JP2020512477A - 照射硬化性樹脂の組成と獲得方法 - Google Patents
照射硬化性樹脂の組成と獲得方法 Download PDFInfo
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Abstract
Description
本発明は、少なくとも一種のエポキシアクリル樹脂、ポリメチルメタクリレート、グラフェン、ハロイサイトナノチューブと、一つまたは複数の光開始剤で組成され、主にステレオリソグラフィーで得られる立体製品に使用される新規照射硬化性樹脂及びその新規獲得方法に関する。
3Dプリントまたはステレオリソグラフィーで複雑な立体製品の作成方法は以前から知られ、下記の特許文献に記載されている通り(レーザー、DLPまたはLCDで硬化する)照射硬化性液の使用には様々な条件を必要とする。
・二官能以上の官能を有する液状エポキシ樹脂または二官能以上の官能を有するエポキシ樹脂で組成される混合液が40〜80重量%
・陽イオン性光開始剤または陽イオン性光開始混合剤が0.1〜10重量%
・遊離基性光開始剤または遊離基性光開始混合剤が0.1〜10重量%
・特定水酸化合物が5〜40重量%
・二官能以上の(メタ)アクリレート官能を有している少なくとも一種の液状ポリ(メタ)アクリレートが0〜15重量%
・全(メタ)アクリレートの50重量%以下の(E)成分を含む、少なくとも一種の芳香族
・脂環式液状ジアクリレートが5〜40重量%
・二官能以上の官能を有する液状エポキシ樹脂または二官能以上の官能を有するエポキシ樹脂で組成される混合液が40〜80重量%
・陽イオン性光開始剤または陽イオン性光開始混合剤が0.1〜10重量%の遊離基性光開始剤または遊離基性光開始混合剤が0.1〜10重量%
・一種の水酸化合物が2〜40重量%
・少なくとも(メタ)アクリレート官能を二官能以上有する、少なくとも一種の液状(メタ)アクリレートを含む遊離基によるポリマー性液体成分が2〜40重量%
・一種以上のヂ(メタ)アクリレートを5〜40重量%で好む
(A)ポリマー格子を構成する開環反応を可能にさせる少なくとも二基を有する多官能性液体組成物が40〜80重量%
(B)陽イオン性光開始剤または陽イオン性光開始混合剤が0.1〜10重量%
(C)分子には少なくとも一種の不飽和基と一種の水酸基を含む化合物が2〜30重量%の
(D)不飽和基を含まない水酸化合物が0〜30重量%
(E)二官能以上で水酸基を含まない少なくとも一種の液状ポリ(メタ)アクリレートが0〜30重量%
(F)水酸基を含まない少なくとも一種の芳香族、脂環式液状ジ(メタ)アクリレートが0〜40重量%
(G)反応性希釈剤が0〜40重量%で、(A),(B),(C),(D),(E),(F)及び(G)の合計成分が100重量%で、(C),(D),(E),(F)および(G)成分はそれぞれ異なり、組成物には遊離基性開始剤は全く無い。
照射硬化性樹脂の好まれる組成は以下のように実施する。
(A)二官能以上のエポキシ官能を有する少なくとも一種の液状エポキシ樹脂を40〜60重量%
(B)(メタ)アクリレート官能を有している少なくとも一種の液状ポリ(メタ)アクリレートを0.1〜40重量%で、(B)は(メタ)アクリレートの全重量の50%を限度とする。
(C)少なくとも一種の組成用陽イオン性光開始剤を0.1〜10重量%
(D)少なくとも一種の組成用基性光開始剤を0.1〜10重量%
(E)少なくとも一種のOH末端基を含んだポリエーテル、ポリエステル又はポリウレタンを5〜15重量%
(F)分子に少なくとも一種の不飽和基と一種の水酸基を含む化合物を2〜30重量%
(G)不飽和基を含まない水酸化合物を0〜30重量%
(H)酸化グラフェンまたは接着成分で官能化したグラフェンを0.1〜5重量%
(I)ハロイサイトナノチューブなど強化物質を0.1〜20重量%を含む。
化合物の合計は100重量%となる。
i)重合体の混合
ii)ナノ素子で強化
iii)立体製品を得るための3Dプリント
Claims (14)
- 以下のa)〜i)の項目を備えることを特徴とする、3Dプリントに適合した照射硬化性樹脂の組成物。
a)重合格子を形成する開環機構と反応できる少なくとも2基を有する少なくとも1種の液状エポキシ樹脂を40〜60重量%
b)(メタ)アクリレート官能を有し、(メタ)アクリレートの全重量の50%を限度とする少なくとも一種の液状ポリ(メタ)アクリレートを0.1〜40重量%
c)少なくとも一種の組成用陽イオン性光開始剤を0.1〜10重量%
d)少なくとも一種の遊離基による光開始剤を0.1〜10重量%
e)少なくとも一種のOH末端基を含んだポリエーテルを5〜15重量%。
f)分子に少なくとも一種の不飽和基と一種の水酸基を含む化合物を2〜30重量%
g)不飽和基を含まない水酸化合物を0〜30重量%
h)グラフェンを0.1〜5%
i)ハロイサイトナノチューブを0.1〜20% - 少なくとも一種の液状エポキシ樹脂は2官能性であることを特徴とする、請求項1に記載の照射硬化性樹脂の組成物。
- 少なくとも2官能の少なくとも一種の液状エポキシ樹脂を特徴とする、請求項1又は2に記載の照射硬化性樹脂の組成物。
- OH末端基を含んだ少なくとも一種のポリエステルを特徴とする、請求項1乃至3のいずれかに記載の照射硬化性樹脂の組成物。
- OH末端基を含んだ少なくとも一種のポリエステルの5〜15重量%を特徴とする、請求項1乃至4のいずれかに記載の照射硬化性樹脂の組成物。
- OH末端基を含んだ少なくとも一種のポリウレタンを特徴とする、請求項1乃至5のいずれかに記載の照射硬化性樹脂の組成物。
- OH末端基を含んだ少なくとも一種のポリウレタンの5〜15重量%を特徴とする、請求項1乃至6のいずれかに記載の照射硬化性樹脂の組成物。
- ポリエーテル、ポリエステル、ポリウレタンの総合割合が5%〜15重量%であることを特徴とする、請求項5又は7に記載の照射硬化性樹脂の組成物。
- グラフェンを基材に接着する接着剤を特徴とする、請求項1乃至8のいずれかに記載の照射硬化性樹脂の組成物。
- グラフェンが酸化グラフェンであることを特徴とする、請求項1乃至9のいずれかに記載の照射硬化性樹脂の組成物。
- グラフェンが官能グラフェンであることを特徴とする、請求項1乃至9のいずれかに記載の照射硬化性樹脂の組成物。
- 以下のa)〜e)の段階を備えることを特徴とする、請求項1乃至11のいずれかに記載の照射硬化性樹脂の獲得方法。
a)以下の成分の混合。
液状エポキシ樹脂、液状ポリ(メタ)アクリレート、陽イオン性光開始剤、遊離基性光開始剤、分子に少なくとも一種の不飽和基と少なくとも一種の水酸基を含む化合物、不飽和基を全く持たない水酸化合物、ポリエーテルとポリエステルかポリウレタン何れかの成分。
混合剤に磁石チップを追加し、磁気撹拌機で撹拌する。
b)a)で得た混合剤を無菌で不透明の容器に移す。
c)無菌で不透明の容器に入っている混合剤にグラフェンとハロイサイトナノチューブを加える。
d)容器は無菌で不透明の蓋で閉める。
e)c)の段階で得た混合剤を液中超音波撹拌で予備重合から照射硬化性の組成物を得る。 - 磁気撹拌機で200〜800rpmで3日間撹拌することを特徴とする、請求項12に記載の照射硬化性樹脂の獲得方法。
- 超音波の周波数が25〜45kHzで、液体の温度は常温で、撹拌時間は3〜6時間で、その際に平均温度が35度から60度に上昇することを特徴とする、請求項12又は13に記載の照射硬化性樹脂の獲得方法。
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Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06228413A (ja) * | 1992-12-21 | 1994-08-16 | Ciba Geigy Ag | 感光性組成物 |
JP2004217934A (ja) * | 2003-01-13 | 2004-08-05 | Three D Syst Inc | オキセタン化合物を含有するステレオリソグラフィー用樹脂 |
JP2006028522A (ja) * | 1995-05-12 | 2006-02-02 | Asahi Denka Kogyo Kk | 光学的立体造形用樹脂組成物および光学的立体造形法 |
JP2007516318A (ja) * | 2003-11-06 | 2007-06-21 | ハンツマン・アドヴァンスト・マテリアルズ・(スイッツランド)・ゲーエムベーハー | 高い透明性と改良された機械的性質とを有する硬化物品を製造するための光硬化性組成物 |
WO2013172407A1 (ja) * | 2012-05-18 | 2013-11-21 | シーメット株式会社 | 光学的立体造形用樹脂組成物 |
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Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3708296A (en) | 1968-08-20 | 1973-01-02 | American Can Co | Photopolymerization of epoxy monomers |
US4339567A (en) | 1980-03-07 | 1982-07-13 | Ciba-Geigy Corporation | Photopolymerization by means of sulphoxonium salts |
US4383025A (en) | 1980-07-10 | 1983-05-10 | Ciba-Geigy Corporation | Photopolymerization by means of sulfoxonium salts |
US4398014A (en) | 1980-11-04 | 1983-08-09 | Ciba-Geigy Corporation | Sulfoxonium salts and their use as polymerization catalysts |
ATE37242T1 (de) | 1984-02-10 | 1988-09-15 | Ciba Geigy Ag | Verfahren zur herstellung einer schutzschicht oder einer reliefabbildung. |
GB8414525D0 (en) | 1984-06-07 | 1984-07-11 | Ciba Geigy Ag | Sulphoxonium salts |
EP0360869B1 (en) | 1988-02-19 | 1998-01-07 | Asahi Denka Kogyo Kabushiki Kaisha | Resin composition for optical modeling |
JPH07103218B2 (ja) | 1988-09-13 | 1995-11-08 | 旭電化工業株式会社 | 光学的造形用樹脂組成物 |
ES2147777T3 (es) | 1993-09-16 | 2000-10-01 | Ciba Sc Holding Ag | Compuestos vinileter con grupos funcionales adicionales, distintos de vinileter, y su utilizacion en la formulacion de compuestos reticulables. |
EP0822445B2 (de) | 1996-07-29 | 2005-02-09 | Huntsman Advanced Materials (Switzerland) GmbH | Flüssige, strahlungshärtbare Zusammensetzung, insbesondere für die Stereolithographie |
US6136497A (en) * | 1998-03-30 | 2000-10-24 | Vantico, Inc. | Liquid, radiation-curable composition, especially for producing flexible cured articles by stereolithography |
ES2345031T3 (es) * | 2000-02-08 | 2010-09-14 | Huntsman Advanced Materials (Switzerland) Gmbh | Composicion liquida curable por radiacion, especialmente para estereolitografia. |
US6989225B2 (en) * | 2002-07-18 | 2006-01-24 | 3D Systems, Inc. | Stereolithographic resins with high temperature and high impact resistance |
TWI406086B (zh) * | 2004-03-22 | 2013-08-21 | 3D Systems Inc | 可光硬化組合物 |
US20120296012A1 (en) * | 2010-02-04 | 2012-11-22 | Drexel University | Room temperature ionic liquid-epoxy systems as dispersants and matrix materials for nanocomposites |
CN103819656B (zh) * | 2014-02-18 | 2017-06-23 | 青岛科技大学 | 一种氧化石墨烯/光固化树脂复合材料及其制备方法和应用 |
-
2017
- 2017-03-31 ES ES201700369A patent/ES2685280B2/es not_active Expired - Fee Related
-
2018
- 2018-04-02 EP EP18775975.8A patent/EP3604375A4/en not_active Withdrawn
- 2018-04-02 US US16/499,414 patent/US11385541B2/en active Active
- 2018-04-02 RU RU2019134903A patent/RU2019134903A/ru unknown
- 2018-04-02 AU AU2018242233A patent/AU2018242233A1/en not_active Abandoned
- 2018-04-02 JP JP2020503367A patent/JP2020512477A/ja active Pending
- 2018-04-02 MX MX2019011654A patent/MX2019011654A/es unknown
- 2018-04-02 BR BR112019020296-0A patent/BR112019020296A2/pt not_active Application Discontinuation
- 2018-04-02 CN CN201880031566.7A patent/CN110650986A/zh active Pending
- 2018-04-02 KR KR1020197032138A patent/KR20190128086A/ko not_active Application Discontinuation
- 2018-04-02 CA CA3058543A patent/CA3058543A1/en not_active Abandoned
- 2018-04-02 WO PCT/ES2018/000039 patent/WO2018178423A2/es active Application Filing
-
2019
- 2019-10-29 ZA ZA2019/07156A patent/ZA201907156B/en unknown
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH06228413A (ja) * | 1992-12-21 | 1994-08-16 | Ciba Geigy Ag | 感光性組成物 |
JP2006028522A (ja) * | 1995-05-12 | 2006-02-02 | Asahi Denka Kogyo Kk | 光学的立体造形用樹脂組成物および光学的立体造形法 |
JP2004217934A (ja) * | 2003-01-13 | 2004-08-05 | Three D Syst Inc | オキセタン化合物を含有するステレオリソグラフィー用樹脂 |
JP2007516318A (ja) * | 2003-11-06 | 2007-06-21 | ハンツマン・アドヴァンスト・マテリアルズ・(スイッツランド)・ゲーエムベーハー | 高い透明性と改良された機械的性質とを有する硬化物品を製造するための光硬化性組成物 |
WO2013172407A1 (ja) * | 2012-05-18 | 2013-11-21 | シーメット株式会社 | 光学的立体造形用樹脂組成物 |
Non-Patent Citations (1)
Title |
---|
RASHEED ATIF, ET AL.: "Fractography analysis of 0.5 wt%multi-layer graphene/nanoclay reinforced epoxy nanocomposites", AIMS MATERIALS SCIENCE, vol. Volume 3, Issue 3, JPN6022010907, 2016, pages 1266 - 1280, ISSN: 0004907649 * |
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AU2018242233A1 (en) | 2019-11-07 |
WO2018178423A3 (es) | 2018-11-22 |
EP3604375A4 (en) | 2020-12-02 |
ES2685280B2 (es) | 2019-06-21 |
US11385541B2 (en) | 2022-07-12 |
RU2019134903A3 (ja) | 2021-07-14 |
KR20190128086A (ko) | 2019-11-14 |
ZA201907156B (en) | 2021-08-25 |
EP3604375A2 (en) | 2020-02-05 |
ES2685280A1 (es) | 2018-10-08 |
CN110650986A (zh) | 2020-01-03 |
MX2019011654A (es) | 2020-07-14 |
US20200026185A1 (en) | 2020-01-23 |
CA3058543A1 (en) | 2018-10-04 |
BR112019020296A2 (pt) | 2020-06-16 |
RU2019134903A (ru) | 2021-04-30 |
WO2018178423A2 (es) | 2018-10-04 |
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