JP5736303B2 - 脂肪−芳香族生分解性ポリエステル - Google Patents
脂肪−芳香族生分解性ポリエステル Download PDFInfo
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- JP5736303B2 JP5736303B2 JP2011507932A JP2011507932A JP5736303B2 JP 5736303 B2 JP5736303 B2 JP 5736303B2 JP 2011507932 A JP2011507932 A JP 2011507932A JP 2011507932 A JP2011507932 A JP 2011507932A JP 5736303 B2 JP5736303 B2 JP 5736303B2
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- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010902 straw Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- CSKKAINPUYTTRW-UHFFFAOYSA-N tetradecoxycarbonyloxy tetradecyl carbonate Chemical compound CCCCCCCCCCCCCCOC(=O)OOC(=O)OCCCCCCCCCCCCCC CSKKAINPUYTTRW-UHFFFAOYSA-N 0.000 description 1
- 150000003609 titanium compounds Chemical class 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- 239000012745 toughening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 150000003751 zinc Chemical class 0.000 description 1
- 150000003752 zinc compounds Chemical class 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical class [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
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Description
本発明は、前記ポリエステル類と天然または合成のいずれかに由来の他の生分解性ポリマー類とのブレンドにも関する。
エポキシ化されたオイルからの、および/または1,000〜10,000の間の分子量の範囲で、1分子当たり1〜30、好ましくは5〜25の範囲のエポキシド数を有する、スチレン−グリシジルエーテル−メチルメタクリレート、グリシジルエーテルメチルメタクリレートからの全てのポリエポキシド;
ならびにジエチレングリコールジグリシジルエーテル、ポリエチレングリコールジグリシジルエーテル、グリセロールポリグリシジルエーテル、ジグリセロールポリグリシジルエーテル、1,2−エポキシブタン、ポリグリセロールポリグリシジルエーテル、イソプレンジエポキシドおよび脂環式ジエポキシド、1,4−シクロヘキサンジメタノールジグリシジルエーテル、グリシジル2−メチルフェニルエーテル、グリセロールプロポキシレートトリグリシジルエーテル、1,4−ブタンジオールジグリシジルエーテル、ソルビトールポリグリシジルエーテル、グリセロールジグリシジルエーテル、メタ−キシレンジアミンのテトラグリシジルエーテル、ビスフェノールAのジグリシジルエーテルおよびビスフェノールFのジグリシジルエーテル、およびそれらの混合物を含む群から選択されるエポキシドである。
−1方向および2方向に延伸したフィルム、ならびに他のポリマーで多層化したフィルム;
−マルチングで用いるフィルムのような、農業分野で使用するためのフィルム;
−食品用の、農業でのベール梱包用の、および廃棄物包装用のクリングフィルム;
−例えばパレット、ミネラルウォーター、シックスパックリング(six pack rings)等用のようなシュリンクフィルム;
−有機廃棄物の収集、例えば食料廃棄物および園芸廃棄物の収集用のバッグおよびゴミ袋;
−牛乳、ヨーグルト、肉、野菜等用の容器のような、単層および多層両方の熱成形した食品包装材;
−押出コーティング法を用いて得られるコーティング;
−例えば、紙、プラスチック、アルミニウムまたは金属フィルムのような硬質または軟質な基材との多層ラミネート;
−加熱して得られる部材を製造するための発泡または発泡性ビーズ;
−予備発泡品を用いて成形した発泡ブロックを含む、発泡および半発泡製品;
−発泡シート、熱成形した発泡シート、およびそれらから得られる食品包装用の容器;
−一般的な果物および野菜用の容器;
−ゲル化、分解および/または複合化した澱粉;天然の澱粉;小麦粉;天然、植物または無機由来の他の充填剤との複合材料;
−繊維;マイクロ繊維;PLA、PET、PTT等のような硬質なポリマーからなるコアと本発明の材料を用いて製造される外部シェルとを有する複合繊維;ダブレンズの複合繊維(dablens composite fibres);円形からマルチローブ(multilobed)までの異なった断面を有する繊維;フレーク状の繊維;衛生および衛生学上の製品で、ならびに農業および衣服の分野で使用するための、織物および不織布またはスパンボンドした繊維かもしくは熱で結合させた繊維
の製造に好適である。
(例えば、ポリブチレン テレフタレート−コ−セバケート、ポリブチレン テレフタレート−コ−アゼレート、ポリブチレン テレフタレート−コ−ブラシレート、ポリブチレン テレフタレート−コ−アジペート、ポリブチレン テレフタレート−コ−サクシネートおよびポリブチレン テレフタレート−コ−グルタレート等の脂肪/芳香族コポリエステルのような)同じタイプのポリエステルと、
他の生分解性ポリエステル(例えば、ポリ−L−乳酸、ポリ−D−乳酸および立体化学的に複合化させたポリ乳酸;ポリ−ε−カプロラクトン;ポリヒドロキシブチレートバリレート、ポリヒドロキシブチレートプロパノエート、ポリヒドロキシブチレートヘキサノエート、ポリヒドロキシブチレートデカノエート、ポリヒドロキシブチレートドデカノエート、ポリヒドロキシブチレートヘキサデカノエート、ポリヒドロキシブチレートオクタデカノエートのようなポリヒドロキシブチレート;ポリアルキレンサクシネート;ポリ−3−ヒドロキシブチレート;ポリ−4−ヒドロキシブチレート;ポリサクシネートならびに、特にポリブチレンサクシネートおよびアジピン酸および乳酸とのその共重合体)両方との、
またはポリエステル以外のポリマーとの反応性押出によって得ることもできる。ポリエステルとポリ乳酸とのブレンドが特に好ましい。
−8より高い親水性/親油性バランスの指数値(HLB)を有し、ポリオールおよび4.5より低い解離定数pKを有するモノもしくはポリカルボン酸(ポリカルボン酸の場合、前記値は最初のカルボキシ基のpKに関する。)から得られるエステルのような添加剤;
−ポリオール、および12未満の炭素原子を有し、4.5より高いpK値(ポリカルボン酸の場合、前記値は最初のカルボキシ基のpKに関する)を有するモノまたはポリカルボン酸から得られ、5.5〜8の間のHLB値を有するエステル
−ポリオールおよび12〜22の炭素原子を有する脂肪酸から得られ、5.5より低いHLB値を有するエステル
に属することができる。
60%の芳香族単位を有するポリ(ブチレン フランジカルボキシレート−コ−ブチレン セバケート)の合成
次のもの:
2,5−フランジカルボン酸のジメチルエステル(DMFD)
:5.15g(0.0280モル)
セバシン酸 :3.77g(0.0187モル)
1,4−ブタンジオール :5.88g(0.0654モル)
を、シールした機械攪拌機および蒸留液を回収するための目盛り付き試験管につなげた水冷装置を取り付けた100mlの2頚のバルーン(balloon)内に投入した。
バルーンを200℃の温度に温度制御した油浴中に浸漬し、400rpmで継続的に攪拌した。水とメタノールを反応の間に蒸留した。100ppmのテトラオルトブチルチタネート(デュポン社より市販されているタイゾール(商標))をエステル化触媒として加え、油浴の温度を3時間かけて235℃に徐々に加熱した後、蒸留を1時間行った。反応の間に得られる蒸留液の重量と理論収量との間の比として算出される、得られた転化率は約82%であった。
次いで水冷装置を、蒸留液を回収するためのコード化され(coded)、目盛りの付いた試験管を取り付けた空冷装置に替え、重縮合触媒としてさらに1000ppmのタイゾール(商標)を加えた。圧力を約10分間かけて1mbarに下げた。油の温度を240℃まで上げ、反応を2時間さらに行った。ASTM標準D2857−89に従って、クロロホルム中、25℃で測定した(2g/l)、1.06dl/gに等しい固有粘度を有する生成物を得た。
Tm=104℃、Tc=39℃、
ΔHf=19.0J/g、
ΔHc=−13.6J/g、
Tg=−18℃
を得た。
GPCのトレース:Mn=68,784、Mw=129,690、Mz=226,090、Mw/Mn=1.8854。
引張応力下での機械的特性:
降伏応力(MPa) 5.5
極限荷重(MPa) 33.5
降伏伸び(%) 30
極限伸び(%) 950
弾性率(MPa) 65
極限エネルギー(MJ/m3) 165
引裂抵抗
エルメンドルフ(N/mm) >65
70%の芳香族単位を有するポリ(ブチレン フランジカルボキシレート−コ−ブチレン セバケート)の合成
実施例1の方法を、次の組成:
2,5−フランジカルボン酸のジメチルエステル(DMFD)
:16.24g(0.0883モル)
セバシン酸 : 7.64g(0.0378モル)
1,4−ブタンジオール :15.63g(0.177モル)
で繰り返した。
Tm=122.1℃、Tc=60.6℃、
ΔHf=19.8J/g、
ΔHc=−18.6J/g、
Tg=−13℃
を得た。
GPCのトレース:Mn=45,125、Mw=88,995、Mz=152,373、Mw/Mn=1.9722。
引張応力下の機械的特性:
降伏応力(MPa) 8.9
極限荷重(MPa) 32.5
降伏伸び(%) 28
極限伸び(%) 520
弾性率(MPa) 110
極限エネルギー(MJ/m3) 115
引裂抵抗
エルメンドルフ(N/mm) >50
実施例1のポリマー63重量部を、(130,000のMn、3.5g/10分のMFR(190℃;2.16kg)、0.2%未満の残存ラクチドおよび約6%のD体量を有する)ポリL−ラクチドポリマー5重量部、澱粉23.5重量部、水3.5重量部およびグリセロール5重量部とブレンドした。使用した押出機は2軸の押出機(ハアケ レオコード90レオメックス(Haake Rheocord 90 Rheomex) TW−100)であった。熱のプロフィルは120〜190℃の間の範囲であった。顆粒の最終的な含水量は0.8%に等しかった。
実施例1のポリマー80重量部を、(130,000のMn、3.5g/10分のMFR(190℃;2.16kg)、0.2%未満の残存ラクチドおよび約6%のD体量を有する)ポリL−ラクチドポリマー20重量部とブレンドした。使用した押出機は2軸の押出機(ハアケ レオコード90レオメックス TW−100)であった。熱のプロフィルは120〜190℃の間の範囲であった。顆粒の最終的な含水量は0.8%に等しかった。
実施例1のポリマー70重量部を、澱粉27重量部および水2.4重量部とブレンドした。使用した押出機は2軸の押出機(ハアケ レオコード90レオメックス TW−100)であった。熱のプロフィルは120〜190℃の間の範囲であった。顆粒の最終的な含水量は0.8%に等しかった。
表2の生成物について、生分解性試験をISO標準14855−改定1に従って制御した堆肥中で行った。液体窒素中で粉砕したペレットが250μmより小さい粒子径を有する粒子に分解されるまで、前記ペレットを試験した。カラムクロマトグラフィ用の正に制御した微結晶セルロース アヴィセル(Avicel)(R)として、lot No.K29865731 202を用いた。
粉末の粒度:20μm〜160μmの間が80%であり、20μm未満が20%である。
Claims (11)
- 脂肪族ジカルボン酸、ジオールおよび多官能性芳香族酸から得られ、該芳香族酸が再生可能資源由来のジカルボン酸であることを特徴とする脂肪−芳香族タイプの生分解性ポリエステルであって、
前記再生資源由来のジカルボン酸が2,5−フランジカルボン酸およびその誘導体から選択され、前記再生資源由来のジカルボン酸の含有量が20〜70モル%であること、および前記生分解性ポリエステルが、前記脂肪族ジカルボン酸全量の0〜30モル%の量の少なくとも1つのヒドロキシ酸を含むことを特徴とし、
前記脂肪族ジカルボン酸がアジピン酸ならびにC 8 〜C 13 のタイプの再生可能資源由来のジカルボン酸およびそれらのエステルから選択され、
前記生分解性ポリエステルの分子量M n が20,000〜100,000の間であり、
多分散性指数M w /M n が1.6〜5の間である、生分解性ポリエステル。 - 再生可能資源由来の脂肪族ジカルボン酸が、アゼライン酸、セバシン酸、スベリン酸、ブラシル酸およびそれらのエステルから選択される、請求項1に記載の生分解性ポリエステル。
- ジオールが、1,2−エタンジオール、1,2−プロパンジオール、1,3−プロパンジオール、1,4−ブタンジオール、1,5−ペンタンジオール、1,6−ヘキサンジオール、1,7−ヘプタンジオール、1,8−オクタンジオール、1,9−ノナンジオール、1,10−デカンジオール、1,11−ウンデカンジオール、1,12−ドデカンジオール、1,13−トリデカンジオール、1,4−シクロヘキサンジメタノール、プロピレングリコール、ネオペンチルグリコール、2−メチル−1,3−プロパンジオール、ジアンヒドロソルビトール、ジアンヒドロマンニトール、ジアンヒドロイジトール、芳香族ジオールおよびフランジオールである、請求項1又は2に記載の生分解性ポリエステル。
- ジオールがC2〜C10のタイプである、請求項3に記載の生分解性ポリエステル。
- 請求項1〜4のいずれか一つに記載の生分解性ポリエステルおよび天然または合成いずれかに由来の他の生分解性ポリマーを含むブレンド。
- 合成由来のポリマーが、脂肪/芳香族コポリエステル;ポリ−L−乳酸、ポリ−D−乳酸および立体化学的に複合化させたポリ乳酸;ポリ−ε−カプロラクトン;ポリヒドロキシブチレートバリレート、ポリヒドロキシブチレートプロパノエート、ポリヒドロキシブチレートヘキサノエート、ポリヒドロキシブチレートデカノエート、ポリヒドロキシブチレートドデカノエート、ポリヒドロキシブチレートヘキサデカノエート、ポリヒドロキシブチレートオクタデカノエートのようなポリヒドロキシブチレート;ポリアルキレンサクシネート;ポリ−3−ヒドロキシブチレート;ポリ−4−ヒドロキシブチレート;ポリサクシネートならびに、特にポリブチレンサクシネートおよびアジピン酸および乳酸とのそのコポリマーから選択される生分解性ポリエステルである、請求項5に記載のブレンド。
- 天然由来のポリマーが、澱粉、セルロース、キチンおよびキトサン、アルギネート、グルテンのような蛋白質、ゼイン、カゼイン、コラーゲン、ゼラチン、天然ゴム、ロジン酸およびその誘導体、リグニンおよびそれらの誘導体から選択される、請求項5に記載のブレンド。
- 澱粉が分解もしくはゲル化したいずれかの形態で、または充填剤として加えられる、請求項7に記載のブレンド。
- 澱粉が連続もしくは分散相を示し、または共連続的な形態である、請求項8に記載のブレンド。
- 合成由来のポリマーがポリ乳酸であり、天然由来のポリマーが澱粉である、請求項6に記載のブレンド。
- −1方向および2方向に延伸したフィルム、ならびに他のポリマーで多層化したフィルム;
−マルチングで用いるフィルムのような、農業分野で使用するためのフィルム;
−食品用の、農業でのベール梱包用の、および廃棄物包装用のクリングフィルム;
−有機廃棄物の収集、例えば食料廃棄物および園芸廃棄物の収集用のバッグおよびゴミ袋;
−牛乳、ヨーグルト、肉、野菜等用の容器のような、単層および多層両方の熱成形した食品包装材;
−押出コーティング法を用いて得られるコーティング;
−紙、プラスチック、アルミニウムまたは金属フィルムの層との多層ラミネート;
−加熱して得られる部材を製造するための発泡または発泡性ビーズ;
−予備発泡品を用いて成形した発泡ブロックを含む、発泡および半発泡製品;
−発泡シート、熱硬化性発泡シート、およびそれらから得られる食品包装用の容器;
−一般的な果物および野菜用の容器;
−ゲル化、分解および/または複合化した澱粉、天然の澱粉、小麦粉、または植物もしくは無機の天然の充填剤との複合材料;
−衛生および衛生学上の製品中で、ならびに農業および衣服の分野で使用するための、繊維、織物および不織布
を製造するための、請求項1〜10のいずれか一つに記載のポリエステルの使用。
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IT000840 IT1387503B (it) | 2008-05-08 | 2008-05-08 | Poliestere biodegradabile alifatico-aromatico |
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US11345779B2 (en) | 2022-05-31 |
MX2010012102A (es) | 2010-11-30 |
PL2276789T5 (pl) | 2018-12-31 |
CA2721699A1 (en) | 2009-11-12 |
ES2511915T5 (es) | 2018-11-19 |
KR101626997B1 (ko) | 2016-06-03 |
US10526442B2 (en) | 2020-01-07 |
US20160200862A1 (en) | 2016-07-14 |
IT1387503B (it) | 2011-04-13 |
EP2276789B2 (en) | 2018-07-18 |
CA2721699C (en) | 2017-03-28 |
US20110071238A1 (en) | 2011-03-24 |
US10316139B2 (en) | 2019-06-11 |
PL2276789T3 (pl) | 2015-02-27 |
CN102027037A (zh) | 2011-04-20 |
EP2276789A1 (en) | 2011-01-26 |
ES2511915T3 (es) | 2014-10-23 |
US20200079899A1 (en) | 2020-03-12 |
KR20110008318A (ko) | 2011-01-26 |
BRPI0908672A2 (pt) | 2017-07-18 |
WO2009135921A1 (en) | 2009-11-12 |
ITMI20080840A1 (it) | 2009-11-09 |
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