JP2017527455A - 3dプリント用のゲル化剤を含むインク - Google Patents
3dプリント用のゲル化剤を含むインク Download PDFInfo
- Publication number
- JP2017527455A JP2017527455A JP2016571092A JP2016571092A JP2017527455A JP 2017527455 A JP2017527455 A JP 2017527455A JP 2016571092 A JP2016571092 A JP 2016571092A JP 2016571092 A JP2016571092 A JP 2016571092A JP 2017527455 A JP2017527455 A JP 2017527455A
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- JP
- Japan
- Prior art keywords
- ink
- cases
- gelling agent
- compound
- acrylate
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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- 239000003349 gelling agent Substances 0.000 title claims abstract description 112
- 238000010146 3D printing Methods 0.000 title description 11
- 238000000034 method Methods 0.000 claims abstract description 57
- 239000000463 material Substances 0.000 claims abstract description 50
- 239000000758 substrate Substances 0.000 claims abstract description 26
- 230000007704 transition Effects 0.000 claims abstract description 24
- 238000007639 printing Methods 0.000 claims abstract description 20
- 238000001879 gelation Methods 0.000 claims abstract description 9
- 150000001875 compounds Chemical class 0.000 claims description 68
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 44
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 125000004432 carbon atom Chemical group C* 0.000 claims description 33
- 230000002209 hydrophobic effect Effects 0.000 claims description 32
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- 239000013626 chemical specie Substances 0.000 claims description 25
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000004202 carbamide Substances 0.000 claims description 18
- 150000001408 amides Chemical group 0.000 claims description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 16
- 125000003118 aryl group Chemical group 0.000 claims description 14
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 10
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 9
- 230000005540 biological transmission Effects 0.000 claims description 6
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- 239000000976 ink Substances 0.000 description 296
- 239000000499 gel Substances 0.000 description 56
- 241000894007 species Species 0.000 description 42
- -1 acrylate amine Chemical class 0.000 description 36
- 239000000203 mixture Substances 0.000 description 31
- 238000000151 deposition Methods 0.000 description 23
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- 229930195733 hydrocarbon Natural products 0.000 description 7
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- LAQYHRQFABOIFD-UHFFFAOYSA-N 2-methoxyhydroquinone Chemical compound COC1=CC(O)=CC=C1O LAQYHRQFABOIFD-UHFFFAOYSA-N 0.000 description 4
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- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
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- 238000011960 computer-aided design Methods 0.000 description 4
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- 230000005855 radiation Effects 0.000 description 4
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 3
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- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 2
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 2
- YIDSTEJLDQMWBR-UHFFFAOYSA-N 1-isocyanatododecane Chemical compound CCCCCCCCCCCCN=C=O YIDSTEJLDQMWBR-UHFFFAOYSA-N 0.000 description 2
- XIFGNGCAPGVNJX-UHFFFAOYSA-N 1-isocyanatoheptadecane Chemical compound CCCCCCCCCCCCCCCCCN=C=O XIFGNGCAPGVNJX-UHFFFAOYSA-N 0.000 description 2
- GFLXBRUGMACJLQ-UHFFFAOYSA-N 1-isocyanatohexadecane Chemical compound CCCCCCCCCCCCCCCCN=C=O GFLXBRUGMACJLQ-UHFFFAOYSA-N 0.000 description 2
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- YIKSHDNOAYSSPX-UHFFFAOYSA-N 1-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C=CC=C2C(C)C YIKSHDNOAYSSPX-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
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- UHFFVFAKEGKNAQ-UHFFFAOYSA-N 2-benzyl-2-(dimethylamino)-1-(4-morpholin-4-ylphenyl)butan-1-one Chemical compound C=1C=C(N2CCOCC2)C=CC=1C(=O)C(CC)(N(C)C)CC1=CC=CC=C1 UHFFVFAKEGKNAQ-UHFFFAOYSA-N 0.000 description 2
- ZCDADJXRUCOCJE-UHFFFAOYSA-N 2-chlorothioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3SC2=C1 ZCDADJXRUCOCJE-UHFFFAOYSA-N 0.000 description 2
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- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 2
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- 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
- 238000003786 synthesis reaction Methods 0.000 description 1
- MUTNCGKQJGXKEM-UHFFFAOYSA-N tamibarotene Chemical compound C=1C=C2C(C)(C)CCC(C)(C)C2=CC=1NC(=O)C1=CC=C(C(O)=O)C=C1 MUTNCGKQJGXKEM-UHFFFAOYSA-N 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- ABVVEAHYODGCLZ-UHFFFAOYSA-N tridecan-1-amine Chemical compound CCCCCCCCCCCCCN ABVVEAHYODGCLZ-UHFFFAOYSA-N 0.000 description 1
- KEROTHRUZYBWCY-UHFFFAOYSA-N tridecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCCOC(=O)C(C)=C KEROTHRUZYBWCY-UHFFFAOYSA-N 0.000 description 1
- 229940087291 tridecyl alcohol Drugs 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 1
- 229940057402 undecyl alcohol Drugs 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 150000003673 urethanes Chemical class 0.000 description 1
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Abstract
Description
1つの態様において、3Dプリンタに使用するためのインクがここに記載されている。いくつかの実施の形態において、ここに記載されたインクは、硬化性材料およびゲル化剤を含む。ここに記載されたインクのゲル化剤は、ある場合には、エチレン不飽和種などの硬化性種を含む。そのゲル化剤は、1つ以上のウレタン、尿素、および/またはアミド部分などの、水素結合に関与できる窒素含有部分を1つ以上含んでもよい。その上、いくつかの実施の形態において、ここに記載されたインクのゲル化剤は、1つ以上の疎水性セグメントを有する化学種を含み得る。例えば、ある場合には、ゲル化剤は、1つ以上のウレタン部分により疎水性セグメントに結合した1つ以上の末端オレフィン部分を有する化学種を含む。そのような場合のあるものにおいて、その1つ以上のウレタン部分は、疎水性セグメントを1つ以上のウレタン部分に直接結合する。他の場合には、1つ以上のウレタン部分は、その疎水性セグメントを1つ以上の末端オレフィン部分に間接的に結合する。いくつかの実施の形態において、例えば、そのゲル化剤の化学種は、前記1つ以上のウレタン部分と前記1つ以上の末端オレフィン部分との間に配置された1つ以上の追加の疎水性セグメントをさらに含む。さらに、いくつかの実施の形態において、その化学種は二量体である。
は、R2部分間の1つの炭素−炭素結合を表す。
別の態様において、3D物品または物体をプリントする方法がここに記載されている。いくつかの実施の形態において、3D物品をプリントする方法は、流体状態にあるここに記載されたインクの層を基体上に選択的に堆積させる工程を有してなる。先の項目Iに記載されたいかなるインクを使用してもよい。例えば、ある場合には、そのインクは、硬化性材料およびゲル化剤を含み、そのゲル化剤は、1つ以上のウレタン部分により疎水性セグメントに結合した1つ以上の末端オレフィン部分を有する化学種を含む。さらに、インクの層は、コンピュータ可読フォーマットにある3D物品の画像にしたがって堆積させることができる。いくつかの実施の形態において、インクは、事前に選択されたコンピュータ支援設計(CAD)パラメータにしたがって堆積される。
別の態様において、プリントされた3D物品がここに記載されている。いくつかの実施の形態において、プリントされた3D物品は、ここに記載されたインクから形成される。項目Iまたは項目IIにおいて先に記載されたどのインクを使用してもよい。例えば、ある場合には、インクは、硬化性材料およびゲル化剤を含み、ここで、ゲル化剤は、1つ以上のウレタン部分により疎水性セグメントに結合した1つ以上の末端オレフィン部分を有する化学種を含む。
ゲル化剤
ここに記載された1つの実施の形態によるインクのゲル化剤を以下のように調製した。このゲル化剤をゲル化剤1と表示する。最初に、62.3g(0.371モル)のヘキサメチレンジイソシアネート(ウィスコンシン州、ミルウォーキー所在のSigma−Aldrich Chemical Co.)、100.0g(0.186モル)のダイマージオール(PRIPOL 2033、デラウェア州、ニューカッスル所在のUniqema)、および43.0g(0.371モル)の1,4−ブタンジオールビニルエーテル(Sigma−Aldrich)を、磁気撹拌子を備えた400mLのビーカーに入れた。このビーカーを、撹拌ホットプレート上の110℃のシリコーン油浴内に置き、撹拌を始めた。このビーカーに3滴の触媒(Fascat 4202、ジラウリン酸ジブチルスズ、ペンシルベニア州、フィラデルフィア所在のElf Atochem North America,Inc.)を加え、この混合物を110℃で約2時間に亘り反応させた。フーリエ変換赤外分光法(FT−IR)による反応生成物の分析は、出発材料のNCO官能基の全てが消費されたことを示した。詳しくは、FT−IRは、約2285cm-1でのピーク(イソシアネート部分に対応する)の不在(または消失)並びに約1740〜1680cm-1および約1540〜1530cm-1のピーク(ウレタン部分に対応する)の出現(または大きさの増加)を示した。次いで、最終的なウレタン含有生成物をアルミニウム製平鍋に注ぎ、冷ました。この生成物は、先の式(II)の構造を有する化学種を含んでいた。
ゲル化剤
ここに記載された1つの実施の形態によるインクのゲル化剤を以下のように調製した。このゲル化剤をゲル化剤2と表示する。最初に、50.0g(0.167モル)のオクタデシルイソシアネート(Mondur O、ペンシルベニア州、ピッツバーグ所在のBayer Corp.)、および19.6g(0.169モル)の1,4−ブタンジオールビニルエーテル(Sigma−Aldrich)を、磁気撹拌子を備えた200mLのビーカーに入れた。次いで、このビーカーを、撹拌ホットプレート上の110℃のシリコーン油浴内に置き、撹拌を始めた。2滴の触媒(Fascat 4202、ジラウリン酸ジブチルスズ、Elf Atochem)を加え、この混合物を110℃で約2時間に亘り反応させた。反応生成物のFT−IR分析は、実施例1に記載されたように、NCO官能基の全てが消費されたことを示した。次いで、最終的なウレタン含有生成物をアルミニウム製平鍋に注ぎ、冷ました。この最終生成物は、約135℃でFerranti−Shirleyコーンプレート粘度計により測定して、約2.63cPの粘度により特徴付けられた。この生成物は、式(VIII):
ゲル化剤
ここに記載されたいくつかの実施の形態による追加のゲル化剤を以下のように調製した。これらのゲル化剤をゲル化剤3〜27と表示する。
インク
ここに記載されたいくつかの実施の形態によるインクを以下のように調製した。詳しくは、様々なタイプのインクを調製するために、表IIIの成分を反応槽内で混合した。表IIIの量は、インクの総質量に基づく、インクの各成分の質量%を称する。各インクについて、適切な混合物を、撹拌しながら、約75〜85℃の温度に加熱した。加熱と撹拌は、混合物が実質的に均質な溶解状態に達するまで続けた。次いで、溶解した混合物を濾過した。次に、濾過した混合物を周囲温度まで冷ませた。
インク
ここに記載されたいくつかの実施の形態による追加のインクを、実施例1のゲル化剤1を、下記の表Vに示された量の実施例3からのいくつかのゲル化剤で置き換えたことを除いて、インク1について実施例4において先に記載したのと同じ様式で調製した。表Vの質量パーセントは、インクの総質量に基づくゲル化剤の質量パーセントである。その上、下記の表VIは、表Vに列挙されたインクのいくつかに関するゲル化時間およびゲル化開始温度を与えている。ゲル化時間は、項目IIにおいて先に記載したように決定した。ゲル化開始温度は、毎分1℃で80〜90℃からインクを冷却し、粘度において大きい変化または「段階」が始まった粘度対温度曲線における最初の地点に基づいて、ゲル化が始まった温度を書き留めることにより、決定した。ここで、粘度は、先の実施例4に概して記載されたように測定した。
Claims (19)
- 三次元物品をプリントする方法において、
温度T1のインクを温度T2の基体上に噴射して、該基体上に該インクの層を形成する工程、および
前記インクの層を硬化させる工程、
を有してなり、
T1はT2より高く、
未硬化状態の前記インクは、T1より低く、T2より高い液体−ゲル転移温度を有し、
前記インクは硬化性材料およびゲル化剤を含み、該ゲル化剤は、1つ以上のウレタン、尿素、および/またはアミド部分により疎水性セグメントに結合した1つ以上の末端オレフィン部分を有する化学種を含み、
前記インクの層は、T2で未硬化状態にある前記インクの逆数分で表されたゲル化速度R2の約60%以内である、mg/s/in2で表された速度R1で前記基体上に堆積され、この百分率が、R1およびR2の大きい方に基づくものである、方法。 - R1およびR2の間の差が、R1およびR2の大きい方の20〜60%である、請求項1記載の方法。
- R1およびR2の間の差が、R1およびR2の大きい方の30〜50%である、請求項1記載の方法。
- T2で未硬化状態にある前記インクのゲル化時間GTが15分と30分の間である、請求項1記載の方法。
- T2で未硬化状態にある前記インクのゲル化時間GTが31分と45分の間である、請求項1記載の方法。
- T1が70〜90℃であり、T2が20〜30℃である、請求項1記載の方法。
- T2が45〜45℃である、請求項1記載の方法。
- 前記硬化性材料が、ウレタン(メタ)アクリレートを含む1種類以上のオリゴマー材料を含む、請求項1記載の方法。
- 前記硬化性材料が、前記インク中に、該インクの総質量に基づいて約50〜98質量%の量で存在し、前記ゲル化剤が、前記インク中に、該インクの総質量に基づいて約2〜20質量%の量で存在する、請求項1記載の方法。
- 前記インクが、約30℃と約75℃の間の液体−ゲル転移を示す、請求項1記載の方法。
- 前記インクが、約0.03から5mmの厚さのときに、約350nmと約750nmの間で、少なくとも約90%の透過率の光透過性を有する、請求項1記載の方法。
- 前記インクの複数の層が、コンピュータ可読フォーマットにある前記三次元物品の画像にしたがって前記基体上に堆積される、請求項1記載の方法。
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WO2019021292A1 (en) | 2017-07-28 | 2019-01-31 | Stratasys Ltd. | METHOD AND SYSTEM FOR MANUFACTURING AN OBJECT HAVING PROPERTIES OF A BLOOD VESSEL |
DK3658990T3 (da) * | 2017-07-28 | 2024-01-29 | Stratasys Ltd | Formuleringer, som kan anvendes i additiv fremstilling af et tredimensionelt objekt af et blødt materiale |
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JP2012232578A (ja) * | 2011-05-03 | 2012-11-29 | Xerox Corp | 三次元オブジェクトを製造する方法 |
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CN106661357A (zh) | 2017-05-10 |
US9732241B2 (en) | 2017-08-15 |
CN106661357B (zh) | 2020-07-28 |
EP3152266B1 (en) | 2020-10-07 |
US20170298244A1 (en) | 2017-10-19 |
US20150353750A1 (en) | 2015-12-10 |
EP3540017B1 (en) | 2021-10-27 |
EP3540017A1 (en) | 2019-09-18 |
JP2018202869A (ja) | 2018-12-27 |
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EP3152266A1 (en) | 2017-04-12 |
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