JP5559151B2 - ナノ粒子を含む安定なポリイソシアネート - Google Patents
ナノ粒子を含む安定なポリイソシアネート Download PDFInfo
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/2805—Compounds having only one group containing active hydrogen
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
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- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen containing silicon
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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- C09C3/00—Treatment in general of inorganic materials, other than fibrous fillers, to enhance their pigmenting or filling properties
- C09C3/12—Treatment with organosilicon compounds
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- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
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Description
A)動的光散乱により測定して、200nm未満の平均粒径を有するナノ粒子を、
B)式(I):
R2は、Qが窒素である場合に存在し、水素、C1〜C12アルキル基若しくはC6〜C20アリール又はアラルキル基若しくはアスパラギン酸エステル基であり、
Qは、酸素、硫黄又は窒素であり、
Xは、加水分解性基であり、
Yは、同一又は異なって、アルキル基であり、
Zは、C1〜C12アルキレン基であり、
aは、1〜3の整数である。)
で示されるアルコキシシリル-及びNCO-含有付加物
と反応させ、次いで、生成物を
C)遊離NCO基を有するポリイソシアネート
とブレンドする、製造方法を提供する。
OrganosilicasolTM MEK-ST:メチルエチルケトンに分散されたコロイド状シリカ、粒径10〜15nm(製造業者の値)、SiO230質量%、H2O<0.5質量%、粘度<5mPas、Nissan Chemical America Corporation(米国)。
粒径は、HPPS 粒径アナライザー(Malvern、英国、Worcestershire)を用いて、動的光散乱により測定した。評価は、Dispersion Technologyソフトウエア4.10を用いて行った。多重散乱を防止するために、ナノ粒子の高度に希釈した分散体を調製した。1滴のナノ粒子分散体を、分散体の溶媒と同じ溶媒約2mlを含むセルに加え、振盪し、HPPSアナライザーにおいて、20〜25℃で測定した。評価に際して、分散媒の関係するパラメータ(温度、粘度及び屈折率)を考慮に入れた。有機溶媒の場合、ガラスセルを使用した。得られた結果は、強度/又は容積/粒径プロット、及び粒径についてのZ平均であった。多分散指数が0.5未満であるように注意した。
ジエチルN-(3-トリメトキシシリルプロピル)アスパルテートを、US-A 5 364 955 のExample 5 に従い、等モル量の3-アミノプロピルトリメトキシシランをマレイン酸ジエチルと反応させて、調製した。
標準的な攪拌装置に、室温で、546.1g(1当量)のヘキサメチレンジイソシアネートを加え、初期装填物上に、2L/時の速度で窒素を流した。次いで、453.9g(0.2当量)の実施例1aからのアルコキシシランを、室温で2時間かけて滴加した。温度は、理論NCO含量に達するまで、40℃に保持した。これにより、21.6%のNCO含量を有する透明淡黄色付加物を得た。
標準的な攪拌装置に、室温で、144.4gの実施例1bからの付加物を加え、初期装填物上に、2L/時の速度で窒素を流し、初期充填物を、還流下に72℃に加熱した。1155.6gの OrganosilicasolTM MEK-ST を30分かけて滴加し、温度は、72℃に8時間保持し、その後下げた。これにより、0.85%のNCO含量及び37.8%の固形分を有する半透明分散体を得た。
標準的な攪拌装置に、室温で、100gのメチルエチルケトン中の567.7g(1当量)の DesmodurTM N3300 を加え、初期装填物上に、2L/時の速度で窒素を流した。次いで、100gの酢酸ブチル中の232.3g(0.2当量)の実施例1からのアルコキシシランを、室温で3時間かけて滴加した。これにより、以下の特性を有する無色液体ポリイソシアネートを得た:
固形分:79質量%
NCO含量:9.6%
35.6gの実施例1dからのシラン官能性ポリイソシアネートを、93.75gの OrganosilicasolTM MEK-ST 及び20.65gの酢酸ブチルとブレンドした。これにより、2.25%のNCO含量、37.5%の固形分及び約50%固体/固体のSiO2含量を有するナノ粒子修飾ポリイソシアネートを得た。
234.4gのDesmodurTM N3300 を1265.8gの実施例1cからのオルガノゾルと混合し、回転蒸発器により、60℃、120mbarで、混合物の固形分を47.8%に調節した。これにより、約20mPas(23℃)の粘度、固体中約59%のSiO2及び4.05%のNCO含量を有する透明生成物を得た。
93.2gの実施例1dからのポリイソシアネートを、281.8gの実施例1cからのオルガノゾルと混合し、回転蒸発器により、60℃、120mbarで、混合物の固形分を54.8%に調節した。これにより、約50mPas(23℃)の粘度、固体中約50%のSiO2及び3.49%のNCO含量を有する透明生成物を得た。
ナノ粒子修飾ポリイソシアネートは、DE 10 2006 054289 に記載されているナノ粒子修飾ポリイソシアネートに相応して、非修飾ポリイソシアネートに比べ、硬さ及び/又は非引掻耐性の改良に適している。
Claims (11)
- 遊離NCO基を有するナノ粒子修飾ポリイソシアネートの製造方法であって、
A)動的光散乱により測定して、200nm未満の平均粒径を有するナノ粒子を、
B)式(I):
R2は、Qが窒素である場合に存在し、水素、C1〜C12アルキル基若しくはC6〜C20アリール又はアラルキル基若しくはアスパラギン酸エステル基であり、
Qは、酸素、硫黄又は窒素であり、
Xは、加水分解性基であり、
Yは、同一又は異なって、アルキル基であり、
Zは、C1〜C12アルキレン基であり、
aは、1〜3の整数である。)
で示されるアルコキシシリル-及びNCO-含有付加物
と反応させ、次いで、生成物を
C)遊離NCO基を有するポリイソシアネート
とブレンドする、製造方法。 - A)で使用する粒子は、有機溶媒中の分散体として使用される、請求項1に記載の製造方法。
- 溶媒は、酢酸ブチル、酢酸1-メトキシ-2-プロピル、酢酸エチル、トルエン、キシレン、ソルベントナフサ、メチルエチルケトン又はこれらの混合物である、請求項2に記載の製造方法。
- A)で使用する粒子は、酸化ケイ素、酸化アルミニウム、酸化セリウム、酸化ジルコニウム、酸化ニオブ又は酸化チタンである、請求項1〜3のいずれかに記載の製造方法。
- A)で使用する粒子は、分散体中で動的光散乱により測定したZ-平均で表して、5〜100nmの平均粒径を有する、請求項1〜4のいずれかに記載の製造方法。
- A)で使用する粒子は、表面修飾されている、請求項1〜5のいずれかに記載の製造方法。
- C)において、IPDI、MDI、TDI、HDI又はこれらの混合物に基づく上記種類のポリイソシアネートを使用する、請求項1〜7のいずれかに記載の製造方法。
- 請求項1〜8のいずれかに記載の製造方法により得られる、遊離NCO基を有するナノ粒子修飾ポリイソシアネート。
- 塗料、接着剤又はシーラントにおける、請求項9に記載の遊離NCO基を有するナノ粒子修飾ポリイソシアネートの使用。
- 請求項9に記載の遊離NCO基を有するナノ粒子修飾ポリイソシアネートを用いて得られる、被覆した又は接着結合した基材。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP20080009064 EP2119736A1 (de) | 2008-05-16 | 2008-05-16 | Stabile nanopartikelhaltige Polyisocyanate |
EP08009064.0 | 2008-05-16 | ||
PCT/EP2009/003192 WO2009138181A1 (de) | 2008-05-16 | 2009-05-05 | Stabile nanopartikelhaltige polyisocyanate |
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JP2011521026A JP2011521026A (ja) | 2011-07-21 |
JP2011521026A5 JP2011521026A5 (ja) | 2012-06-14 |
JP5559151B2 true JP5559151B2 (ja) | 2014-07-23 |
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JP2011508821A Expired - Fee Related JP5559151B2 (ja) | 2008-05-16 | 2009-05-05 | ナノ粒子を含む安定なポリイソシアネート |
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Country | Link |
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US (1) | US8669323B2 (ja) |
EP (2) | EP2119736A1 (ja) |
JP (1) | JP5559151B2 (ja) |
CN (1) | CN102027032B (ja) |
AT (1) | ATE544798T1 (ja) |
ES (1) | ES2380517T3 (ja) |
TW (1) | TW201008964A (ja) |
WO (1) | WO2009138181A1 (ja) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
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US9202688B2 (en) | 2010-04-23 | 2015-12-01 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US9359689B2 (en) | 2011-10-26 | 2016-06-07 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US10753012B2 (en) | 2010-10-27 | 2020-08-25 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
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CN111662573B (zh) * | 2020-06-20 | 2021-10-22 | 万华化学集团股份有限公司 | 一种植物油与有机硅复合改性、可uv固化的纳米二氧化硅、制备方法及其应用 |
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JP2002363438A (ja) * | 2001-06-04 | 2002-12-18 | Wakayama Prefecture | 無機補強充填剤及びこれを含有した熱可塑性樹脂組成物 |
EP1448724B1 (de) | 2001-11-23 | 2007-01-31 | DEUTSCHE AMPHIBOLIN-WERKE VON ROBERT MURJAHN GmbH + Co. KG | Beschichtungsmasse enthaltend nanopartikel, verwendung der beschichtungsmasse und verfahren zur herstellung von beschichtungen |
DE10247359A1 (de) | 2002-10-10 | 2004-04-29 | Basf Coatings Ag | Nanopartikel, Verfahren zur Modifizierung ihrer Oberfläche, Dispersion der Nanopartikel, Verfahren zu ihrer Herstellung und ihre Verwendung |
JP2005298365A (ja) * | 2004-04-07 | 2005-10-27 | Mitsui Takeda Chemicals Inc | 有機ポリイソシアネート組成物 |
CN1594388A (zh) * | 2004-06-22 | 2005-03-16 | 上海高分子材料研究开发中心 | 一种纳米阴离子型聚氨酯复合水乳胶的制备方法 |
DK1773919T3 (da) | 2004-07-16 | 2009-02-16 | Alberdingk Boley Gmbh | Vandig bindemiddeldispersion med nanopartikler, fremgangsmåde til fremstilling af denne og anvendelse heraf |
DE102004040264A1 (de) | 2004-08-19 | 2006-02-23 | Consortium für elektrochemische Industrie GmbH | Partikel mit geschützten Isocyanatgruppen |
DE102004050747A1 (de) * | 2004-10-19 | 2006-04-27 | Basf Coatings Ag | Beschichtungsmittel enthaltend Addukte mit Alkoxysilanfunktionalität |
CN1272355C (zh) * | 2005-02-05 | 2006-08-30 | 南京工业大学 | 聚氨酯材料的制备方法 |
KR20070104460A (ko) * | 2005-02-10 | 2007-10-25 | 와커 헤미 아게 | 보호된 이소시아네이트기를 가지는 입자를 함유하는 래커 |
DE102005034347A1 (de) * | 2005-07-22 | 2007-01-25 | Consortium für elektrochemische Industrie GmbH | Lacke enthaltend Partikel |
DE102005034348A1 (de) | 2005-07-22 | 2007-01-25 | Consortium für elektrochemische Industrie GmbH | Lacke enthaltend Partikel |
DE102006054289A1 (de) | 2006-11-17 | 2008-05-21 | Bayer Materialscience Ag | Nanopartikelmodifizierte Polyisocyanate |
-
2008
- 2008-05-16 EP EP20080009064 patent/EP2119736A1/de not_active Withdrawn
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2009
- 2009-05-05 AT AT09745515T patent/ATE544798T1/de active
- 2009-05-05 ES ES09745515T patent/ES2380517T3/es active Active
- 2009-05-05 CN CN2009801177839A patent/CN102027032B/zh not_active Expired - Fee Related
- 2009-05-05 US US12/993,023 patent/US8669323B2/en not_active Expired - Fee Related
- 2009-05-05 EP EP09745515A patent/EP2283055B1/de not_active Not-in-force
- 2009-05-05 JP JP2011508821A patent/JP5559151B2/ja not_active Expired - Fee Related
- 2009-05-05 WO PCT/EP2009/003192 patent/WO2009138181A1/de active Application Filing
- 2009-05-15 TW TW98116084A patent/TW201008964A/zh unknown
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9202688B2 (en) | 2010-04-23 | 2015-12-01 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US9328432B2 (en) | 2010-04-23 | 2016-05-03 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US9617657B2 (en) | 2010-04-23 | 2017-04-11 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US9856581B2 (en) | 2010-04-23 | 2018-01-02 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US10753012B2 (en) | 2010-10-27 | 2020-08-25 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
US9359689B2 (en) | 2011-10-26 | 2016-06-07 | Pixelligent Technologies, Llc | Synthesis, capping and dispersion of nanocrystals |
Also Published As
Publication number | Publication date |
---|---|
TW201008964A (en) | 2010-03-01 |
CN102027032A (zh) | 2011-04-20 |
US20110100259A1 (en) | 2011-05-05 |
CN102027032B (zh) | 2013-03-27 |
WO2009138181A1 (de) | 2009-11-19 |
JP2011521026A (ja) | 2011-07-21 |
EP2119736A1 (de) | 2009-11-18 |
ATE544798T1 (de) | 2012-02-15 |
ES2380517T3 (es) | 2012-05-14 |
US8669323B2 (en) | 2014-03-11 |
EP2283055B1 (de) | 2012-02-08 |
EP2283055A1 (de) | 2011-02-16 |
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