JP4806794B2 - ポリエステル包装材料中における有機物質濃度の置換シクロデキストリン化合物による低下 - Google Patents
ポリエステル包装材料中における有機物質濃度の置換シクロデキストリン化合物による低下 Download PDFInfo
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Description
飲料製造業者は、長い間、改良バリア物質を求めてきた。この研究努力は、大部分が、二酸化炭素(CO2)バリア、酸素(O2)バリアおよび蒸気(H2O)バリアに関していた。さらに最近になって、もともとボトル製造に携わってきた業者達は、前記樹脂または容器中に飲料に抽出可能かまたは飲料に溶解する物質の存在に対する感度を有意に高めてきた。この研究は、バルクプラチックを透過性の低いポリマーのポリマーコーティングまたは積層体によって改良し透過性を低下させるためであった。しかし、我々は、飲料容器のバルクポリマーレジンまたはポリエステル物質中に、プリフォーム製造プロセス中にポリエステル樹脂に含まれた金属触媒残渣を捕捉し、前記樹脂または容器中の触媒残渣が原因の触媒により発生した飲料抽出可能なまたは飲料溶解可能な物質を低下させる活性錯化化合物を導入することには思い至らなかった。
ポリエステル樹脂の安定化およびアセトアルデヒドのような反応性有機物の吸収は、かなりの注目を集めてきていた。この問題を解決する提案が提起されてきた。ひとつの提案は、WO 9744376、EP26713および米国特許第5,874,517号およびJP 57049620に示されているように、リン化合物および窒素複素環を含む活性安定化剤を用いることを必要としている。非常に注目された別の提案では、固体状態重縮合(SSP)プロセッシングを含んでいる。前記2回目の重合段階後の物質を水または脂肪族アルコールで処理して、分解により残留物を低下させる。最後に、アセトアルデヒドを、キシリレンジアミン物質および低分子量芳香族ポリアミドに基づく低分子量部分芳香族ポリアミド反応性化学物質によって捕捉できる。[米国特許第5,258,233号、6,042,908号および欧州特許0 714 832を参照、市販ポリアミドについてはWO9701427を参照、ポリエチレンイミンについては5,362784を参照、テレフタル酸のポリアミドについては、WO9728218を参照、およびゼオライトのような無機吸収剤の用途については、米国特許第4,391,971号を参照。]
本発明の熱可塑性物質は、好適には一級炭素原子上に1置換基を有するシクロデキストリンを含むことができるシクロデキストリン化合物を含有する。このようなシクロデキストリン物質は、捕捉およびバリア性において熱可塑性ポリエステル物質に相溶性であることが明らかとされている。前記シクロデキストリン物質を熱可塑体に添加し、溶融処理時において、プリフォームおよび最終飲料容器中に捕捉性質およびバリア性を付与する。前記シクロデキストリン物質は時間、温度の良好な製造条件下で、相溶性で、燃焼せず、最終容器中ポリマー外観において曇または構造性の低下または透明性低下を生ずることがない。
水溶液は、吸収剤1キログラム当たり約10乃至350リットルの速度で前記活性炭吸収剤または樹脂吸着剤に接触させることができる。前記溶液が前記吸収剤と接触する滞留時間を調整し、実質的に不純物を除去できるようにする。しかし、前記溶液は、一般に、約0.5乃至24時間前記吸収剤と接触するように保持される。
図1は、種々のシクロデキストリン分子の大きさを概念的に示した一般的な等尺性図面である。図1は、α、β、またはγ−シクロデキストリンを示し、シクロデキストリン環の外部の大きさと透過物またはポリマー不純物のトラップ部位として作用できる内孔の大きさを示している。図1は、一級およびニ級水酸基が環状形態の端に存在することを示している。
図2は、実質的に透明な容量2リットルの炭酸飲料容器の側面図である。全体を20で示した前記容器は、本体22、土台24およびフタ部分26を含む。前記容器の全形状が、熱可塑吹込成形操作により形成される。土台24は、ボトル製造時に形成された自己支持性土台である。このようなボトルは、パリソン形成時に形成されたもうひとつの熱可塑性物質を有するパリソンから調製された第2層17を有するかまたは液体コーティング物質に由来する第2層17を有することができる。液体コーティング物質は、パリソンコーティングまたはボトルコーティングのいずれかである。
図3−7は、下記の実験の章で検討する。
これまでの説明は、前記適用の種々の態様および本発明の物質のアセトアルデヒド低下およびバリアおよび錯体化性質を示している。下記の実施例および
データはさらに、本発明を例示し、最良の形態を含んでいる。
固有粘度(IV)は、一般的無晶性ポリマー組成物0.2グラムをジクロロ酢酸20ミリリットルと温度25℃で混合し、その相対的粘度(RV)をUbbelhode粘度計を用いて決定する。RVは、式IV=[(RV−1)×0.691]+0.063を用いてIVに変換する。ポリマーチップの色は、Minolta Chroma−meter CR−310分光光度計を用いてASTM D6290−98を用いて測定し、1個以上のCIE L*、a*およびb*標準単位として報告した。プリフォームの曇りは、また、この機器を用いて測定した。
アセトアルデヒドは、本発明の望ましくない有機化合物阻害性質にとって良好なモデルである。表1は、重縮合物無晶ポリエチレンテレフタレート中におけるアセトアルデヒド(AA)低下を示し分析試験結果を含んでいる(実施例1−21)。Wacker Biochem Corporation製造のさまざまなシクロデキストリン化合物(未修飾および修飾)を、溶融重縮合ポリエチレンテレフタレート中に溶融PETをバッチ反応容器から押し出す2分前に添加し、冷水でクエンチさせ、ペレットとしてチップ化した(チップとも称される)。この試験は、アセトアルデヒド除去についてさまざまなシクロデキストリンを評価するために行った。溶融レジン押し出し前のこの特定バッチプロセスにおけるアセトアルデヒド濃度バランスは、約60ppmである。シクロデキストリン化合物は、前記プロセスの最後の2分間に添加させ、反応容器ミキサーにより分散される。2分後、ポリエチレンテレフタレートを前記ミキサーから押し出す。バッチ反応容器からクエンチ水中に出る溶融レジンの流れは、ヌードルと称される。前記反応容器から溶融レジンを水切りするため、数分が必要である。前記ヌードルサンプルを極低温的に冷却し、10メッシュまたはそれより細かく粉砕し、ガラスサンプル瓶に入れ、すぐに密封する。顆粒化PETサンプル0.25+/−0.002gを22mlのガラスバイアルに入れる。このバイアルを、テフロン表面のブチルゴム隔壁およびアルミニウムクリンプトップを用いてすぐにふたをする。バイアルを90分間160℃に加熱することによって前記上部空間にサンプルからアセトアルデヒドを脱着し、ついで、静止上部空間ガスクロマトグラフィによってフレームイオン化検出を用いてアセトアルデヒドについて分析する。0.05wt%および0.10wt%の未修飾β―シクロデキストリン化合物を有する物質は、全ヌードル押し出し物について透明であった。
プリフォームデータは、表17に要約してある。
Claims (13)
- ポリエステルチップを製造する方法であって、
(a)溶融ポリエステルを含むストリームを出口オリフィスを有するプロセスデバイスを通過させることと、
(b)置換シクロデキストリン化合物を含む液体を形成させることと、
(c)前記置換シクロデキストリン化合物を含む液体を、前記プロセスデバイス中の混合手段の近くで溶融ポリエステルのストリーム中に導入することと、
(d)前記置換シクロデキストリン化合物を含む液体と前記溶融ポリエステルとを前記混合手段で混合して処理ストリームを形成することと、
(e)前記処理ストリームを前記オリフィスを通過させ、前記ポリエステルチップを形成させることと、
から成る方法。 - 前記液体が、置換シクロデキストリン化合物を1.0乃至50重量パーセント含む請求項1記載の方法。
- 前記液体が、溶融ポリエチレンテレフタレートを含みかつ前記混合手段が前記オリフィス近位である請求項1記載の方法。
- 前記混合手段が次に前記オリフィスに隣接している請求項1記載の方法。
- 前記液体がオイルを含む請求項1記載の方法。
- 前記ポリエステルが、少なくとも60重量%のポリエチレンテレフタレート単位を含む請求項1記載の方法。
- 前記ポリエステルが、少なくとも60重量%のポリエチレンナフタレート単位を含む請求項1記載の方法。
- 前記シクロデキストリン化合物が、シクロデキストリン中グルコースの6位において少なくとも1個の−OH基上に置換基を有する請求項1記載の方法。
- 前記シクロデキストリン化合物が6−O−メチルエーテルを含む請求項1記載の方法。
- 前記シクロデキストリン化合物が6−Oアセチルエステルを含む請求項1記載の方法。
- 前記置換シクロデキストリン化合物が、ポリエステルレジン100万部当たり350重量部乃至900重量部の量で0.5乃至1.2の置換度を含む請求項1記載の方法。
- 前記液体が、粉末化シクロデキストリン化合物を押し出し機デバイス中で溶融ポリエステルストリーム中に導入されることによって形成される請求項3記載の方法。
- 前記チップが、チップ形成後SSPプロセッシングに供される請求項1記載の方法。
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Application Number | Priority Date | Filing Date | Title |
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US10/163,817 US6709746B2 (en) | 2002-06-05 | 2002-06-05 | Reducing concentration of organic materials with substituted cyclodextrin compound in polyester packaging materials |
US10/163,817 | 2002-06-05 |
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JP2004511374A Division JP4264062B2 (ja) | 2002-06-05 | 2002-12-09 | ポリエステル包装材料中における有機物質濃度の置換シクロデキストリン化合物による低下 |
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JP2008239991A JP2008239991A (ja) | 2008-10-09 |
JP4806794B2 true JP4806794B2 (ja) | 2011-11-02 |
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JP2008085760A Expired - Fee Related JP4806794B2 (ja) | 2002-06-05 | 2008-03-28 | ポリエステル包装材料中における有機物質濃度の置換シクロデキストリン化合物による低下 |
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EP (1) | EP1513887B8 (ja) |
JP (2) | JP4264062B2 (ja) |
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CN (1) | CN100569836C (ja) |
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AU (1) | AU2002362111A1 (ja) |
CA (1) | CA2487437C (ja) |
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2002
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- 2002-12-09 JP JP2004511374A patent/JP4264062B2/ja not_active Expired - Fee Related
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- 2002-12-09 WO PCT/US2002/039346 patent/WO2003104308A1/en active Application Filing
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Also Published As
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US20040161602A1 (en) | 2004-08-19 |
US6709746B2 (en) | 2004-03-23 |
DE60229171D1 (de) | 2008-11-13 |
US6878457B2 (en) | 2005-04-12 |
KR100943925B1 (ko) | 2010-02-24 |
EP1513887B1 (en) | 2008-10-01 |
JP2008239991A (ja) | 2008-10-09 |
US20030232208A1 (en) | 2003-12-18 |
JP4264062B2 (ja) | 2009-05-13 |
AU2002362111A1 (en) | 2003-12-22 |
CA2487437C (en) | 2010-11-02 |
AU2002362111A8 (en) | 2003-12-22 |
CN100569836C (zh) | 2009-12-16 |
CN1628143A (zh) | 2005-06-15 |
CA2487437A1 (en) | 2003-12-18 |
WO2003104308A1 (en) | 2003-12-18 |
JP2005528514A (ja) | 2005-09-22 |
US6974603B2 (en) | 2005-12-13 |
US20040151856A1 (en) | 2004-08-05 |
KR20050043798A (ko) | 2005-05-11 |
ES2310619T3 (es) | 2009-01-16 |
HK1077314A1 (en) | 2006-02-10 |
MXPA04012017A (es) | 2005-10-05 |
US20050182234A1 (en) | 2005-08-18 |
EP1513887A1 (en) | 2005-03-16 |
US7018712B2 (en) | 2006-03-28 |
ATE409718T1 (de) | 2008-10-15 |
EP1513887B8 (en) | 2008-11-19 |
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