JP2020518715A - セルロース誘導体 - Google Patents
セルロース誘導体 Download PDFInfo
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- JP2020518715A JP2020518715A JP2020512090A JP2020512090A JP2020518715A JP 2020518715 A JP2020518715 A JP 2020518715A JP 2020512090 A JP2020512090 A JP 2020512090A JP 2020512090 A JP2020512090 A JP 2020512090A JP 2020518715 A JP2020518715 A JP 2020518715A
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- cellulose
- derivatization
- reaction
- water
- pulp
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- C08B1/00—Preparatory treatment of cellulose for making derivatives thereof, e.g. pre-treatment, pre-soaking, activation
- C08B1/02—Rendering cellulose suitable for esterification
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Abstract
Description
現在のところ、誘導体化を促進するフィブリルレベルまでセルロース繊維を膨潤し、浸透できる試薬を用いてセルロースを誘導体化する一般的な乾燥、半乾燥、または高固形分の方法はない。
a.尿素および少なくとも1つの誘導体化試薬を含む反応媒体を用意すること。
b.反応媒体と接触しているセルロースパルプを含む反応系において、少なくとも1つの誘導体化試薬とセルロースパルプとの間の化学的誘導体化反応を行うこと;ならびに
c.任意に、誘導体化セルロース生成物を精製および/または回収すること。
水含有量が0〜20重量%の反応系、または
水含有量が10〜20重量%の反応系
においてセルロースパルプで行われる。
カチオン性サンプルのDSは、0.01MのAgNO3による塩化物イオンの導電率滴定によって決定され、通常、40gの均質化された0.5%カチオン性セルロース懸濁液を蒸留水で250mlに希釈した。滴定は、1〜5mlの0.01MのAgNO3溶液を添加することによって絶えず撹拌しながら実施し、1分後に導電率を記録した。滴定は、導電率の最小値に達するまで実施され、最小値を通過した後、少なくとも5回のAgNO3の添加が記録された。最小点は、サンプル中の塩化物イオンの総量を表し、上昇および下降の導電率傾向線の交点から計算された。
カチオン化は、カチオン化試薬と組み合わせた膨潤剤を使用して行われた。尿素プリル(6.0g)(99%)、グリシジルトリメチルアンモニウムクロリド溶液(10.1g)(73%活性エポキシ)および水(2.5g)を計量し、溶液が形成されるまで撹拌した。NaOH(0.5g)(50重量%)を添加し、得られた溶液18.8gを溶解パルプ(10.2g)(Borregaard Ice−Bear P Aceta)のシートに含浸させ、セルロース(34.5%)、GTMA(25.0%)、尿素(20.3%)、NaOH(0.9%)および水(19.3%)の反応組成物を得た。膨潤/反応は、密閉されたポリエチレンバッグ内で40℃で3日間行われた。誘導体化セルロースは最終的に蒸留水に懸濁され、繰り返し濾過により洗浄された。次いで、サンプルを高圧均質化によりナノフィブリル化した。
誘導体化反応は、溶解パルプをシュガー・ビート・パルプに置き換えて例1として行う。誘導体化溶液は、混練によりパルプに混合され、ペレット形態に押し出され、水分含有量が20〜30%になるまで乾燥される。次いで、反応を40℃で3日間進行させて、カチオン性柔細胞セルロースを得る。
硫酸(9.0g)(96%)を5mlの蒸留水に注意深く溶解した。尿素プリル(11.0g)(99%)を添加し、溶液が形成されるまで撹拌した。得られた溶液23gを木材パルプ(10g)のシートに浸し、室温で一晩乾燥させて、セルロース(34.0%)、硫酸(27.6%)、尿素(35.1%)および水(3.2%)の組成物を得た。得られたシートを対流式オーブンにて150℃で15分間加熱した。得られた誘導体化セルロースをアセトン/水2:1で2回洗浄し、アセトン/水/NaOH pH=12で1回洗浄し、再びアセトン/水2:1で2回洗浄し、最後に蒸留水に分散させ、高圧均質化でフィブリル化して、硫酸化セルロースナノ結晶の無色透明懸濁液を得た。
誘導体化反応は、溶解パルプをシュガー・ビート・パルプに置き換えて、例4として行う。誘導体化溶液は、混練によりパルプに混合され、ペレット形態に押し出され、水分含有量が3〜10%になるまで乾燥される。次いで、反応を150℃で15分間進行させて、硫酸化柔細胞セルロースを得る。
硫酸を蒸留水で希釈した(サンプルSUL−1)。別のサンプル(SUL−2、SUL−3、SUL−4))では、希釈液をNaOHまたはアンモニア溶液で少なくとも部分的に中和した。尿素プリルを添加し、溶液が形成されるまで撹拌した。得られた溶液を木材パルプのシートに浸し、水分含有量が2重量%未満になるまで室温で乾燥させて、表2に記載の試薬比を得た。次いで、材料を対流式オーブンで所望の温度および時間で加熱して、硫酸セルロースを得た(スキーム1)。得られた誘導体化セルロースをエタノール/水2:1で3回洗浄し、最後に蒸留水に分散させ、高圧均質化でフィブリル化した。
スキーム1。生成された硫酸セルロースの化学構造。
漂白実験は、NaOH溶液をセルロース誘導体の水懸濁液に添加し、混練して混合してpHを10〜11に調整することで行った。濃H2O2を添加し、次いで懸濁液に混合した。次いで、サンプルを室温で24時間または80℃で1時間反応させた。前の例で説明した方法で生成された均質化および非均質化硫酸セルロースサンプル両方を試験した。
Claims (28)
- セルロースパルプを誘導体化する方法であって、
a.尿素および少なくとも1つの誘導体化試薬を含む反応媒体を用意すること、
b.前記反応媒体と接触している前記セルロースパルプを含む反応系において、前記少なくとも1つの誘導体化試薬と前記セルロースパルプとの間の化学的誘導体化反応を行うこと、ならびに
c.任意に、誘導体化セルロース生成物を精製および/または回収すること
を含む、方法。 - 前記化学的誘導体化反応が、
水含有量が0〜20重量%の反応系、または
水含有量が10〜20重量%の反応系
において前記セルロースパルプで行われる、請求項1に記載の方法。 - 前記反応系が、マーセル化されていないか、または酵素的もしくは機械的に前処理されていないセルロースパルプを使用して調製される、請求項1または2に記載の方法。
- 前記誘導体化試薬が硫酸化試薬であり、前記反応媒体が0〜10重量%の水を含む、請求項1〜3のいずれかに記載の方法。
- 工程a.が、硫酸を水に溶解させ、それをアルカリで少なくとも部分的に中和し、続いて尿素を添加することを含む、請求項4に記載の方法。
- 前記スルホン化試薬が硫酸水素塩および任意に硫酸を含む、請求項4に記載の方法。
- 前記工程c.が水で洗浄することを含み、洗浄された生成物がフィブリル化される、請求項4〜6のいずれかに記載の方法。
- フィブリル化の前または後に行われる漂白工程を含む請求項7に記載の方法。
- 前記誘導体化試薬がカチオン化試薬であり、前記反応媒体が10〜20重量%の水を含む、請求項1〜3のいずれかに記載の方法。
- 前記工程b.の前または間に、水が、0〜20重量%の範囲から選択された水分含有量まで除去される、請求項1〜9のいずれかに記載の方法。
- 前記セルロースパルプに前記反応媒体を含浸させることにより前記反応系が調製される、請求項1〜10のいずれかに記載の方法。
- 前記工程a、bおよびcの少なくとも1つが連続プロセスを使用して実施される、請求項1〜11のいずれかに記載の方法。
- 前記セルロースパルプの無水グルコース単位に対する前記誘導体化試薬のモル比が、0.01〜8、好ましくは0.1〜2、最も好ましくは0.3〜1.5である、請求項1〜12のいずれかに記載の方法。
- 前記セルロースパルプの無水グルコース単位に対する尿素のモル比が、0.01〜8、好ましくは0.1〜5、最も好ましくは0.3〜3である、請求項1〜13のいずれかに記載の方法。
- 前記セルロースパルプの無水グルコース単位に対する水のモル比が、0〜20、好ましくは0.1〜10、最も好ましくは3〜7である、請求項1〜14のいずれかに記載の方法。
- 前記反応系が塩基触媒を含み、前記セルロースパルプの無水グルコース単位に対する前記塩基触媒のモル比が、0〜20、好ましくは0.01〜10、最も好ましくは0.05〜2である、請求項1〜15のいずれかに記載の方法。
- イオン液体;塩;深共晶溶媒;カルバミド部分、過酸化カルバミド部分、アラントイン部分、ヒドラトイン部分、ビウレットを含む化合物、およびそれらの組み合わせから選択される少なくとも1つの膨潤剤を前記反応系に提供することをさらに含む、請求項1〜16のいずれかに記載の方法。
- 前記誘導体化の程度が、前記試薬の量および/または反応パラメータによって制御される、請求項1〜17のいずれかに記載の方法。
- 前記誘導体化反応が、0.05〜2.5mmol/g、好ましくは0.1〜1.5mmol/g、最も好ましくは0.5〜1.3mmol/gの誘導体化の程度まで行われる、請求項1〜18のいずれかに記載の方法。
- 前記誘導体化反応が、セルロースパルプの基本フィブリルの表面上で主に不均一に行われる、請求項1〜19のいずれかに記載の方法。
- 前記誘導体化の程度を高めるための、または追加の官能基を導入するための、さらなる化学修飾工程−好ましくはエステル化およびエーテル化から選択される−を含む、請求項1〜20のいずれかに記載の方法。
- 好ましくはカチオン化または硫酸化から選択されるさらなる化学修飾工程を含む、請求項1〜21のいずれかに記載の方法。
- 前記セルロースパルプが、広葉樹パルプもしくは針葉樹パルプ、溶解パルプ、または柔細胞セルロースパルプを含む任意の適切な植物材料から抽出されたセルロースパルプである、請求項1〜22のいずれかに記載の方法。
- 誘導体化セルロースナノファイバーまたは誘導体化ミクロフィブリル化セルロースを得るための精製工程をさらに含む、請求項1〜23のいずれかに記載の方法。
- 中稠度生成物、高稠度生成物、または乾燥生成物を得るための乾燥工程をさらに含む、請求項1〜24のいずれかに記載の方法。
- 請求項1〜24のいずれかに記載の方法によって得られ、100rpmの剪断速度にて1.0重量%の濃度で測定される場合少なくとも10cP、好ましくは少なくとも100cPのブルックフィールド粘度および/または0.1重量%濃度で測定される場合1000NTU未満、好ましくは0.1〜700NTUの範囲の濁度値を有する誘導体化セルロース生成物。
- 請求項1〜25のいずれかに記載の方法によって得られた誘導体化セルロース生成物であって、前記誘導体化の程度が0.05〜2.5mmol/g、好ましくは0.1〜1.5mmol/g、最も好ましくは0.5〜1.3mmol/gである、生成物。
- 請求項1〜25のいずれかに記載の方法によって得られた誘導体化セルロース生成物であって、前記生成物が、1重量%濃度で測定される場合0〜120℃の温度でpH2〜13にて水に不溶性である、生成物。
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