JP7440185B2 - 印刷に好適な樹脂組成物および印刷方法 - Google Patents
印刷に好適な樹脂組成物および印刷方法 Download PDFInfo
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- JP7440185B2 JP7440185B2 JP2021525371A JP2021525371A JP7440185B2 JP 7440185 B2 JP7440185 B2 JP 7440185B2 JP 2021525371 A JP2021525371 A JP 2021525371A JP 2021525371 A JP2021525371 A JP 2021525371A JP 7440185 B2 JP7440185 B2 JP 7440185B2
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Classifications
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- C—CHEMISTRY; METALLURGY
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F238/00—Copolymers of compounds having one or more carbon-to-carbon triple bonds
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- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
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- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
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- B29C64/129—Processes of additive manufacturing using only liquids or viscous materials, e.g. depositing a continuous bead of viscous material using layers of liquid which are selectively solidified characterised by the energy source therefor, e.g. by global irradiation combined with a mask
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Description
-イオン性光酸発生剤、特に、
・対イオンとしてBF4 -、SbF6 -、AsF6 -、B(C6F5)4 -、またはPF6 -などのハロゲン化錯体を含有するオニウム塩、例えば、アリルジアゾニウム、ジアリールヨードニウム(例えば、The Dow Chemical Companyから入手可能なCyracure UVI-6976、Lamberti SpAから入手可能なEsacure 1064、CHANGZHOU TRONLY NEW ELECTRONIC MATERIALS CO.,LTDから入手可能なQL Cure 211)、トリアリールスルホニウム(例えば、IGM Resins B.V.から入手可能なOmnicat 440、BASF SEから入手可能なIrgacure 250、Rhodiaから入手可能なRhodorsil 207)、トリアリールセレノニウムまたはトリアリールホスホニウム塩のオニウム塩、
・対イオンとしてBF4 -、SbF6 -、AsF6 -、B(C6F5)4 -、またはPF6 -などのハロゲン化錯体を含有する鉄アレーン錯体(例えば、BASF SEから入手可能なIrgacure 261)、
・対イオンとしてBF4 -、SbF6 -、AsF6 -、B(C6F5)4 -、またはPF6 -などのハロゲン化錯体を含有するジアルキルフェナシルスルホニウム塩、
-非イオン性光酸発生剤、特に、
・カルボン酸の2-ニトロベンジルエステル、
・スルホン酸の2-ニトロベンジルエステル、
・UV照射するとスルフィン酸を生成するスルホン化合物、
・トリアリールホスフェート、
・N-ヒドロキシイミドスルホネート(例えば、N-ヒドロキシ-5-ノルボルネン-2,3-ジカルボキシイミドパーフルオロ-1-ブタンスルホネート)、
・フェノールのスルホン酸エステル、
・ジアゾナフトキノン、
・イミノスルホネート、
・トリクロロメチル-1,3,5-トリアジン(例えば、2-(4-メトキシスチリル)-4,6-ビス(トリクロロメチル)-1,3,5-トリアジン)、および/または上記のうちのいずれか1つの混合物が挙げられる。
-カルバメート(例えば、m-ニトロフェニル、3,5-ジメトキシベンジル、1-メチル-1-(3,5-ジメトキシフェニル)エチル、α-メチルニトロピペロニル、o-ニトロベンジル、3,4-ジメトキシ-6-ニトロベンジル、フェニル(o-ニトロフェニル)メチル、2-(2-ニトロフェニル)エチル、6-ニトロベラトリル、4-メトキシフェナシル)、3'5'-ジメトキシベンゾインカルバメート)、
-o-アシルオキシム、
-アンモニウム塩、
-スルホアミド、
-ホルムアミド、
-ニフェジピン、
-アミネイミド、
-α-アミノケトン
-カルバモイルオキシウム、および/または上記のうちのいずれか1つの混合物が挙げられる。
zは2~1000の整数を表し、
Zは、各出現において互いから独立して、水素またはチオール保護基を表し、
Lは、各出現において互いから独立して、直鎖または分岐、飽和または不飽和、置換または非置換のアルキレン基;直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキレン基;飽和または不飽和、置換または非置換のシクロアルキレン基;飽和または不飽和、置換または非置換のヘテロシクロアルキレン基;置換または非置換のアリーレン基;置換または非置換のヘテロアリーレン基;直鎖または分岐、置換または非置換のアラルキレン基;直鎖または分岐、置換または非置換のアルカリレン基;またはケイ素含有二価基からなる群から選択される単結合または二価基を表し、
Xは、直鎖または分岐、飽和または不飽和、置換または非置換のアルキル基;直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキル基;飽和または不飽和、置換または非置換のシクロアルキル基;飽和または不飽和、置換または非置換のヘテロシクロアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基;直鎖または分岐、置換または非置換のアラルキル基;直鎖または分岐、置換または非置換のアルカリル基;ケイ素含有z価基からなる群から選択されるz価基を表す。
実施例1
様々な3D印刷構造体の靱性を、ISO規格179-1:2010に従ってCharpy衝撃試験により決定した。使用した樹脂は、チオールモノマー(例えば、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)、PETMP)、およびアルキンモノマー(例えば、1,4-ブタンジオールジブト-1-イニルエーテル、Bbut;ジ(ブト-3-イン-1-イル)カーボネート、DBC(登録商標))、および/またはアリルモノマー(ジアリル(2,2,4-トリメチルヘキサン-1,6-ジイル)ジカルバメート)、および/またはメタクリレート(例えば、1,4-ブタンジオールジメタクリレート、BMA;イソブチルメタクリレート、IsobutylMA;7,7,9-トリメチル-4,13-ジオキソ-3,14-ジオキサ-5,12-ジアザヘキサデカン-1,16-ジイルビス(2-メタクリレート)、UDMA)、および/またはアクリレート(1,4-ブタンジオールジアクリレート、BA)を含む。配合物に、3重量%のIrgacure TPO-L(IrgTPOL)、0.5重量%のピロガロール、2重量%のMiramerA99、0.05重量%のスーダンオレンジを添加した。印刷サンプルを405nmで100℃で後硬化した。参照材料として、BMAおよびBAそれぞれ、ならびに3重量%のIrgTPOLを含むPETMP/アルケン配合物を使用した。モノマーの官能基の比率は、表1において括弧の中に列挙されている。
[表1]
ISO 75-1:1993およびISO 75-2:1993に従って、様々な3D印刷構造体の加熱撓み温度(HDT)を決定した(貫層方向の位置において方法Bにより試験した)。使用した樹脂は、チオールモノマー(例えば、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)、PETMP)、および/またはアルキンモノマー(例えば、1,4-ブタンジオールジブト-1-イニルエーテル、Bbut;ジ(ブト-3-イン-1-イル)カーボネート、DBC(登録商標);ジ(プロパ-2-イン-1-イル)カーボネート、DPC;ジ(ブト-3-イン-1-イル)(2,2,4-トリメチルヘキサン-1,6-ジイル)ジカルバメート)、および/またはアリルモノマー(ジアリル(2,2,4-トリメチルヘキサン-1,6-ジイル)ジカルバメート)、および/またはメタクリレート(例えば、1,4-ブタンジオールジメタクリレート、BMA;イソブチルメタクリレート、IsobutylMA;7,7,9-トリメチル-4,13-ジオキソ-3,14-ジオキサ-5,12-ジアザヘキサデカン-1,16-ジイルビス(2-メタクリレート)、UDMA;ネオペンチルグリコールジメタクリレート、NPGDMA;トリメチロールプロパントリメタクリレート、TMPTMA)、および/またはアクリレート(1,4-ブタンジオールジアクリレート、BA)、および/またはビニルエーテル(1,4-ビス(ビニルオキシ)ブタン、BuVE)を含む。配合物に、3重量%のIrgacure TPO-L(IrgTPOL)、0.5重量%のピロガロール、2重量%のMiramerA99、0.05重量%のスーダンオレンジを添加した。印刷サンプルを405nmで100℃で後硬化した。さらなる参照材料として、BMAおよびBAそれぞれ、ならびにまた、3重量%のIrgTPOLを含むチオール-エンおよびチオール-イン配合物(PETMP/Bbut、PETMP/BuVE)を使用した。
[表2]
メタクリレートモノマー(グリセリルジメタクリレート、GMA)、アルキンモノマー(ジ(プロパ-2-イン-1-イル)カーボネート、DPC)、およびチオールモノマー(ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)、PETMP)を含有する配合物の安定性に対する、0.5重量%のピロガロール(PY)、または/および2重量%のMiramer A99(MA99)、または/および0.05重量%の芳香族アゾ化合物の効果を、レオロジー測定により調べた。配合物を70℃で3日間貯蔵した。粘度の増加を24時間ごとに監視した。
[表3]
U-2OS骨肉腫細胞を用いて様々な3D印刷構造体の表面への細胞の結合を決定した。(無毒の)陰性対照として細胞培養プレートを使用した。空気大気+5%のCO2中、37±1℃で、175cm2の培養フラスコ(Costar Corning)内で、McCoy's 5A培地(Thermo Fisher Scientific)、10%のウシ胎児血清(Gibco)、2mMのL-グルタミン、1%のペニシリン/ストレプトマイシン中で細胞を培養し、所定の間隔で継代培養した。3*105個のU-2OS細胞をウェルあたり500μLで12ウェルプレートに、および同じ大きさの様々な3D印刷構造体の表面上に播種した。
[表4]
MRC-5細胞を使用して、ISO規格10993-5:2009に従って3D印刷構造体の細胞傷害性を評価した。37±1℃および5%のCO2で、175cm2の培養フラスコ(Costar Corning)内で、Minimal Essential Medium(MEM、Life technologies)およびアール塩、10%のウシ胎児血清(Gibco)、2mMのL-グルタミン、1%のペニシリン/ストレプトマイシン中でMRC-5細胞を培養した。この細胞株は、14週齢の雄の胎児の正常な肺組織に由来した。ISO10993-1ガイドラインに従って、37℃で24時間、細胞培養培地中で印刷サンプルを抽出した。サブコンフルエントな培養物を得るために、サンプルの溶出液に曝す24時間前に、ウェルおよび培養物あたり8000個のMRC-5細胞を播種した。(有毒な)陽性対照として、トリトンX100をMRC-5細胞に10分間添加した。(無毒の)陰性対照として、細胞培養培地を使用した。
[表5]
塩基性条件下でチオールのマイケル付加反応を使用して、選択された組成物を抗菌性アクリレートモノマー(N,N-ジメチル-N-(4-メチレンヘキシ-5-エン-1-イル)ヘキサデカン-1-アミニウム、DMHA)で修飾した。したがって、室温で24時間、DMHAの飽和エタノール溶液中で3D印刷構造体をインキュベートした。20mLの溶液に0.2mLのトリメチルアミンを添加した。その後、サンプルをエタノールで洗浄し、50℃で6時間乾燥させた。
チオールモノマー(ペンタエリトリトールテトラキス(3-メルカプトプロピオネート))と、末端C=C二重結合を含有するモノマーまたは末端アルキン基を含有するモノマーのいずれかとを含有する配合物の安定性に対する、0.5重量%のピロガロール(PY)、および/または2重量%のMiramer A99(MA99)および/または0.05重量%の芳香族アゾ化合物の効果を、レオロジー測定によって調べた。配合物を50℃で7日間貯蔵した。1日目、3日目、および7日目に粘度の増加を監視した。
[表7]
チオールモノマー(ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)[PETMP])と、末端C=C二重結合を含有するモノマー(1,4-ブタンジオールジメタクリレート[BMA]、もしくは1,3,5-トリアリル-1,3,5-トリアジン-2,4,6-(1H,3H,5H-トリオン)、および/または末端アルキン基を含有するモノマー(ジ(プロパ-2-イン-1-イル)カーボネート[DPC])とを含有する配合物の安定性に対する、0.5重量%のラジカル捕捉剤(ピロガロール[Py]または没食子酸プロピル[PYG]または2,4-ジヒドロキシベンゾアルデヒド[2,4-DHB]または3,4-ジヒドロキシベンゾアルデヒド[3,4-DHB]または3,5-ジヒドロキシベンゾアルデヒド[3,5-DHB]または2,5-ジヒドロキシベンゾアルデヒド[2,5-DHB]または2,3-ジヒドロキシベンゾアルデヒド[2,3-DHB]または2,3,4-トリヒドロキシベンゾアルデヒド[2,3,4-THB])、および/または2重量%のMiramer A99(MA99)、および/または0.05重量%の錯化剤(スーダンIIまたはシュウ酸アンモニウム[AO]またはエチレンビス(ジフェニルホスフィン)[EBP])の効果を、レオロジー測定によって調べた。配合物を50℃で42日間貯蔵した。42日後に粘度の増加を監視した。
[表8]
フォトポリマーの加水分解劣化挙動の評価のために、3D印刷試料を用意した(4×4×1mm3)。使用した樹脂は、チオールモノマー(例えば、ペンタエリトリトールテトラキス(3-メルカプトプロピオネート)、PETMP)、アルキンモノマー(例えば、1,4-ブタンジオールジブト-1-イニルエーテル、Bbut)、およびメタクリレート(例えば、1,4-ブタンジオールジメタクリレート、BMA)からなる。配合物に、3重量%のIrgacure TPO-L(IrgTPOL)、0.5重量%のピロガロール、2重量%のMiramerA99、0.05重量%のスーダンオレンジを添加した。印刷サンプルを405nmで100℃で後硬化した。参照材料として、3重量%のIrgTPOLと共に、BMAおよびBAそれぞれを使用した。
[表9]
NIR光源およびCaF2ビームスプリッタを使用して、Bruker Vertex 80 FTIR分光計と連結されたAnton Paar MCR 302 WESPレオメータで偏光流性測定を実施した。IRビームをサンプルを通してガイドし、これを外部ミラーを用いてレオロジーによって分析した。レオメータは、P-PTD200/GLペルチェガラスプレートおよびPP25測定システムを備え、これは、IRビームを外部MCT検出器内に反射させる。チオール/イン/エン材料のガラス表面への良好な接着に起因して、測定設定の保護のためにサンプルとガラスプレートとの間にPEテープを設置した。
[表10]
洗浄効率、およびしたがって印刷構造体からの残留非硬化UV樹脂の除去の評価のために、以下の試験を実行した。
[項目1]
樹脂組成物であって、
少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1と、
少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2と、
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3と、
少なくとも1つの光開始剤と、
少なくとも1つの安定化剤とを含む、
樹脂組成物。
[項目2]
少なくとも1つの化合物C1が、少なくとも1つの末端アルキン官能基と、直鎖または分岐、飽和または不飽和、置換または非置換のアルキル基;直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキル基;飽和または不飽和、置換または非置換のシクロアルキル基;飽和または不飽和、置換または非置換のヘテロシクロアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基;直鎖または分岐、置換または非置換のアラルキル基;直鎖または分岐、置換または非置換のアルカリル基;オリゴマーまたはポリマーから選択される少なくとも1つの官能基と、を有する、項目1に記載の樹脂組成物。
[項目3]
少なくとも1つの化合物C1が、プロパルギル、ブチニル、およびペンチニルからなる群から選択される少なくとも1つの末端アルキン官能基を有する、項目1または2に記載の樹脂組成物。
[項目4]
少なくとも1つの化合物C1が、少なくとも1つの末端アルキン官能基と、カーボネート、カルバメート、エーテル、およびエステルからなる群から選択される少なくとも1つの官能基とを有する、項目1から3のいずれか一項に記載の樹脂組成物。
[項目5]
少なくとも1つの化合物C1が、プロパルギルカーボネート、プロパルギルカルバメート、プロパルギルエーテル、プロパルギルエステル、ブチニルカーボネート、ブチニルカルバメート、ブチニルエーテル、ブチニルエステル、ペンチニルカーボネート、ペンチニルカルバメート、ペンチニルエーテル、およびペンチニルエステルからなる群から選択される官能基を有する化合物を含む、項目1から4のいずれか一項に記載の樹脂組成物。
[項目6]
少なくとも1つの化合物C1が、1つの末端アルキン官能基を有する、項目1から5のいずれか一項に記載の樹脂組成物。
[項目7]
少なくとも1つの化合物C1が、少なくとも2つの末端アルキン官能基を有する、項目1から5のいずれか一項に記載の樹脂組成物。
[項目8]
チオール官能基のうちの少なくとも1つがチオール保護基を含む、項目1から7のいずれか一項に記載の樹脂組成物。
[項目9]
チオール保護基が、アシル基、シリル基、およびシロキシル基からなる群から選択される、項目8に記載の樹脂組成物。
[項目10]
樹脂組成物が、少なくとも1つの光酸および/または少なくとも1つの光塩基をさらに含む、項目8または9に記載の樹脂組成物。
[項目11]
少なくとも1つの化合物C2が、以下の一般式(XIII)により表され、
[化13]
式中、
zは2から1000の整数を表し、
Zは、各出現において互いから独立して、水素またはチオール保護基を表し、
Lは、各出現において互いから独立して、直鎖または分岐、飽和または不飽和、置換または非置換のアルキレン基;直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキレン基;飽和または不飽和、置換または非置換のシクロアルキレン基;飽和または不飽和、置換または非置換のヘテロシクロアルキレン基;置換または非置換のアリーレン基;置換または非置換のヘテロアリーレン基;直鎖または分岐、置換または非置換のアラルキレン基;直鎖または分岐、置換または非置換のアルカリレン基;またはケイ素含有二価基からなる群から選択される単結合または二価基を表し、
Xは、直鎖または分岐、飽和または不飽和、置換または非置換のアルキル基;直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキル基;飽和または不飽和、置換または非置換のシクロアルキル基;飽和または不飽和、置換または非置換のヘテロシクロアルキル基;置換または非置換のアリール基;置換または非置換のヘテロアリール基;直鎖または分岐、置換または非置換のアラルキル基;直鎖または分岐、置換または非置換のアルカリル基;またはケイ素含有z価基からなる群から選択されるz価基を表す、
項目1から10のいずれか一項に記載の樹脂組成物。
[項目12]
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3が、ビニル官能基、アリル官能基、アクリレート官能基、およびメタクリレート官能基からなる群から選択される少なくとも1つの官能基を有する、項目1から11のいずれか一項に記載の樹脂組成物。
[項目13]
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3が、少なくとも1つのビニル官能基および/またはアリル官能基を有する、項目12に記載の樹脂組成物。
[項目14]
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3が、少なくとも1つの(メタ)アクリレート官能基を有する、項目12または13に記載の樹脂組成物。
[項目15]
少なくとも1つの化合物C3が、少なくとも2つの炭素-炭素二重結合、特に、ビニル官能基、アリル官能基、アクリレート官能基、およびメタクリレート官能基からなる群から選択される少なくとも2つの官能基を有する、項目1から14のいずれか一項に記載の樹脂組成物。
[項目16]
樹脂組成物が、5~80重量%の少なくとも1つの化合物C1を含む、項目1から15のいずれか一項に記載の樹脂組成物。
[項目17]
樹脂組成物が、5~80重量%の少なくとも1つの化合物C2を含む、項目1から16のいずれか一項に記載の樹脂組成物。
[項目18]
樹脂組成物が、10~90重量%の少なくとも1つの化合物C3を含む、項目1から17のいずれか一項に記載の樹脂組成物。
[項目19]
光開始剤が、紫外線活性光開始剤および/または可視光活性光開始剤である、項目1から18のいずれか一項に記載の樹脂組成物。
[項目20]
樹脂組成物が、0.1~20重量%の少なくとも1つの光開始剤を含む、項目1から19のいずれか一項に記載の樹脂組成物。
[項目21]
少なくとも1つの安定化剤が、少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤を含む、項目1から20のいずれか一項に記載の樹脂組成物。
[項目22]
少なくとも1つの安定化剤が、少なくとも1つのリン含有化合物、特に、少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体を含む、項目1から21のいずれか一項に記載の樹脂組成物。
[項目23]
少なくとも1つの安定化剤が、少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物、より具体的にはアゾ基に対するオルト位にヒドロキシ基を有する少なくとも1つの芳香族アゾ化合物を含む、項目1から22のいずれか一項に記載の樹脂組成物。
[項目24]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つのリン含有化合物、特に少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体とを含む、
項目1から23のいずれか一項に記載の樹脂組成物。
[項目25]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物と、を含む、
項目1から23のいずれか一項に記載の樹脂組成物。
[項目26]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つのリン含有化合物、特に、少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体と、
少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物と、を含む、
項目1から25のいずれか一項に記載の樹脂組成物。
[項目27]
樹脂組成物が、0.001~10重量%の少なくとも1つの安定化剤を含む、項目1から26のいずれか一項に記載の樹脂組成物。
[項目28]
樹脂組成物が、顔料、無機充填剤、有機充填剤、分散剤、レベリング剤、スリップ剤、光吸収体、レオロジー改質剤、および消泡添加剤からなる群から選択される少なくとも1つの添加剤をさらに含む、項目1から27のいずれか一項に記載の樹脂組成物。
[項目29]
樹脂組成物が、0.1~70重量%の少なくとも1つの添加剤を含む、項目28に記載の樹脂組成物。
[項目30]
樹脂組成物が、実質的に溶媒を含まず、特に、実質的に水を含まない、項目1から29のいずれか一項に記載の樹脂組成物。
[項目31]
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3が、アリル官能基、アクリレート官能基、およびメタクリレート官能基からなる群から選択される少なくとも1つの官能基を有し、
樹脂組成物が、実質的に溶媒を含まず、特に、実質的に水を含まない、
項目1から30のいずれか一項に記載の樹脂組成物。
[項目32]
少なくとも1つの化合物C1および少なくとも1つの化合物C3が、少なくとも1つの末端アルキン官能基と少なくとも1つの炭素-炭素二重結合とを有する1つの化合物C4を形成する、項目1から31のいずれか一項に記載の樹脂組成物。
[項目33]
項目1から32のいずれか一項に記載の樹脂組成物の、インクとしての使用。
[項目34]
少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1と、
少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2と、
少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3と、
少なくとも1つの光開始剤と、
任意で少なくとも1つの安定化剤とを含む、
キット、特に、パーツキット。
[項目35]
インクとしての使用、またはインクにおける使用のための樹脂組成物を調製するための、項目34に記載のキットの使用。
[項目36]
少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1と、少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3とを含む第1のインク部分を提供する段階と、
少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2を含む第2のインク部分を提供する段階であって、
第1のインク部分および第2のインク部分のうちの少なくとも1つが、少なくとも1つの光開始剤をさらに含む、提供する段階と、
第1のインク部分および第2のインク部分から樹脂組成物を形成し、すぐ後に、樹脂組成物の少なくとも一部にエネルギー搬送活性ビームを照射して、樹脂組成物の少なくとも一部の重合を引き起こして、ポリマーを得る段階と、を含む、
印刷方法。
[項目37]
第1のインク部分と第2のインク部分のうちの少なくとも1つが、少なくとも1つの安定化剤をさらに含む、項目36に記載の印刷方法。
[項目38]
印刷方法が、
特に第1のインク部分および/または第2のインク部分を提供する前および/または提供する際に、第1のインク部分および/または第2のインク部分を加熱する段階をさらに含む、項目36または37に記載の印刷方法。
[項目39]
項目1から32のいずれか一項に記載の樹脂組成物を提供する段階と、
樹脂組成物の少なくとも一部にエネルギー搬送活性ビームを照射して、樹脂組成物の少なくとも一部の重合を引き起こして、ポリマーを得る段階とを含む、印刷方法。
[項目40]
印刷方法が、
特に、樹脂組成物を提供する前および/または提供する際に、樹脂組成物を加熱する段階をさらに含む、項目39に記載の印刷方法。
[項目41]
印刷方法が、三次元印刷方法である、項目36から40のいずれか一項に記載の印刷方法。
[項目42]
三次元印刷方法が、光造形法(SLA)、二光子吸収(TPA)重合、デジタルライトプロセッシング(DLP)、反応性レーザ焼結(RLS)、ソリッドグラウンド硬化(SGC)、マルチジェットモデリング(MJM)、またはそれらの組み合わせからなる群から選択されるいずれか1つである、項目41に記載の印刷方法。
[項目43]
樹脂組成物の少なくとも一部を照射している間および/または照射した後に、ポリマーを後硬化する段階をさらに含む、項目36から42のいずれか一項に記載の印刷方法。
[項目44]
エネルギー搬送活性ビームが、特に紫外線照射および可視光照射からなる群から選択される電磁放射線を含む、項目36から43のいずれか一項に記載の印刷方法。
[項目45]
印刷方法が、溶媒を用いない印刷方法である、項目36から44のいずれか一項に記載の印刷方法。
[項目46]
ポリマーを洗浄する段階をさらに含む、項目36から45のいずれか一項に記載の印刷方法。
[項目47]
洗浄する段階が、ポリマーを、アルカリ化合物、界面活性剤、および適切な溶媒を含む洗浄組成物と接触させることを含む、項目46に記載の印刷方法。
[項目48]
項目36から47のいずれか一項に記載の印刷方法によって得ることができる、ポリマー。
[項目49]
項目48に記載のポリマーを含む、またはそれから形成される、物品。
[項目50]
物品が、特にインプラント、代用骨、代用組織、および歯科用製品からなる群から選択される、医療用または生物医学用デバイスである、項目49に記載の物品。
[項目51]
物品の表面が、コーティング、特に抗菌コーティングにより改質されている、項目49または50に記載の物品。
[項目52]
物品が、形状記憶物品である、項目49から51のいずれか一項に記載の物品。
[項目53]
医療または生物医学用途における、項目48に記載のポリマーの、または項目49から52のいずれか一項に記載の物品の使用。
[項目54]
医療または生物医学用途が、移植、代用骨または置換、代用組織または置換、および歯科用途からなる群から選択されるいずれか1つを含む、項目53に記載の使用。
[項目55]
少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1および/または少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3と、
少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2と、
ラジカル捕捉剤、リン含有化合物、および錯化剤からなる群から選択される少なくとも1つの安定化剤とを備える、組成物。
[項目56]
少なくとも1つの安定化剤が、少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤を含む、項目55に記載の組成物。
[項目57]
少なくとも1つの安定化剤が、少なくとも1つのリン含有化合物、特に、少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体を含む、項目55または56に記載の組成物。
[項目58]
少なくとも1つの安定化剤が、少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物、より具体的にはアゾ基に対するオルト位にヒドロキシ基を有する少なくとも1つの芳香族アゾ化合物を含む、項目55から57のいずれか一項に記載の組成物。
[項目59]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つのリン含有化合物、特に少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体とを含む、
項目55から58のいずれか一項に記載の組成物。
[項目60]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物と、を含む、
項目55から58のいずれか一項に記載の組成物。
[項目61]
少なくとも1つの安定化剤が、
少なくとも1つのラジカル捕捉剤、特に少なくとも1つのフェノール系ラジカル捕捉剤と、
少なくとも1つのリン含有化合物、特に、少なくとも1つのホスホン酸、および/または少なくとも1つのリン酸、および/またはそれらの誘導体と、
少なくとも1つの錯化剤、特に少なくとも1つの芳香族アゾ化合物と、を含む、
項目55から60のいずれか一項に記載の組成物。
[項目62]
樹脂組成物を提供する段階であって、樹脂組成物が、
(i)少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1および/または少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3と、
(ii)少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2とを含む、提供する段階と、
樹脂組成物の少なくとも一部にエネルギー搬送活性ビームを照射して、樹脂組成物の少なくとも一部の重合を引き起こして、ポリマーを得る段階と、
ポリマーを、アルカリ化合物、界面活性剤、および溶媒を含む洗浄組成物と接触させる段階とを含む、印刷方法。
[項目63]
ポリマーを洗浄組成物と接触させる段階が、20℃~60℃の温度で、かつ/または超音波の適用の際に実行される、項目62に記載の印刷方法。
[項目64]
アルカリ化合物が、無機アルカリ化合物および/または有機アルカリ化合物を含む、項目62または63に記載の印刷方法。
[項目65]
アルカリ化合物が、アルカリ金属炭酸塩、アルカリ金属水酸化物、水酸化アンモニウム、アンモニア、アンモニウム誘導体、エタノールアミンなどの有機アミン、およびそれらの組み合わせからなる群から選択される、項目62から64のいずれか一項に記載の印刷方法。
[項目66]
界面活性剤が、アニオン界面活性剤、双性イオン界面活性剤、両性界面活性剤、非イオン界面活性剤、一価カチオン界面活性剤などのカチオン界面活性剤、およびそれらの組み合わせからなる群から選択される、項目62から65のいずれか一項に記載の印刷方法。
[項目67]
溶媒が、極性溶媒および/または無極性溶媒を含む、項目62から66のいずれか一項に記載の印刷方法。
[項目68]
溶媒が、水、アルコール、エーテル、エステル、カーボネート、ハロゲン化アルカン、ニトリル、アルデヒド、ケトン、アミド溶媒、スルホキシド、酸、炭化水素、芳香族溶媒、及びそれらの組み合わせからなる群から選択される、項目62から67のいずれか一項に記載の印刷方法。
[項目69]
印刷方法が、ポリマーを洗浄組成物と接触させる段階の後に、洗浄組成物から固体を除去する段階をさらに含む、項目62から68のいずれか一項に記載の印刷方法。
[項目70]
洗浄組成物から固体を除去する段階が、洗浄組成物の濾過、遠心分離、および/またはデカンテーションのうちの少なくとも1つを含む、項目69に記載の印刷方法。
Claims (9)
- 少なくとも1つの末端アルキン官能基を有する少なくとも1つの化合物C1および/または少なくとも1つの炭素-炭素二重結合を有する少なくとも1つの化合物C3と、
少なくとも2つのチオール官能基を有する少なくとも1つの化合物C2と、
ラジカル捕捉剤及びリン含有化合物を含み、前記リン含有化合物がホスホン酸及び/又はリン酸及び/又はそのエステルを含む、少なくとも1つの安定化剤と、少なくとも1つの光開始剤と、を備える、樹脂組成物を提供する段階と、
前記樹脂組成物の少なくとも一部にエネルギー搬送活性ビームを照射し、前記樹脂組成物の前記少なくとも一部の重合を引き起こしてポリマーを得て、前記ポリマーが歯科用製品の形態である、段階と、を含む、印刷方法。 - 前記少なくとも1つの化合物C1が、
少なくとも1つの末端アルキン官能基と、直鎖または分岐、飽和または不飽和、置換または非置換のアルキル基、直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキル基、飽和または不飽和、置換または非置換のシクロアルキル基、飽和または不飽和、置換または非置換のヘテロシクロアルキル基、置換または非置換のアリール基、置換または非置換のヘテロアリール基、直鎖または分岐、置換または非置換のアラルキル基、直鎖または分岐、置換または非置換のアルカリル基、オリゴマーまたはポリマーから選択される少なくとも1つと、および/または、
プロパルギル、ブチニル、およびペンチニルからなる群から選択される少なくとも1つの末端アルキン官能基を有するか、および/または、
少なくとも1つの末端アルキン官能基と、カーボネート、カルバメート、エーテル、およびエステルからなる群から選択される少なくとも1つの官能基とを有するか、および/または、
プロパルギルカーボネート、プロパルギルカルバメート、プロパルギルエーテル、プロパルギルエステル、ブチニルカーボネート、ブチニルカルバメート、ブチニルエーテル、ブチニルエステル、ペンチニルカーボネート、ペンチニルカルバメート、ペンチニルエーテル、およびペンチニルエステルからなる群から選択される官能基を有する化合物であるか、および/または、
1つの末端アルキン官能基、もしくは少なくとも2つの末端アルキン官能基を有する、という特徴のうちの少なくとも1つを含む、請求項1に記載の印刷方法。 - 前記少なくとも1つの化合物C2が、以下の一般式(XIII)により表され、
zは2から1000の整数を表し、
Zは、各出現において互いから独立して、水素またはチオール保護基を表し、
Lは、各出現において互いから独立して、直鎖または分岐、飽和または不飽和、置換または非置換のアルキレン基、直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキレン基、飽和または不飽和、置換または非置換のシクロアルキレン基、飽和または不飽和、置換または非置換のヘテロシクロアルキレン基、置換または非置換のアリーレン基、置換または非置換のヘテロアリーレン基、直鎖または分岐、置換または非置換のアラルキレン基、直鎖または分岐、置換または非置換のアルカリレン基、またはケイ素含有二価基からなる群から選択される単結合または二価基を表し、
Xは、直鎖または分岐、飽和または不飽和、置換または非置換のアルキル基、直鎖または分岐、飽和または不飽和、置換または非置換のヘテロアルキル基、飽和または不飽和、置換または非置換のシクロアルキル基、飽和または不飽和、置換または非置換のヘテロシクロアルキル基、置換または非置換のアリール基、置換または非置換のヘテロアリール基、直鎖または分岐、置換または非置換のアラルキル基、直鎖または分岐、置換または非置換のアルカリル基、またはケイ素含有z価基からなる群から選択されるz価基を表す、
請求項1または2に記載の印刷方法。 - 前記少なくとも1つの化合物C3が、
ビニル官能基、アリル官能基、アクリレート官能基、およびメタクリレート官能基からなる群から選択される少なくとも1つの官能基を有するか、および/または、
少なくとも2つの炭素-炭素二重結合を有する、という特徴のうちの少なくとも1つを含む、請求項1から3のいずれか一項に記載の印刷方法。 - 前記樹脂組成物が、少なくとも1つの(メタ)アクリレート官能基を有する化合物C3a、および少なくとも1つのアリル官能基を有する化合物C3bを含む、少なくとも2つの化合物C3を有する、請求項1から4のいずれか一項に記載の印刷方法。
- 前記少なくとも1つの安定化剤が、少なくとも1つの錯化剤をさらに含む、請求項1から5のいずれか一項に記載の印刷方法。
- 前記樹脂組成物が、
前記少なくとも1つの光開始剤は、紫外線活性光開始剤および/または可視光活性光開始剤を含むか、および/または、
前記樹脂組成物は0.001~10重量%の少なくとも1つの安定化剤を含むか、および/または、
前記樹脂組成物は顔料、無機充填剤、有機充填剤、分散剤、レベリング剤、スリップ剤、光吸収体、レオロジー改質剤、および消泡添加剤からなる群から選択される少なくとも1つの添加剤をさらに含むか、および/または、
前記樹脂組成物は、実質的に溶媒を含まない、という特徴のうちの少なくとも1つを含む、請求項1から6のいずれか一項に記載の印刷方法。 - 前記樹脂組成物を加熱する段階、および/または、
前記樹脂組成物の少なくとも一部を照射している間および/または照射した後に、前記ポリマーを後硬化する段階、および/または、
前記ポリマーを洗浄する段階のうちの少なくとも1つをさらに含む、請求項1~7のいずれか一項に記載の印刷方法。 - 前記ポリマーを洗浄する段階をさらに含む、請求項1~8のいずれか一項に記載の印刷方法であって、前記洗浄する段階は、前記ポリマーを、アルカリ化合物、界面活性剤、および適切な溶媒を含む洗浄組成物と接触させることを含む、印刷方法。
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