JP5586589B2 - ポリカーボネートポリオールに基づくポリウレタン−ポリウレア分散体 - Google Patents
ポリカーボネートポリオールに基づくポリウレタン−ポリウレア分散体 Download PDFInfo
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- JP5586589B2 JP5586589B2 JP2011511632A JP2011511632A JP5586589B2 JP 5586589 B2 JP5586589 B2 JP 5586589B2 JP 2011511632 A JP2011511632 A JP 2011511632A JP 2011511632 A JP2011511632 A JP 2011511632A JP 5586589 B2 JP5586589 B2 JP 5586589B2
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- 150000003077 polyols Chemical class 0.000 title claims description 12
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- 125000003118 aryl group Chemical group 0.000 description 3
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- 229910052751 metal Inorganic materials 0.000 description 3
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- 150000003141 primary amines Chemical class 0.000 description 3
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- 150000003512 tertiary amines Chemical class 0.000 description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 2
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- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
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- CDBAMNGURPMUTG-UHFFFAOYSA-N 4-[2-(4-hydroxycyclohexyl)propan-2-yl]cyclohexan-1-ol Chemical compound C1CC(O)CCC1C(C)(C)C1CCC(O)CC1 CDBAMNGURPMUTG-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
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- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/2815—Monohydroxy compounds
- C08G18/283—Compounds containing ether groups, e.g. oxyalkylated monohydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/44—Polycarbonates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/722—Combination of two or more aliphatic and/or cycloaliphatic polyisocyanates
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
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Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
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- Medicinal Chemistry (AREA)
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- Manufacturing & Machinery (AREA)
- Dispersion Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyurethanes Or Polyureas (AREA)
- Paints Or Removers (AREA)
Description
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、および
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を含み、該分散体は、前記合成成分の合計重量を基準として60重量%〜90重量%の成分I.2)を含有し、但し、該ポリカーボネートポリオールは、ポリテトラメチレングリコールポリオールに基づかない、ポリウレタン−ポリウレア水性分散体を提供する。
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.4)必要に応じて、ヒドロキシル基またはアミノ基を有する1以上の化合物、
I.5)1以上のイソシアネート反応性のイオン的または潜在的イオン的に親水性化する化合物、
I.6)必要に応じて、1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を反応させて、ウレア基不含イソシアネート官能性プレポリマーを調製する工程であって、イソシアネート反応性基に対するイソシアネート基のモル比が1.0〜3.5である工程、
b)該反応生成物を水中に分散する工程、および
c)水中での分散前、分散中または分散後に、残存するイソシアネート基をアミノ官能性鎖延長または連鎖停止する工程であって、前記プレポリマーの遊離イソシアネート基に対する鎖延長のために用いる化合物のイソシアネート反応性基の当量比が40%〜150%の間である工程
を含む、本発明のポリウレタンポリウレア水性分散体の製造方法を提供する。
H−Y’−X−Y−R (I)
〔式中、
Rは、1〜12個の炭素原子を有する1価炭化水素基、好ましくは1〜4個の炭素原子を有する未置換アルキル基であり、
Xは、少なくとも40%、好ましくは少なくとも65%の程度のエチレンオキシド単位に構成され得、およびエチレンオキシド単位に加えてプロピレンオキシド、ブチレンオキシドまたはスチレンオキシド単位から構成され得る(後述の単位は、好ましくはプロピレンオキシド単位である)、5〜90個、好ましくは20〜70個の鎖構成要素(chain members)を有するポリアルキレンオキシドであり、および
Y/Y’は、酸素であるか、または−NR’−であり、R’は、定義においてRまたは水素に相当する〕
で示される化合物である。
279.2gのDesmophen C−2200および14.9gのPolyether LB 25の混合物を、35.6gのDesmodur Iおよび26.9gのDesmodur Hと70℃で組み合わせ、105℃に加熱し、4.13%の一定のNCO値(理論値が4.18%である)が得られるまで105℃で撹拌した。該プレポリマーを631.7gのアセトンにより105℃で溶解し、20分間撹拌した。1.1gのヒドラジン水和物、6.8gのジアミノスルホネートおよび25gの水の混合物を42℃で6分間にわたり添加し、10分間撹拌した。12.7gのIPDAおよび63.6gの水の混合物を40℃で15分以内に添加し、10分間撹拌した。278.6gの水を40℃で15分以内に添加し、5分間、2.8gのIrganox 1010および2.8gのTinuvin 765の添加前に混合した。該混合物を10分間、アセトンを蒸留する前に混合した。最終分散体を50ミクロンフィルターによりろ過した。
Impranil DLU(Bayer AG、レーバークーゼン)のような、固形分60%および以下の物理特性を有するアニオン性脂肪族C4ポリエーテルポリカーボネートポリウレタン分散体:100%での弾性率=350psi、引張強度=3500psi、23℃での粘度(AFAM 2008/105、0304−00 D法に従う4mmカップ)<90秒。
Impranil DLN(Bayer AG、レーバークーゼン)のような、固形分40%および以下の物理特性を有するアニオン性脂肪族ポリエステルポリウレタン分散体:100%での弾性率=300psi、引張強度=2900psi、23℃での粘度(AFAM 2008/105、0304−00 D法に従う4mmカップ)<70秒。
上記の表に示された結果に基づいて、100%ポリカーボネートに基づく分散体は、市販の分散体、例えばImpranil DLUおよびImpranil DLN等よりも向上した加水分解安定性および保色性(ナイロン型編織布について)を示すと言うことができる。Impranil DLUは、C4ポリエーテルポリカーボネートジオールを用いて調製され、非常に良好な加水分解安定性を示すが、ナイロン型編織布についての保色性が低い。Impranil DLNは、ポリエステルジオールを用いて調製され、低い加水分解安定性および低い保色性を有する。
Claims (3)
- ポリウレタン−ポリウレア水性分散体を含む被覆材料をナイロン編織布に塗布する工程を含む、被覆ナイロン編織布の製造方法であって、該分散体は、以下の合成成分:
I.1)1以上のポリイソシアネート、
I.2)1000〜3000g/molの数平均分子量を有し、18〜56mgKOH/gのヒドロキシル価および1.8〜2.2のOH官能価を有する1以上のポリカーボネートポリオール、
I.3)62〜400g/molの分子量を有し、合計2以上のヒドロキシル基および/またはアミノ基を有する1以上の化合物、
I.5)スルホン酸またはその塩、および
I.6)1以上のイソシアネート反応性の非イオン的に親水性化する化合物
を含み、該分散体は、前記合成成分の合計重量を基準として60重量%〜90重量%の成分I.2)を含有し、但し、前記ポリカーボネートポリオールは、ポリテトラメチレングリコールポリオールに基づかない、方法。 - ポリウレタン−ポリウレア水性分散体は、成分I.1)5重量%〜40重量%、成分I.2)の合計60重量%〜90重量%、化合物I.3)0.5重量%〜20重量%、成分I.5)0.1重量%〜5重量および成分I.6)0重量%〜20重量%を含み、I.5)およびI.6)の合計が0.1重量%〜25重量%の間であり、全ての成分の合計が100重量%となる、請求項1に記載の方法。
- 請求項1または2に記載の方法によって製造された、被覆材料で被覆されたナイロン編織布。
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US13046808P | 2008-05-30 | 2008-05-30 | |
US61/130,468 | 2008-05-30 | ||
PCT/US2009/003239 WO2009148529A2 (en) | 2008-05-30 | 2009-05-27 | Polyurethane-polyurea dispersions based on polycarbonate-polyols |
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WO2012069414A1 (en) * | 2010-11-25 | 2012-05-31 | Bayer Materialscience Ag | Polyurethane resin with high carbonate group content |
PT3164437T (pt) * | 2014-07-02 | 2020-12-04 | Akzo Nobel Coatings Int Bv | Composições de revestimento de dois componentes e revestimentos fabricados à partir das mesmas para a melhoria da resistência à erosão |
CN104327696A (zh) * | 2014-10-21 | 2015-02-04 | 上海东方雨虹防水技术有限责任公司 | 一种聚碳酸酯多元醇型喷涂聚脲弹性体涂料及制备方法 |
WO2016104485A1 (ja) * | 2014-12-26 | 2016-06-30 | 旭化成株式会社 | ポリイソシアネート組成物及びその製造方法、ブロックポリイソシアネート組成物及びその製造方法、樹脂組成物、並びに硬化物 |
JP7129819B2 (ja) * | 2018-05-14 | 2022-09-02 | 東日本旅客鉄道株式会社 | 台車用カバー |
EP3825338A1 (en) * | 2019-11-20 | 2021-05-26 | Covestro Intellectual Property GmbH & Co. KG | Polyurethane-urea dispersions based on polycarbonate-polyols as coating compositions |
CN113773732B (zh) * | 2021-09-10 | 2022-05-17 | 苏州己申隆新材料科技有限公司 | 一种风电叶片用防覆冰超滑聚脲涂层及其制备方法和应用 |
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DE4222530A1 (de) * | 1992-07-09 | 1994-01-13 | Hoechst Ag | Polyurethan-Dispersionen |
JP3297503B2 (ja) * | 1993-07-26 | 2002-07-02 | 旭化成株式会社 | ポリウレタンエマルジョン |
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DE19643802A1 (de) * | 1996-10-30 | 1998-05-07 | Herberts Gmbh | Wäßrige Bindemitteldispersion für physikalisch trocknende Überzugsmittel und deren Verwendung |
US6455632B1 (en) * | 2000-12-05 | 2002-09-24 | Bayer Corporation | Aqueous polyurethane dispersions containing secondary amide groups and their use in one-component thermoset compositions |
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AU2004280360A1 (en) * | 2003-09-18 | 2005-04-21 | Bayer Materialscience Ag | Aqueous adhesive dispersions |
DE102004002526A1 (de) * | 2004-01-16 | 2005-08-04 | Bayer Materialscience Ag | Thermovergilbungsstabile Polyurethan-Polyharnstoff Dispersionen |
DE102004060139A1 (de) * | 2004-12-13 | 2006-06-29 | Bayer Materialscience Ag | Festkörperreiche Polyurethanpolyharnstoff-Dispersionen |
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US7452525B1 (en) * | 2007-08-08 | 2008-11-18 | Yuliya Berezkin | Polyurethane dispersions based on polycarbonate polyols and suitable for use in personal care products |
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CN102046683A (zh) | 2011-05-04 |
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