JP2021514419A - 優れた熱変形耐性および引裂伸びを有するポリウレタンベースのポリマー材料 - Google Patents
優れた熱変形耐性および引裂伸びを有するポリウレタンベースのポリマー材料 Download PDFInfo
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- JP2021514419A JP2021514419A JP2020544620A JP2020544620A JP2021514419A JP 2021514419 A JP2021514419 A JP 2021514419A JP 2020544620 A JP2020544620 A JP 2020544620A JP 2020544620 A JP2020544620 A JP 2020544620A JP 2021514419 A JP2021514419 A JP 2021514419A
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- Prior art keywords
- carbon
- isocyanate
- compound
- polyurethane
- carbon double
- Prior art date
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- FUSUHKVFWTUUBE-UHFFFAOYSA-N vinyl methyl ketone Natural products CC(=O)C=C FUSUHKVFWTUUBE-UHFFFAOYSA-N 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 238000004046 wet winding Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
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- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/6696—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/36 or hydroxylated esters of higher fatty acids of C08G18/38
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- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
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- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
-
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/4804—Two or more polyethers of different physical or chemical nature
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- C08G18/00—Polymeric products of isocyanates or isothiocyanates
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- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
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Abstract
Description
ポリウレタンをベースとするプリプレグが既知である。これはブロック化ポリイソシアネートをベースとし、例えばWO11147688、WO10108701およびWO10108723に記載されている。しかしながら、この方法では比較的高い粘度がもたらされるので、含浸中に不利な結果となる。さらに、ブロック化触媒の使用は、WO2013139704に記載されているように、非常に高いイソシアネート指数を必要とする。この高いイソシアネート過剰は、湿度に対する感受性の増加をもたらす。従って、既知のプリプレグは、空気を排除した真空バッグ内に好ましくは貯蔵する。
出発材料(データはすべての表中で質量%)。通常のバッチサイズ:ポリオール成分300gを室温で混合した。次いでイソシアネートを添加して混合物を高速ミキサー(FA Hauschild)で60秒間混合した。次に反応混合物を20×30×0.4cmまたは20×30×0.2cmの金型に入れた。ドクターブレードですくい取って余剰樹脂を除去し、硬化を80℃で1時間、次いで120℃で2時間、および170℃で2時間行った。室温で1週間保管した後、材料から試験片を粉砕した。
実施例2の出発材料、および比較例1をそれぞれ室温で混合した。次いでイソシアネートを添加して混合物を高速ミキサー(FA Hauschild)で60秒間混合した。次に反応混合物を20×30×0.4cmまたは20×30×0.2cmの金型に入れた。ドクターブレードを使用して、余剰樹脂をすくい取り除去した。反応混合物を40℃で1時間硬化させた。次いで、耐熱性を測定するために、測定値4mm×80mm×10mmの試験片を打ち抜いた。この試験片の一部は、耐熱性を測定する前に、表2のデータに従って熱調整を行った。結果は、反応プロファイルを示していた。遊離ラジカル阻害剤の存在下では、80℃未満の温度で部分的な反応しか起こっていなかった。この状態で反応生成物は貯蔵可能であり、粘性であった。>120℃のより高い温度の結果として、本発明の実施例の熱変形温度は、100℃を超える著しい上昇を示し、この時初めて最終的な特性が達成された。完全に硬化(160℃)する本発明の実施例の熱変形温度は、遊離ラジカル開始剤を有する比較例1の熱変形温度(120℃)よりも著しく高い。
積層体(一方向性の前含浸した半完成織物製品)の製造:
出発材料(表5)を室温で混合した。次いで、計量システムを使用して、反応混合物を室温で連続的に開放浴に入れた。使用した前含浸方法は、湿式巻取りプロセスをベースとした。合計42本のロービング(外部取り外し(external take-off)、各ロービングにヤーンブレーキを使用)のTex2400を、最初に穿孔金属シートに通過させ、次いで含浸浴中に連続的に通した。含浸装置に統合されたスクレーパーですくい取り、余剰樹脂を除去した。これにより余剰樹脂は浴内に送り戻すことができ、これにより含浸させたロービングから樹脂が滴るのが回避される。含浸させたロービングを、測定値5.5×0.2cmの金属製の穴に通過させ、剥離紙の間に挟んで80℃で硬化した。加熱ユニットを通過させた後、得られた幅5.5cmの一方向性のプリプレグをリールに巻き取ることができた。
ポリオール2:分岐脂肪酸エステル、OHN173、粘度3400mPas(25℃)
ポリオール3:非NCO反応性脂肪酸エステル、粘度7mPas(25℃)
ポリオール4:スクロースおよびグリセロールのプロポキシル化混合物、OHN490、官能価4.4、粘度8450mPas(25℃)
ポリオール5:プロポキシル化グリセロール、OHN805、粘度1275mPas(25℃)
ポリオール6:プロポキシル化グリセロール、OHN400、粘度375mPas(25℃)
ポリオール7:プロポキシル化プロピレングリコール、OHN248、粘度75mPas(25℃)
ポリオール8:ヒマシ油、OHN160、粘度1025mPas(25℃)
ポリオール9:カチオン性プロポキシル化グリセロール、OHN555、粘度690mPas(25℃)
TMPTA:トリメチロールプロパントリアクリレート
触媒1:DPG中の酢酸カリウム40%溶液
遊離ラジカル開始剤1:ベンゾイルペルオキシド
遊離ラジカル阻害剤1:フェノチアンジン
消泡剤1:Efka SI2008、BASF SE
消泡剤2:Efka SI2723、BASF SE
イソシアネート1:4,4’−MDI、ジプロピレングリコール/ポリプロピレングリコールをベースとするプレポリマーと、カルボジイミド修飾4,4’−MDIとの1:1混合物、NCO含有量26%
イソシアネート2:ポリマーMDIと、2,4’−MDIおよび4,4’−MDIの1:1混合物との1:1混合物、NCO含有量32.5%
DIN53019−1〜3に準拠した粘度
DIN ISO7619−1に準拠したショアD硬度試験
DIN EN ISO178に準拠した3点曲げ試験
DIN EN ISO527に準拠した引張強さ
DIN EN ISO179−1/1fUに準拠したシャルピー衝撃耐性(平面方向)
熱変形温度:DIN EN ISO75に準拠したHDT−B−f、外繊維応力0.45MPaでの平面方向3点曲げ
Claims (14)
- a. ジイソシアネートおよび/またはポリイソシアネートと、
b. イソシアネート基に対して反応性のある水素原子を有し、炭素−炭素二重結合が含まれない化合物と、
c. 少なくとも1つの炭素−炭素二重結合を含む化合物と、
d. 任意に、ウレタン反応を促進する触媒と、
e. 任意に、他の助剤および添加剤
とを混合して反応混合物を得て、120℃より上の温度で硬化させる、ポリウレタン材料の製造方法であって、
イソシアネートに対して反応性のある水素原子を有する化合物b)が、1分子当たり、イソシアネートに対して反応性のある平均で少なくとも1.5個の水素基を有し、
炭素−炭素二重結合を有する化合物(c)が、少なくとも1つの炭素−炭素二重結合とイソシアネートに対して反応性のある基から選択されるかまたはイソシアネート基から選択される少なくとも1つの基とを有するこのタイプの化合物(c1)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(c2)を含み、
前記反応混合物が安定化されている、製造方法。 - ジイソシアネートおよび/またはポリイソシアネート(a)のイソシアネート基の、前記イソシアネートに対して反応性のある水素原子に対する当量比が、0.7〜1.4である、請求項1に記載の方法。
- 化合物(c)の全量に基づく、化合物(c1)及び(c2)の全体の割合が、5〜100モル%である、請求項1または2に記載の方法。
- 化合物(c)のモル質量が1000g/モル未満である、請求項1から3のいずれか一項に記載の方法。
- 化合物(c1)および(c2)が、炭素−炭素二重結合に基づいて、60〜100%の末端炭素−炭素二重結合を有する、請求項1から4のいずれか一項に記載の方法。
- ジイソシアネートおよび/またはポリイソシアネート(a)が、官能価が2のイソシアネートを少なくとも50モル%含む、請求項1から5のいずれか一項に記載の方法。
- 使用するジイソシアネートおよび/またはポリイソシアネート(a)が、2,4’−MDI、4,4’−MDI、またはこれらの成分の、任意に、より多数の環を有するMDIのホモログとの混合物を含む、請求項1から6のいずれか一項に記載の方法。
- 前記反応混合物が、0.001〜1.0質量%の遊離ラジカル阻害剤を含む、請求項1から7のいずれか一項に記載の方法。
- 前記反応混合物が塩基性触媒を含む、請求項1から8のいずれか一項に記載の方法。
- 炭素−炭素二重結合を有する化合物(c)の割合が、成分(a)〜(e)の総質量に基づいて10〜70質量%である、請求項1から9のいずれか一項に記載の方法。
- イソシアネートに対して反応性のある水素原子を有するポリマー化合物(b)または(c)が、疎水性基を有する少なくとも1つのヒドロキシ官能性化合物を含む、請求項1から10のいずれか一項に記載の方法。
- 前記反応混合物の反応を、第1段階で少なくとも10分間、120℃未満の温度で実施し、次いで前記混合物を150℃より上の温度で硬化させる、請求項1から11のいずれか一項に記載の方法。
- 前記ポリウレタン材料がポリウレタン繊維複合材料であり、繊維材料を前記反応混合物で濡らし、次いで前記混合物を硬化させて、前記ポリウレタン繊維複合材料が得られる、請求項1から12のいずれか一項に記載の方法。
- 請求項1から13のいずれか一項に記載の方法によって得ることができるポリウレタン材料。
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KR20200125965A (ko) | 2020-11-05 |
EP3755735A1 (de) | 2020-12-30 |
CN111757899B (zh) | 2023-01-17 |
PH12020551287A1 (en) | 2021-07-12 |
US20200399418A1 (en) | 2020-12-24 |
AU2019225884B2 (en) | 2024-02-15 |
EA202091902A1 (ru) | 2020-12-10 |
AU2019225884C1 (en) | 2024-06-06 |
MX2020008799A (es) | 2020-10-14 |
JP7359520B2 (ja) | 2023-10-11 |
CN111757899A (zh) | 2020-10-09 |
BR112020016339A2 (pt) | 2021-03-02 |
CA3091506A1 (en) | 2019-08-29 |
WO2019162115A1 (de) | 2019-08-29 |
AU2019225884A1 (en) | 2020-09-03 |
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