JP5675587B2 - 生分解可能なポリエステルを連続的に製造する方法 - Google Patents
生分解可能なポリエステルを連続的に製造する方法 Download PDFInfo
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- JP5675587B2 JP5675587B2 JP2011504420A JP2011504420A JP5675587B2 JP 5675587 B2 JP5675587 B2 JP 5675587B2 JP 2011504420 A JP2011504420 A JP 2011504420A JP 2011504420 A JP2011504420 A JP 2011504420A JP 5675587 B2 JP5675587 B2 JP 5675587B2
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- polyester
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Classifications
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/4208—Polycondensates having carboxylic or carbonic ester groups in the main chain containing cyclic groups containing aromatic groups
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
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- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4236—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups
- C08G18/4238—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols
- C08G18/4241—Polycondensates having carboxylic or carbonic ester groups in the main chain containing only aliphatic groups derived from dicarboxylic acids and dialcohols from dicarboxylic acids and dialcohols in combination with polycarboxylic acids and/or polyhydroxy compounds which are at least trifunctional
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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
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- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/73—Polyisocyanates or polyisothiocyanates acyclic
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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
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- C08G63/127—Acids containing aromatic rings
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/16—Dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
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- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/20—Polyesters having been prepared in the presence of compounds having one reactive group or more than two reactive groups
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Description
脂肪族ジヒドロキシ化合物、脂肪族ジカルボン酸および芳香族ジカルボン酸、および場合によっては他のコモノマー(成分C)からなる混合物は、触媒の添加なしに混合されてペーストを生じるか、または他の選択可能な方法によれば、ジカルボン酸の液状エステルおよびジヒドロキシ化合物、および場合によっては他のコモノマーは、触媒の添加なしに供給され、および
i)第1工程で前記混合物は、触媒の全質量または部分量と一緒に連続的にエステル化されるかまたはエステル交換され;
ii)第2工程で場合によっては残量の触媒でi)により得られたエステル交換生成物またはエステル化生成物は、20〜70cm3/gのDIN 53728による粘度数になるまで連続的に前縮合され;
iii)第3工程でii)から得られた生成物が60〜170cm3/gのDIN 53728による粘度数になるまで連続的に重縮合され、および
iv)第4工程でiii)から得られた生成物が150〜320cm3/gのDIN 53728による粘度数になるまで重付加反応で鎖長延長剤Dと連続的に反応される。
脂肪族ジヒドロキシ化合物、脂肪族ジカルボン酸および芳香族ジカルボン酸、および場合によっては他のコモノマー(成分C)からなる混合物は、触媒の添加なしに混合されてペーストを生じるか、または他の選択可能な方法によれば、ジカルボン酸の液状エステルおよびジヒドロキシ化合物、および場合によっては他のコモノマーは、触媒の添加なしに供給され、この場合
i)第1工程で前記混合物は、触媒の全質量または部分量と一緒に連続的にエステル化されるかまたはエステル交換され;
ii)第2工程で場合によっては残量の触媒でi)により得られたエステル交換生成物またはエステル化生成物は、20〜70cm3/gのDIN 53728による粘度数になるまで連続的に前縮合され;
iii)第3工程でii)から得られた生成物が70〜130cm3/gのDIN 53728による粘度数になるまで連続的に重縮合され、および
iv)第4工程でiii)から得られた生成物が160〜250cm3/gのDIN 53728による粘度数になるまで重付加反応で鎖長延長剤Dと連続的に反応される。
A)
a1)少なくとも1つの脂肪族ジカルボン酸またはそのエステル、またはその混合物30〜99モル%、
a2)少なくとも1つの芳香族ジカルボン酸またはそのエステル、またはその混合物1〜70モル%および
a3)スルホネート基含有化合物0〜5モル%からなる酸成分、
この場合成分a1)〜a3)のモル%は、全部で100%であり、および
B)
b1)成分Aに対して少なくとも当モル量のC2〜C12アルカンジオールまたはその混合物および
b2)工程iiiによるポリエステル量(分離された反応蒸気を差し引いて成分AおよびBの使用された量に相当する)に対して0〜2質量%の少なくとも3個の官能基を含有する化合物からなるジオール成分、および場合によってはさらに
C)
c1)式I
HO−[(CH2)n−O]m−H (I)
〔式中、nは、2、3または4を表わし、mは、2〜250の整数を表わす〕で示されるエーテル官能基を含有する少なくとも1つのジヒドロキシ化合物、
c2)式IIaまたはIIbで示される少なくとも1つのヒドロキシカルボン酸、
c3)少なくとも1つのアミノ−C2〜C12アルカノールまたは少なくとも1つのアミノ−C5〜C10シクロアルカノール、またはその混合物、
c4)少なくとも1つのジアミノ−C1〜C8アルカン、
c5)カプロラクタム、1,6−アミノカプロン酸、ラウリンラクタム、1,12−アミノラウリン酸および1,11−アミノウンデカン酸からなる群から選択された少なくとも1つのアミノカルボン酸化合物またはc1〜c5)からなる混合物から選択された成分、および
D)工程iii後のポリエステル量に対して0.01〜4質量%の群d1)〜d4)
d1)二官能性またはオリゴ官能性イソシアネートおよび/またはイソシアヌレート、
d2)二官能性またはオリゴ官能性ペルオキシド、
d3)二官能性またはオリゴ官能性エポキシド、
d4)二官能性またはオリゴ官能性オキサゾリン、オキサジン、カプロラクタムおよび/またはカルボジイミドから選択された少なくとも1つの成分;
E)工程iii後のポリエステル量に対して0〜15質量%の群e1)〜e3)
e1)滑剤、例えばエルカ酸アミドまたはステアレート、
e2)成核剤、例えば炭酸カルシウム、ポリエチレンテレフタレートまたはポリブチレンテレフタレート、
e3)次のもの:ポリ乳酸、ポリカプロラクトン、ポリヒドロキシアルカノエートからなる群から選択された脂肪族ポリエステルから選択された成分から形成されている。
加工中、例えば澱粉との配合中のよりいっそう少ない分子量の減少、
よりいっそう良好な貯蔵安定性、
フィルム製造の際のよりいっそう良好な溶融液安定性および
高い分子量による、射出成形および殊に押出の際の優れた使用特性を有する。
生成物流を搬送するためのポンプをできる限り省略することができ;生成物の流出は、重量測定による流れとして簡単に制御することができ;反応器は、弱い過圧、常圧または僅かな低圧で(上記参照)運転されることができ、
反応混合物からの現場で(in situ)の反応蒸気の連続的な導出は、平衡を既に極めて穏和な運転形式で反応生成物の側に移行する。更に、反応蒸気の急速な導出によって、副反応は、回避されるか、または少なくとも抑制される。
一般に、上記の運転形式で25〜55cm3/gのDIN 53728による粘度数を有する脂肪族/芳香族プレポリエステルは、製造することができる。更に、このプレポリエステルは、DIN EN 12634による極めて低い酸価を有する。
酸価は、1998年10月のDIN EN 12634により測定された。溶剤混合物として、DMSO1体積部、プロパン−2−オール8体積部およびトルエン7体積部からなる混合物が使用された。試料は、50℃に加熱され、塩化カリウム充填物を有する棒電極と結合された。基準溶液として、テトラメチルアンモニウム−ヒドロキシド基準溶液が使用された。
1.HDIで鎖長延長されたポリブチレンアジペート−コ−テレフタレートの連続的製造(請求項1から4までのいずれか1項に記載の方法)
生分解可能なポリエステルの製造のために、ジメチルテレフタレート440kg/h、アジピン酸および1,4−ブタンジオールからなるプレポリエステル510kg/h(Mn2000g/mol)、1,4−ブタンジオール270kg/hおよびグリセリン1.0kg/hをテトラブチルオルトチタネート0.55kg/hと一緒に連続的に多段の攪拌釜型カスケード中に供給した。反応混合物を常圧で攪拌釜型カスケード内で180℃〜210℃の温度および2.5時間の滞留時間でエステル交換し、生じる縮合生成物メタノールを留去した。こうして得られた低分子量のポリエステルは、10cm3/gの粘度数(VZ)を有していた。
生分解可能なポリエステルの製造のために、テレフタル酸19kg/h、アジピン酸19kg/h、1,4−ブタンジオール32kg/hおよびグリセリン0.05kg/hを35℃で物理的に混合し、引続きこの混合物を連続的にエステル化釜中(例えばWO 03/042278A1の記載と同様に液体サイクロンとして設計された)に移行させた。更に、1,4−ブタンジオール16kg/hおよびテトラブチルオルトチタネート0.022kg/h(TBOT)の添加下に、前記混合物を240℃の温度、1.5時間の滞留時間および0.85バールの圧力でエステル化し、生じる縮合生成物の水、ならびに過剰量のブタンジオールの一部分を留去した。こうして得られた低分子量のポリエステルは、12cm3/gの粘度数(VZ)を有していた。引続き、この反応混合物をさらにTBOT0.012kg/時間の添加下に250℃から265℃へ上昇する温度、2時間の滞留時間および300ミリバールから10ミリバールへ減少する圧力で落下流式カスケード(例えば、WO 03/042278 A1の記載と同様)上に導き、過剰量のブタンジオールの主要部を留去した。こうして得られたポリエステルは、47cm3/gの粘度数(VZ)を有していた。
生分解可能なポリエステルの製造のために、ジメチルテレフタレート3700kg、アジピン酸と1,4−ブタンジオールとからなるプレポリエステル4300kg(Mn2000g/mol)、1,4−ブタンジオール2200kg、グリセリン8.5kgおよびテトラブチルオルトチタネート2.4kgを攪拌釜中に供給した。過剰量の1,4−ブタンジオールを留去しながら、反応混合物を8時間で段階的に245℃の温度に加熱し、同時に圧力を段階的に5ミリバールに減少させた。引続き、真空下で亜燐酸0.6kgを攪拌しながら添加した。こうして得られたポリエステルは、91cm3/gの粘度数(VZ)および1,3mg KOH/gの酸価(SZ)を有していた。重縮合に引き続いて、ポリエステルに240℃でヘキサメチレンジイソシアネート6.8kg/h(HDI)を静的混合系を用いて供給した。7分間の滞留時間後、ポリエステルを水中造粒を用いて造粒し、および乾燥させた。こうして得られたポリエステルは、170cm3/gのVZ、32000g/molの分子量Mn(または95000g/molのMw)、6.0cm3/10分のMVRおよび1.5mg KOH/gのSZを有していた。
Claims (20)
- 脂肪族ジカルボン酸または脂肪族ジカルボン酸および芳香族ジカルボン酸ならびに脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステルを連続的に製造する方法であって、この場合
脂肪族ジヒドロキシ化合物、脂肪族ジカルボン酸および芳香族ジカルボン酸、および場合によっては他のコモノマー(成分C)からなる混合物は、触媒の添加なしに混合されてペーストを生じるか、または他の選択可能な方法によれば、ジカルボン酸の液状エステルおよびジヒドロキシ化合物、および場合によっては他のコモノマーは、触媒の添加なしに供給され、この場合
i)第1工程で前記混合物は、触媒の全質量または部分量と一緒に連続的にエステル化されるかまたはエステル交換され、ここで前記触媒はチタン触媒であり;
ii)第2工程でi)により得られたエステル交換生成物またはエステル化生成物は、20〜70cm3/gのDIN 53728による粘度数になるまで連続的に前縮合され、ここで工程ii)を塔型反応器中で実施し、生成物流を反応蒸気と並流で多段の流下薄膜式蒸発器へ導き、反応蒸気をその場で反応混合物から除去し;
iii)第3工程でii)から得られた生成物が60〜170cm3/gのDIN 53728による粘度数になるまで連続的に重縮合され、および
iv)第4工程でiii)から得られた生成物が150〜320cm3/gのDIN 53728による粘度数になるまで重付加反応で鎖長延長剤Dと連続的に反応され、ここで工程iv)を押出機、リスト反応器または静的混合機中で実施する、
脂肪族ジカルボン酸または脂肪族ジカルボン酸および芳香族ジカルボン酸ならびに脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステルを連続的に製造する方法。 - 生分解可能なポリエステルが:
A)
a1)少なくとも1つの脂肪族ジカルボン酸またはそのエステル、またはその混合物30〜99モル%、
a2)少なくとも1つの芳香族ジカルボン酸またはそのエステル、またはその混合物1〜70モル%および
a3)スルホネート基含有化合物0〜5モル%からなる酸成分、
この場合成分a1)〜a3)のモル%は、全部で100%であり、および
B)
b1)成分Aに対して少なくとも当モル量のC2〜C12アルカンジオールまたはその混合物および
b2)成分Aおよびb1)に対して0〜2質量%の少なくとも3個の官能基を含有する化合物からなるジオール成分から形成され;および
場合によってはさらに
C)
c1)式I
HO−[(CH2)n−O]m−H (I)
〔式中、nは、2、3または4を表わし、mは、2〜250の整数を表わす〕で示されるエーテル官能基を含有する少なくとも1つのジヒドロキシ化合物、
c2)式IIaまたはIIb
c3)少なくとも1つのアミノ−C2〜C12アルカノールまたは少なくとも1つのアミノ−C5〜C10シクロアルカノール、またはその混合物、
c4)少なくとも1つのジアミノ−C1〜C8アルカン、
c5)カプロラクタム、1,6−アミノカプロン酸、ラウリンラクタム、1,12−アミノラウリン酸および1,11−アミノウンデカン酸からなる群から選択された少なくとも1つのアミノカルボン酸化合物
またはc1)〜c5)からなる混合物
から選択された成分;
および
D)工程iii)後のポリエステル量に対して0.01〜4質量%の群d1)〜d4)
d1)二官能性またはオリゴ官能性イソシアネートおよび/またはイソシアヌレート、
d2)二官能性またはオリゴ官能性ペルオキシド、
d3)二官能性またはオリゴ官能性エポキシド、
d4)二官能性またはオリゴ官能性オキサゾリン、オキサジン、カプロラクタムおよび/またはカルボジイミド、
から選択された少なくとも1つの成分;
E)工程iii)後のポリエステル量に対して0〜10質量%の群e1)〜e3)
e1)滑剤、
e2)成核剤、
e3)次のもの:ポリ乳酸、ポリカプロラクトン、ポリヒドロキシアルカノエートからなる群から選択された脂肪族ポリエステル、
から選択された成分;
から選択された1つ以上の成分から形成される、請求項1記載の方法。 - 生分解可能なポリエステルは、
脂肪族ジカルボン酸(成分a1))としてコハク酸、アジピン酸またはセバシン酸、そのエステルまたはその混合物;
芳香族ジカルボン酸(成分a2))としてテレフタル酸またはそのエステル;
ジオール成分(成分B)として、1,4−ブタンジオールまたは1,3−プロパンジオール、
成分b2)としてグリセリン、ペンタエリトリット、トリメチロールプロパンおよび
成分d1)としてヘキサメチレンジイソシアネートを含有する、請求項1記載の方法。 - エステル化/エステル交換(工程i))を液体サイクロンの形で、付随する熱交換器を用いて実施し、工程i)、ii)およびiii)をチタン触媒の存在下で実施する、請求項1から3までのいずれか1項に記載の方法。
- 工程ii)において、エステル交換生成物またはエステル化生成物を25〜55cm3/gのDIN 53728による粘度数になるまで前縮合する、請求項1から4までのいずれか1項に記載の方法。
- 工程ii)とiii)の間で生成物流に、不活性にする燐化合物0.001〜0.1質量%または色安定にするかまたは活性化する燐化合物0.001〜1.5質量%を添加する、請求項1から5までのいずれか1項に記載の方法。
- 工程iii)の開始時、工程iii)中または工程iii)の終結時、または鎖長延長ivb)に対して前方の工程iva)で、二官能性またはオリゴ官能性エポキシド(d3)、オキサゾリン、オキサジン、カプロラクタムおよび/またはカルボジイミド(d4)の群から選択された酸捕捉剤を、それぞれポリマー材料に対して0.01〜2.0質量%添加する、請求項1から5までのいずれか1項に記載の方法。
- 工程iii)を回転ディスク型反応器またはかご形反応器中で実施する、請求項1から7までのいずれか1項に記載の方法。
- 工程iii)後に滑剤e1を工程iii)後のポリマー材料に対して0.05〜2.0質量%添加する、請求項1から8までのいずれか1項に記載の方法。
- 工程iii)後に成核剤e2を工程iii)後のポリマー材料に対して0.05〜5.0質量%添加する、請求項1から8までのいずれか1項に記載の方法。
- 工程iii)後に相溶化助剤e3を工程iii)後のポリマー材料に対して0.05〜15.0質量%添加する、請求項1から8までのいずれか1項に記載の方法。
- 工程iv)において鎖長延長剤としてヘキサメチレンジイソシアネート(成分d1)を使用する、請求項1から11までのいずれか1項に記載の方法。
- 請求項5に記載の方法により得られた、脂肪族ジカルボン酸および芳香族ジカルボン酸、および脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステル。
- 請求項5に記載の方法ならびに請求項12記載の鎖長延長により得られた、脂肪族ジカルボン酸および芳香族ジカルボン酸、および脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステル。
- 請求項10に記載の方法により得られた、脂肪族ジカルボン酸および芳香族ジカルボン酸、および脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステル。
- 請求項11に記載の方法により得られた、脂肪族ジカルボン酸および芳香族ジカルボン酸、および脂肪族ジヒドロキシ化合物を基礎とする生分解可能なポリエステル。
- 次のもの:
A)
a1)次のもの:コハク酸、アジピン酸およびセバシン酸からなる群から選択された少なくとも1つの脂肪族ジカルボン酸またはそのエステル、またはその混合物35〜60モル%;
a2)テレフタル酸またはそのエステル、またはその混合物65〜40モル%からなる酸成分、および
この場合成分a1)およびa2)のモル%は、全部で100%であり、および
B)次のもの:
b1)1,4−ブタンジオールまたは1,3−プロパンジオール、またはその混合物からなる群から選択されたジオール成分;
b2)成分AおよびBに対してグリセリン0.05〜1質量%、
D)成分
d1)成分AおよびBに対してヘキサメチレンジイソシアネート0.1〜2質量%;
から形成され、および
1.0mg KOH/g未満のDIN EN 12634により測定された酸価および6cm3/10分未満のISO 1133によるMVR(190℃、質量2.16kg)を有する、請求項1〜12のいずれか1項に記載の方法により得られた生分解可能なポリエステル。 - i)請求項17記載のポリエステル5〜95質量%;
ii)脂肪族ポリエステル、ポリカプロラクトン、澱粉、セルロース、ポリヒドロキシアルカノエート、ポリグリコール酸およびポリ乳酸からなる群から選択された少なくとも1つまたはそれ以上の成分95〜5質量%を含有する生分解可能なポリエステル混合物。 - 生分解可能なポリマー混合物を製造するための請求項16記載のポリエステルの使用。
- 滑剤がエルカ酸アミドまたはステアレートである、請求項9に記載の方法。
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US9040639B2 (en) | 2015-05-26 |
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MX2010011149A (es) | 2010-11-05 |
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CN102007159A (zh) | 2011-04-06 |
US20140128514A1 (en) | 2014-05-08 |
WO2009127556A1 (de) | 2009-10-22 |
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