタン成分よりも小さい分子量を有し、多くの場合、400グラム/モル未満であり、ウレタン官能性基を含有しない(例えば、任意のウレタン官能性基を含まない)。
本明細書に記載の光重合性組成物は、いくつかの例では1つ以上の添加剤、例えば、光開始剤、阻害剤、安定剤、増感剤、吸収調整剤、フィラー及びそれらの組み合わせからなる群から選択される1種以上の添加剤を更に含む。例えば、光重合性組成物は、1種以上の光開始剤を更に含む。好適な例示的光開始剤は、BASF(Ludwigshafen,Germany)から商品名IRGACURE及びDAROCURで入手可能なものであり、1−ヒドロキシシクロヘキシルフェニルケトン(IRGACURE184)、2,2−ジメトキシ−1,2−ジフェニルエタン−1−オン(IRGACURE651)、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(IRGACURE819)、1−[4−(2−ヒドロキシエトキシ)フェニル]−2−ヒドロキシ−2−メチル−1−プロパン−1−オン(IRGACURE2959)、2−ベンジル−2−ジメチルアミノ−1−(4−モルホリノフェニル)ブタノン(IRGACURE369)、2−メチル−1−[4−(メチルチオ)フェニル]−2−モルホリノプロパン−1−オン(IRGACURE907)、オリゴ[2−ヒドロキシ−2−メチル−1−[4−(1−メチルビニル)フェニル]プロパノン]ESACURE ONE(Lamberti S.p.A.,Gallarate,Italy)、2−ヒドロキシ−2−メチル−1−フェニルプロパン−1−オン(DAROCUR1173)、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(IRGACURE TPO)、及び2,4,6−トリメチルベンゾイルフェニルホスフィネート(IRGACURE TPO−L)を含む。更なる好適な光開始剤には、例えば、ベンジルジメチルケタール、2−メチル−2−ヒドロキシプロピオフェノン、ベンゾインメチルエーテル、ベンゾインイソプロピルエーテル、アニソインメチルエーテル、芳香族塩化スルホニル、光活性オキシム、及びこれらの組み合わせが挙げられるが、これらに限定されない。
第2の態様では、本開示は物品を提供する。物品は、光重合性組成物の反応生成物を含み、光重合性組成物は、光重合性組成物の総重量を基準として、
(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、
(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、
(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、
(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、
を含む。多くの実施形態では、物品の光重合性組成物は、以下に詳細に記載されるように、液槽重合される。
(i)光重合性組成物の総重量を基準として、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含む光重合性組成物を準備することと、
(ii)光重合性組成物を選択的に硬化させて物品を形成することと、
(iii)任意に、ステップ(ii)の後に残存する未重合ウレタン成分及び/又は反応性希釈剤を硬化させることと、
を含む。
上記のとおりに調製した後は、本開示の光重合性組成物を多様な付加製造プロセスに使用して、上記のようなフィルムのキャスティングを含む、様々な物品を作製することができる。3次元物品を作製するための一般化された方法100を図1に示す。方法の各ステップについて、下記に詳細に説明する。まず、ステップ110では、所望の光重合性組成物(例えば、少なくとも1つのウレタン成分、少なくとも1種の反応性希釈剤、及び光開始剤を含む)を準備し、付加製造デバイスによって又は付加製造デバイス内で使用するためのリザーバー、カートリッジ、又は他の好適な容器内に導入する。付加製造デバイスは、ステップ120でコンピュータ化された設計命令のセットに従って、光重合性組成物を選択的に硬化する。ステップ130において、ステップ110及び/又はステップ120を繰り返して多層を形成し、3次元構造を含む物品(例えば、歯列矯正アライナー)を作製する。場合により、ステップ140において、未硬化の光重合性組成物を物品から除去し、更に任意に、ステップ150において、物品を追加の硬化に供して物品内の残りの未硬化の光重合性成分を重合させる。
物品の特に興味深い1つの実装形態の概要を図3に示す。付加製造物品300は透明トレイアライナーであり、患者の歯の一部又は全部にわたって取り外し可能な態様で配置することができる。いくつかの実施形態では、装具300は、複数の段階的調整装具のうちの1つである。装具300は、内部空洞を有するシェルを含んでよい。内部空洞は、歯を受け入れ、1つの歯の配列から連続する歯の配列に弾性的に再配置するように形成される。内部空洞は複数の受け部を含んでよく、その各々は、患者の歯列弓のそれぞれの歯と接続し、受け入れるようになっている。隣接する受け部の付近の領域は互いに連通し得るが、受け部は空洞の長さに沿って互いに離隔される。いくつかの実施形態では、シェルは上顎又は下顎に存在する全ての歯に嵌合する。通常、歯のうちの特定の1つのみが再配置され、他の歯は、その歯又は治療対象の歯に対して弾性的な再配置力を加えながら歯科装具を所定の位置に保持する基部又はアンカーの領域を提供することになる。
実施形態1は、光重合性組成物である。光重合性組成物は、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、を含む。光重合性組成物は、光重合性組成物の総重量を基準として、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を更に含む。
以降の実施例で使用される材料を表1に要約する。
完全な混合を確保するために、成分を一晩回転混合することによって、以下の表2に列挙した調合に従って樹脂を調製した。
40℃にて0.1[1/s]の剪断速度で40mmコーンプレート測定システムを使用するTA Instruments AR−G2磁気ベアリングレオメーターを用いて、実施例の樹脂の絶対的(例えば、動的)粘度を測定した。2つの複製を測定し、平均値を以下の表3の粘度(単位:Pa・s)として報告した。
表1に示す実施例1(E−1)調合物をガラスジャー内で混合した。E−1混合物をローリングミキサー上に置き、均質な混合物を作製した。混合物を脱気し、THINKYプラネタリーミキサー(株式会社シンキー、東京)内で、真空下で2000rpmにて90秒間混合した。次いで、混合物をシリコーンドッグボーン成形型(V型成形型、ASTM D638−10)に注いだ。充填された成形型を2枚のガラス板の間に置き、広域スペクトルUVチャンバ(Dymax Light Curing Systems Model 2000 Flood)内で5分間硬化させた。ASTM D638−10に従い、試料を離型し、チャンバ内で更に5分間硬化させた。これらのドッグボーンを、5kNのロードセルを有するInsight MTS上で5mm/分の速度で試験した。5つの複製試料を試験し、平均及び標準偏差を報告する。ASTM D638−10に従い、試料の引張強度、引張弾性率及び破断伸びを決定し、以下の表4に示した。
385nm及び約23mW/cm2のパワーのLED光源を使用して、Asiga Pico 2プリンタで、E−3及びE−7樹脂の調合物を光重合した。ASTM D638−10に従うV型の引張試験棒を製造した。プリンタの樹脂浴を、光重合の前に35〜40℃に加熱し、引張試験棒を製造することができるように粘度を低下させた。使用した設定は、スライス厚=50μm、バーンイン層=3、分離速度=10mm/秒、層当たりのスライド数=1、バーンイン露光時間=15.0秒、通常露光時間=3.1秒であった。次に試験棒をイソプロパノール中で洗浄して未反応樹脂を除去した。次いで、試験棒を、融合ランプ下で、各側で90分間ずつ後硬化させた。後硬化ドッグボーンを、5kNのロードセルを有するInsight MTS上で5mm/分の速度で試験した。5つの複製試料を試験し、平均及び標準偏差を報告する。試料の引張強度をASTM D638−10に従って決定し、以下の表5に示す。
385nm及び約16mW/cm2のパワーのLED光源を使用して、Asiga Pico 2HDプリンタで、E−3の調合物を光重合した。アライナーのSTLファイルをソフトウェアにロードし、支持構造を生成した。プリンタの樹脂浴を、光重合の前に35〜40℃に加熱し、物品を製造することができるように粘度を低下させた。使用した設定は、スライス厚=50μm、バーンイン層=3、分離速度=10mm/秒、層当たりのスライド数=1、バーンイン露光時間=15.0秒、通常露光時間=3.1秒であった。次に光重合アライナーをイソプロパノール中で洗浄し、未反応樹脂を除去し、次いで各側で90分間ずつ融合ランプの下で後硬化させた。光重合アライナーは、付加製造部品の精度を示すモデルに適合する。アライナーはまた、許容可能な強度及び可撓性を有していた。
Claims (18)
- 光重合性組成物であって、前記光重合性組成物の総重量を基準として、
(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、
(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、
(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、
(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、
を含み、
0.1[1/s]の剪断速度で40mmコーンプレート測定システムを使用する磁気ベアリングレオメーターを用いて決定して、40℃の温度で10Pa・s以下の粘度を有する、
光重合性組成物。 - 少なくとも1種のウレタンオリゴマーが、ウレタン(メタ)アクリレート、ウレタンアクリルアミド、又はこれらの組み合わせを含み、前記少なくとも1つのウレタン成分が、アルキル、ポリアルキレン、ポリアルキレンオキシド、アリール、ポリカーボネート、ポリエステル、ポリアミド、及びこれらの組み合わせから選択される連結基を含む、請求項1に記載の光重合性組成物。
- 前記少なくとも1種のウレタンが、高Mnウレタン成分と低Mnウレタン成分とを含み、前記高Mnウレタン成分と前記低Mnウレタン成分との比が、高Mnウレタン成分対低Mnウレタン成分95:5〜高Mnウレタン成分対低Mnウレタン成分80:20の範囲である、請求項1又は2に記載の光重合性組成物。
- 前記少なくとも1種の反応性希釈剤が、200グラム/モル〜400グラム/モル(両端の値を含む)の分子量を含む、請求項1〜3のいずれか一項に記載の光重合性組成物。
- 前記少なくとも1種の反応性希釈剤が、(メタ)アクリレート、ポリアルキレンオキシドジ(メタ)アクリレート、アルカンジオールジ(メタ)アクリレート、又はこれらの組み合わせを含む、請求項1〜4のいずれか一項に記載の光重合性組成物。
- 単官能性成分を含まない、請求項1〜5のいずれか一項に記載の光重合性組成物。
- 光重合性組成物の反応生成物を含む物品であって、前記光重合性組成物が、前記光重合性組成物の総重量を基準として、
(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、
(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、
(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、
(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、
を含み、前記物品が25%以上の破断伸びを呈する、
物品。 - 歯列矯正物品を含む、請求項7に記載の物品。
- 1つ以上のチャネル、1つ以上のアンダーカット、1つ以上の穿孔、又はこれらの組み合わせを含む、請求項7又は8に記載の物品。
- 30%以上の破断伸びを含む、請求項7〜9のいずれか一項に記載の物品。
- ASTM D638−10に従って決定して、20メガパスカル(MPa)以上の引張強度を含む、請求項7〜10のいずれか一項に記載の物品。
- ASTM D638−10に従って決定して、200MPa以上の弾性率を含む、請求項7〜11のいずれか一項に記載の物品。
- 物品の製造方法であって、
(i)光重合性組成物の総重量を基準として、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含む光重合性組成物を準備することと、
(ii)前記光重合性組成物を選択的に硬化させて物品を形成することと、
(iii)任意に、ステップ(ii)の後に残存する未重合ウレタン成分及び/又は反応性希釈剤を硬化させることと、
を含み、前記物品が25%以上の破断伸びを呈する、
方法。 - (iv)ステップ(i)及び(ii)を繰り返して多層を形成し、ステップ(iii)の前に3次元構造を含む物品を作製することを更に含む、請求項13に記載の方法。
- 物品の3次元モデルを表すデータを有し、3Dプリンタとインタフェースする1つ以上のプロセッサによってアクセスされたときに3Dプリンタに物品を作製させる、非一時的機械可読媒体であって、
前記物品が、光重合性組成物の反応生成物を含み、前記光重合組成物が、前記光重合性組成物の総重量を基準として、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含み、前記物品が25%以上の破断伸びを呈する、
非一時的機械可読媒体。 - 非一時的機械可読媒体から、物品の3Dモデルを表すデータを取り出すことであって、前記物品が、光重合性組成物の反応生成物を含み、前記光重合性組成物が、前記光重合性組成物の総重量を基準として、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含む、取り出すことと、
1つ以上のプロセッサによって、前記データを使用して製造デバイスとインタフェースする3Dプリンティングアプリケーションを実行することと、
前記製造デバイスによって、前記物品の物理的オブジェクトを生成することと、を含み、前記物品が25%以上の破断伸びを呈する、
方法。 - 1つ以上のプロセッサを有する製造デバイスによって、物品の複数の層を規定するデータを含むデジタルオブジェクトを受信することであって、
前記物品が、光重合性組成物の反応生成物を含み、前記光重合組成物が、前記光重合性組成物の総重量を基準として、(a)50重量%〜90重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含む、受信することと、
付加製造プロセスによる前記製造デバイスを用いて、前記デジタルオブジェクトに基づく前記物品を生成することであって、前記物品が25%以上の破断伸びを呈する、生成することと、を含む方法。 - 物品の3Dモデルを表示するディスプレイと、
ユーザーによって選択された3Dモデルに応じて、物品の物理的オブジェクトを3Dプリンタに作製させる、1つ以上のプロセッサと、
を含むシステムであって、
前記物品が、光重合性組成物の反応生成物を含み、前記光重合組成物が、前記光重合性組成物の総重量を基準として、(a)50重量%〜80重量%(両端の値を含む)の少なくとも1つのウレタン成分と、(b)5重量%〜50重量%(両端の値を含む)の少なくとも1種の反応性希釈剤と、(c)0.1重量%〜5重量%(両端の値を含む)の光開始剤と、(d)存在する場合は0.001重量%〜1重量%(両端の値を含む)の量の、任意の阻害剤と、を含み、前記物品が25%以上の破断伸びを呈する、
システム。
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CN110997744A (zh) | 2020-04-10 |
JP2023159151A (ja) | 2023-10-31 |
US20200140614A1 (en) | 2020-05-07 |
BR112020001626A2 (pt) | 2020-07-21 |
KR20200035264A (ko) | 2020-04-02 |
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