JP7216644B2 - 前駆体から物体を製造する方法、および付加製造法におけるラジカル架橋性樹脂の使用 - Google Patents
前駆体から物体を製造する方法、および付加製造法におけるラジカル架橋性樹脂の使用 Download PDFInfo
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- JP7216644B2 JP7216644B2 JP2019524441A JP2019524441A JP7216644B2 JP 7216644 B2 JP7216644 B2 JP 7216644B2 JP 2019524441 A JP2019524441 A JP 2019524441A JP 2019524441 A JP2019524441 A JP 2019524441A JP 7216644 B2 JP7216644 B2 JP 7216644B2
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Description
I)フリーラジカル架橋樹脂を担体の上に堆積させて、前駆体の第1の選択断面に対応する、前記担体に接合された構成材料の層を得る工程、
II)前記構成材料の先に施工された層の上にフリーラジカル架橋樹脂を堆積させて、前記前駆体のさらなる選択断面に対応する、先に施工された層に接合された前記構成材料のさらなる層を得る工程、
III)前記前駆体が形成されるまで工程II)を繰り返す工程、
を含み、
少なくとも工程II)におけるフリーラジカル架橋樹脂の堆積が、前記前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の選択された領域の露光および/または照射によって行われ、前記フリーラジカル架橋性樹脂が、5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有する方法に関する。
I)フリーラジカル架橋樹脂を担体の上に堆積させて、前駆体の第1の選択断面に対応する、前記担体に接合された構成材料の層を得る工程、
II)前記構成材料の先に施工された層の上にフリーラジカル架橋樹脂を堆積させて、前記前駆体のさらなる選択断面に対応する、先に施工された層に接合された前記構成材料のさらなる層を得る工程、
III)前記前駆体が形成されるまで工程II)を繰り返す工程、
を含み、
少なくとも工程II)におけるフリーラジカル架橋樹脂の堆積が、前記前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の選択された領域の露光および/または照射によって行われ、前記フリーラジカル架橋性樹脂が、5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有する。
IV)工程III)の後に得られた前駆体を、得られた前駆体のフリーラジカル架橋樹脂中に存在するNCO基を少なくとも部分的にイソシアヌレート基に三量化するのに十分な条件下で処理して、物体を得る工程、
がさらに実施される。
前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比は、1:5以上5:1以下(好ましくは1:4以上4:1以下、より好ましくは1:3以上3:1以下)の範囲内であり、
前記硬化性化合物において、NCO基対イソシアヌレート基のモル比は、100:1以下1:2以上(好ましくは70:1以下1:1以上、より好ましくは50:1以下2:1以上)の範囲内であり、ならびに
前記硬化性成分において、オレフィン性C=C二重結合対イソシアヌレート基のモル比は100:1以下1:5以上(好ましくは70:1以下1:3以上、より好ましくは50:1以下2:1以上)の範囲内である。
および/または
イソシアヌレート三量化触媒は、酢酸カリウム、クラウンエーテルと組み合わせた酢酸カリウム、ポリエチレングリコールと組み合わせた酢酸カリウム、ポリプロピレングリコールと組み合わせた酢酸カリウム、オクタン酸スズ、ナトリウムフェノキシド、水酸化カリウム、トリオクチルホスフィン、および/またはトリブチルスズオキシドから選択される。
-担体は容器の内側に配置されており、重力の方向に垂直に下降可能である、
-容器は、少なくとも担体および担体の上に堆積した架橋樹脂を覆うのに十分な量のフリーラジカル架橋性樹脂を含む、
-各工程II)の前に、垂直方向に見て構成材料の最上層の上にフリーラジカル架橋性樹脂の層が形成されるように、担体を所定の距離だけ降下させる、
-工程II)において、エネルギービームが、前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の層の選択された領域を露光および/または照射する。
-担体は容器の内側に配置されており、重力の方向とは反対に垂直に上昇可能である、
-容器はフリーラジカル架橋性樹脂を提供する、
-各工程II)の前に、垂直方向に見て構成材料の最下層の下にフリーラジカル架橋性樹脂の層が形成されるように担体を所定の距離だけ上昇させる、
-工程II)において、複数のエネルギービームが、前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の層の選択された領域を同時に露光および/または照射する。
-工程II)において、フリーラジカル架橋性樹脂が前駆体の個々の選択断面に対応する印刷ヘッドから塗布され、その後露光および/または照射される。
ここで、NCO基対オレフィン性C=C二重結合のモル比は、1:5以上5:1以下(好ましくは1:4以上4:1以下、より好ましくは1:3以上3:1以下)の範囲内であり、
NCO基対イソシアヌレート基のモル比は、100:1以下1:2以上(好ましくは70:1以下1:1以上、より好ましくは50:1以下2:1以上)の範囲内であり、ならびに
オレフィン性C=C二重結合対イソシアヌレート基のモル比は100:1以下1:5以上(好ましくは70:1以下1:3以上、より好ましくは50:1以下2:1以上)の範囲内である。
および/または
イソシアヌレート三量化触媒が、酢酸カリウム、クラウンエーテルと組み合わせた酢酸カリウム、ポリエチレングリコールと組み合わせた酢酸カリウム、ポリプロピレングリコールと組み合わせた酢酸カリウム、オクタン酸スズ、ナトリウムフェノキシド、水酸化カリウム、トリオクチルホスフィン、および/またはトリブチルスズオキシドから選択されることが好ましい。
ここで、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下(好ましくは1:4以上4:1以下、より好ましくは1:3以上3:1以下)の範囲内であり、
NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上(好ましくは70:1以下1:1以上、より好ましくは50:1以下2:1以上)の範囲内であり、ならびに
オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上(好ましくは70:1以下1:3以上、より好ましくは50:1以下2:1以上)の範囲内であることが好ましい。
以下の実施例を参照しながら本発明をさらに詳細に説明するが、本発明をそれらに限定することを意図するものではない。
イソシアネート3:脂肪族ポリイソシアネート、低粘度HDI trimerisate(Desmodur(登録商標)N 3600 Covestro Deutschland AG)
イソシアネート4:イソホロンジイソシアネート(Desmodur(登録商標)I Covestro Deutschland AG)
イソシアネート5:ヘキサメチレンジイソシアネートに基づくポリエーテルの脂肪族で、ほぼ直鎖状イソシアネート官能性プレポリマー(Desmodur(登録商標)XP 2617 Covestro Deutschland AG)。
アクリレート2:イソボルニルアクリレート(Sigma-Aldrichから入手した分析用品質)
光開始剤1:ジフェニル(2,4,6-トリメチルベンゾイル)ホスフィンオキシド;TPO(Sigma-Aldrichから入手)
光開始剤2:2-ヒドロキシ-2-メチルプロピオフェノン;Darocur 1173(Sigma-Aldrichから入手)
抑制剤:BBOT:2,2’-(2,5-チオフェンジイル)ビス(5-(1,1-ジメチルエチル))ベンゾオキサゾール;UV遮断剤(Sigma-Aldrichから入手)
触媒:ジエチレングリコール中の酢酸カリウム+18-クラウン-6クラウンエーテル(Sigma-Aldrichから入手し、0.148gの酢酸カリウム+0.485gの18-クラウン-6エーテル+3.115gのジエチレングリコールの比率で混合した成分)。
本発明は一態様において以下を提供する。
[項目1]
前駆体から物体を製造する方法であって、以下の工程:
I)フリーラジカル架橋樹脂を担体の上に堆積させて、前記前駆体の第1の選択断面に対応する、前記担体に接合された構成材料の層を得る工程、
II)前記構成材料の先に施工された層の上にフリーラジカル架橋樹脂を堆積させて、前記前駆体のさらなる選択断面に対応する、先に施工された層に接合された前記構成材料のさらなる層を得る工程、
III)前記前駆体が形成されるまで工程II)を繰り返す工程、
を含み、
少なくとも工程II)におけるフリーラジカル架橋樹脂の堆積が、前記前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の選択された領域の露光および/または照射によって行われ、
前記フリーラジカル架橋性樹脂が、5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有し、
前記フリーラジカル架橋性樹脂が、NCO基およびオレフィン性C=C二重結合が存在する硬化性成分を含み、
前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下であること、ならびに
工程III)の後工程IV):
IV)工程III)の後に得られた前駆体を、前記得られた前駆体のフリーラジカル架橋樹脂中に存在するNCO基を少なくとも部分的にイソシアヌレート基に三量化するのに十分な条件下で処理して、物体を得る工程、
がさらに実施されることを特徴とする方法。
[項目2]
イソシアヌレート基が前記硬化性成分中にさらに存在し、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、前記硬化性成分において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内であることを特徴とする、項目1に記載の方法。
[項目3]
前記硬化性成分が、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であることを特徴とする、項目1または2に記載の方法。
[項目4]
前記硬化性成分が、イソシアヌレート基、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、
前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であり、
前記硬化性化合物において、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、ならびに
前記硬化性化合物において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内であることを特徴とする、項目3に記載の方法。
[項目5]
前記フリーラジカル架橋性樹脂がフリーラジカルスターターおよび/またはイソシアネート三量化触媒をさらに含む、項目1から4のいずれかに記載の方法。
[項目6]
少なくとも1種のフリーラジカルスターターが、α-ヒドロキシフェニルケトン、ベンジルジメチルケタール、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、ビス(4-メトキシベンゾイル)ジエチルゲルマニウムおよびそれらの少なくとも2種の任意の組み合わせの群から選択され、
および/または
イソシアヌレート三量化触媒が、酢酸カリウム、クラウンエーテルと組み合わせた酢酸カリウム、ポリエチレングリコールと組み合わせた酢酸カリウム、ポリプロピレングリコールと組み合わせた酢酸カリウム、オクタン酸スズ、ナトリウムフェノキシド、水酸化カリウム、トリオクチルホスフィン、および/またはトリブチルスズオキシドから選択されることを特徴とする、項目5に記載の方法。
[項目7]
前記樹脂において、NCO基対Zerewitinoff活性H原子のモル比が500以上であることを特徴とする、項目1~6のいずれかに記載の方法。
[項目8]
前記硬化性成分が、200g/モル以上5000g/モル以下の数平均分子量M n を有することを特徴とする、項目1~7のいずれかに記載の方法。
[項目9]
工程IV)における、工程III)の後に得られた前駆体を、前記得られた前駆体のフリーラジカル架橋樹脂中に存在するNCO基を少なくとも部分的にイソシアヌレート基に三量化するのに十分な条件下で処理する工程が、物体を60℃以上の温度に加熱する工程を含むことを特徴とする項目1~8のいずれかに記載の方法。
[項目10]
工程III)の後に得られた前駆体の表面および/または工程IV)の後に得られた物体の表面を、Zerewitinoff活性H原子を含む化合物と接触させ、前記前駆体および/または前記物体の周りの雰囲気中に天然の大気湿度として生じる水が排除されることを特徴とする、項目1~9のいずれかに記載の方法。
[項目11]
-前記担体が容器の内側に配置されており、重力の方向に垂直に下降可能である、
-前記容器が、少なくとも前記担体および前記担体の上に堆積した架橋樹脂を覆うのに十分な量の前記フリーラジカル架橋性樹脂を含む、
-各工程II)の前に、垂直方向に見て前記構成材料の最上層の上に前記フリーラジカル架橋性樹脂の層が形成されるように、前記担体を所定の距離だけ降下させる、
-工程II)において、エネルギービームが、前記前駆体の個々の選択断面に対応する前記フリーラジカル架橋性樹脂の層の選択された領域を露光および/または照射する、
ことを特徴とする、項目1~10のいずれかに記載の方法。
[項目12]
-前記担体が容器の内側に配置されており、重力の方向とは反対に垂直に上昇可能である、
-前記容器が前記フリーラジカル架橋性樹脂を提供する、
-各工程II)の前に、垂直方向に見て前記構成材料の最下層の下に前記フリーラジカル架橋性樹脂の層が形成されるように、前記担体を所定の距離だけ上昇させる、
-工程II)において、複数のエネルギービームが、前記前駆体の個々の選択断面に対応する前記フリーラジカル架橋性樹脂の層の選択された領域を同時に露光および/または照射する、
ことを特徴とする、項目1~10のいずれかに記載の方法。
[項目13]
-工程II)において、前記フリーラジカル架橋性樹脂が前記前駆体の個々の選択断面に対応する1または複数の印刷ヘッドから塗布され、その後露光および/または照射される、
ことを特徴とする、項目1~10のいずれかに記載の方法。
[項目14]
5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有するフリーラジカル架橋性樹脂の付加製造法における使用であって、
前記樹脂が、イソシアヌレート基、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、
NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であり、
前記硬化性化合物において、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、ならびに
前記硬化性化合物において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内である、
ことを特徴とする使用。
[項目15]
5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有する樹脂の架橋によって得ることができるポリマーであって、
前記樹脂が、NCO基およびオレフィン性C=C二重結合を含む硬化性成分含み、
NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内である、
ことを特徴とするポリマー。
Claims (15)
- 前駆体から物体を製造する方法であって、以下の工程:
I)フリーラジカル架橋樹脂を担体の上に堆積させて、前記前駆体の第1の選択断面に対応する、前記担体に接合された構成材料の層を得る工程、
II)前記構成材料の先に施工された層の上にフリーラジカル架橋樹脂を堆積させて、前記前駆体のさらなる選択断面に対応する、先に施工された層に接合された前記構成材料のさらなる層を得る工程、
III)前記前駆体が形成されるまで工程II)を繰り返す工程、
を含み、
少なくとも工程II)におけるフリーラジカル架橋樹脂の堆積が、前記前駆体の個々の選択断面に対応するフリーラジカル架橋性樹脂の選択された領域の露光および/または照射によって行われ、
前記フリーラジカル架橋性樹脂が、5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有し、
前記フリーラジカル架橋性樹脂がイソシアネート三量化触媒をさらに含み、
前記フリーラジカル架橋性樹脂が、NCO基およびオレフィン性C=C二重結合が存在する硬化性成分を含み、
前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下であること、ならびに
工程III)の後工程IV):
IV)工程III)の後に得られた前駆体を、前記得られた前駆体のフリーラジカル架橋樹脂中に存在するNCO基を少なくとも部分的にイソシアヌレート基に三量化するのに十分な条件下で処理して、物体を得る工程、
がさらに実施されることを特徴とする方法。 - イソシアヌレート基が前記硬化性成分中にさらに存在し、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、前記硬化性成分において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内であることを特徴とする、請求項1に記載の方法。
- 前記硬化性成分が、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であることを特徴とする、請求項1または2に記載の方法。
- 前記硬化性成分が、イソシアヌレート基、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、
前記硬化性化合物において、NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であり、
前記硬化性化合物において、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、ならびに
前記硬化性化合物において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内であることを特徴とする、請求項3に記載の方法。 - 前記フリーラジカル架橋性樹脂がフリーラジカルスターターをさらに含む、請求項1から4のいずれかに記載の方法。
- 少なくとも1種のフリーラジカルスターターが、α-ヒドロキシフェニルケトン、ベンジルジメチルケタール、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、ビス(4-メトキシベンゾイル)ジエチルゲルマニウムおよびそれらの少なくとも2種の任意の組み合わせの群から選択され、
および/または
イソシアヌレート三量化触媒が、酢酸カリウム、クラウンエーテルと組み合わせた酢酸カリウム、ポリエチレングリコールと組み合わせた酢酸カリウム、ポリプロピレングリコールと組み合わせた酢酸カリウム、オクタン酸スズ、ナトリウムフェノキシド、水酸化カリウム、トリオクチルホスフィン、および/またはトリブチルスズオキシドから選択されることを特徴とする、請求項5に記載の方法。 - 前記樹脂において、NCO基対Zerewitinoff活性H原子のモル比が500以上であることを特徴とする、請求項1~6のいずれかに記載の方法。
- 前記硬化性成分が、200g/モル以上5000g/モル以下の数平均分子量Mnを有することを特徴とする、請求項1~7のいずれかに記載の方法。
- 工程IV)における、工程III)の後に得られた前駆体を、前記得られた前駆体のフリーラジカル架橋樹脂中に存在するNCO基を少なくとも部分的にイソシアヌレート基に三量化するのに十分な条件下で処理する工程が、物体を60℃以上の温度に加熱する工程を含むことを特徴とする請求項1~8のいずれかに記載の方法。
- 工程III)の後に得られた前駆体の表面および/または工程IV)の後に得られた物体の表面を、Zerewitinoff活性H原子を含む化合物と接触させ、前記前駆体および/または前記物体の周りの雰囲気中に天然の大気湿度として生じる水が排除されることを特徴とする、請求項1~9のいずれかに記載の方法。
- -前記担体が容器の内側に配置されており、重力の方向に垂直に下降可能である、
-前記容器が、少なくとも前記担体および前記担体の上に堆積した架橋樹脂を覆うのに十分な量の前記フリーラジカル架橋性樹脂を含む、
-各工程II)の前に、垂直方向に見て前記構成材料の最上層の上に前記フリーラジカル架橋性樹脂の層が形成されるように、前記担体を所定の距離だけ降下させる、
-工程II)において、エネルギービームが、前記前駆体の個々の選択断面に対応する前記フリーラジカル架橋性樹脂の層の選択された領域を露光および/または照射する、
ことを特徴とする、請求項1~10のいずれかに記載の方法。 - -前記担体が容器の内側に配置されており、重力の方向とは反対に垂直に上昇可能である、
-前記容器が前記フリーラジカル架橋性樹脂を提供する、
-各工程II)の前に、垂直方向に見て前記構成材料の最下層の下に前記フリーラジカル架橋性樹脂の層が形成されるように、前記担体を所定の距離だけ上昇させる、
-工程II)において、複数のエネルギービームが、前記前駆体の個々の選択断面に対応する前記フリーラジカル架橋性樹脂の層の選択された領域を同時に露光および/または照射する、
ことを特徴とする、請求項1~10のいずれかに記載の方法。 - -工程II)において、前記フリーラジカル架橋性樹脂が前記前駆体の個々の選択断面に対応する1または複数の印刷ヘッドから塗布され、その後露光および/または照射される、
ことを特徴とする、請求項1~10のいずれかに記載の方法。 - 5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有するフリーラジカル架橋性樹脂の付加製造法における使用であって、
前記樹脂が、イソシアヌレート基、NCO基およびオレフィン性C=C二重結合を含む硬化性化合物を含み、
NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内であり、
前記硬化性化合物において、NCO基対イソシアヌレート基のモル比が、100:1以下1:2以上の範囲内であり、ならびに
前記硬化性化合物において、オレフィン性C=C二重結合対イソシアヌレート基のモル比が100:1以下1:5以上の範囲内である、
ことを特徴とする使用。 - 5mPa・s以上100000mPa・s以下の粘度(23℃、DIN EN ISO 2884-1)を有する樹脂の架橋によって得ることができるポリマーであって、
前記架橋は、C=C二重結合のフリーラジカル架橋と、それに続くイソシアヌレート基を得るNCO基の三量化からなる二段階法を介して行われ、
前記樹脂が、NCO基およびオレフィン性C=C二重結合を含む硬化性成分含み、
NCO基対オレフィン性C=C二重結合のモル比が、1:5以上5:1以下の範囲内である、
ことを特徴とするポリマー。
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US20190367666A1 (en) | 2019-12-05 |
CN114874411A (zh) | 2022-08-09 |
JP2019535554A (ja) | 2019-12-12 |
KR20190086447A (ko) | 2019-07-22 |
CN110023368A (zh) | 2019-07-16 |
US20200190245A1 (en) | 2020-06-18 |
WO2018087395A1 (de) | 2018-05-17 |
US20190367665A1 (en) | 2019-12-05 |
US20190337224A1 (en) | 2019-11-07 |
EP3538585A1 (de) | 2019-09-18 |
WO2018087399A1 (de) | 2018-05-17 |
WO2018087396A1 (de) | 2018-05-17 |
KR102388093B1 (ko) | 2022-04-20 |
CN109923143B (zh) | 2022-04-22 |
CN109923142A (zh) | 2019-06-21 |
US10449714B2 (en) | 2019-10-22 |
EP3538584B1 (de) | 2020-08-26 |
WO2018087382A1 (de) | 2018-05-17 |
EP3538583A1 (de) | 2019-09-18 |
EP3538584A1 (de) | 2019-09-18 |
CN109923143A (zh) | 2019-06-21 |
EP3538586A1 (de) | 2019-09-18 |
US20180133953A1 (en) | 2018-05-17 |
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