JP5933158B2 - 固相重合を行わないポリエステルバリア樹脂の製造方法、その方法により製造されたコ−ポリエステル樹脂、およびそのコ−ポリエステル樹脂から製造された透明単層容器 - Google Patents
固相重合を行わないポリエステルバリア樹脂の製造方法、その方法により製造されたコ−ポリエステル樹脂、およびそのコ−ポリエステル樹脂から製造された透明単層容器 Download PDFInfo
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- JP5933158B2 JP5933158B2 JP2008544429A JP2008544429A JP5933158B2 JP 5933158 B2 JP5933158 B2 JP 5933158B2 JP 2008544429 A JP2008544429 A JP 2008544429A JP 2008544429 A JP2008544429 A JP 2008544429A JP 5933158 B2 JP5933158 B2 JP 5933158B2
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- YYYYLWPWZWOIMP-UHFFFAOYSA-L [Na+].[Na+].OP(O)=O.[O-]P([O-])=O Chemical compound [Na+].[Na+].OP(O)=O.[O-]P([O-])=O YYYYLWPWZWOIMP-UHFFFAOYSA-L 0.000 description 1
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- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000002178 crystalline material Substances 0.000 description 1
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- 239000012975 dibutyltin dilaurate Substances 0.000 description 1
- VILAVOFMIJHSJA-UHFFFAOYSA-N dicarbon monoxide Chemical compound [C]=C=O VILAVOFMIJHSJA-UHFFFAOYSA-N 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 125000006182 dimethyl benzyl group Chemical group 0.000 description 1
- GYUVMLBYMPKZAZ-UHFFFAOYSA-N dimethyl naphthalene-2,6-dicarboxylate Chemical compound C1=C(C(=O)OC)C=CC2=CC(C(=O)OC)=CC=C21 GYUVMLBYMPKZAZ-UHFFFAOYSA-N 0.000 description 1
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- 230000009977 dual effect Effects 0.000 description 1
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- QVTWBMUAJHVAIJ-UHFFFAOYSA-N hexane-1,4-diol Chemical compound CCC(O)CCCO QVTWBMUAJHVAIJ-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
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- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 239000002114 nanocomposite Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000002055 nanoplate Substances 0.000 description 1
- 239000003345 natural gas Substances 0.000 description 1
- 239000002667 nucleating agent Substances 0.000 description 1
- 238000010525 oxidative degradation reaction Methods 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000012466 permeate Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- IYDGMDWEHDFVQI-UHFFFAOYSA-N phosphoric acid;trioxotungsten Chemical compound O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.O=[W](=O)=O.OP(O)(O)=O IYDGMDWEHDFVQI-UHFFFAOYSA-N 0.000 description 1
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- 238000004611 spectroscopical analysis Methods 0.000 description 1
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- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
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- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000005979 thermal decomposition reaction Methods 0.000 description 1
- 239000012815 thermoplastic material Substances 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 238000012546 transfer Methods 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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Images
Classifications
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- B29C51/00—Shaping by thermoforming, i.e. shaping sheets or sheet like preforms after heating, e.g. shaping sheets in matched moulds or by deep-drawing; Apparatus therefor
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- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
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Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Polyesters Or Polycarbonates (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Containers Having Bodies Formed In One Piece (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Blow-Moulding Or Thermoforming Of Plastics Or The Like (AREA)
- Polyamides (AREA)
Description
−分子内フェニル環の、ポリエステル鎖に沿った急な動き、
−二軸延伸後の高分子鎖の整列、
−有機重合体または特殊な樹脂の自由体積画分、および
−重合体ブレンドの有効自由体積
が挙げられる。
1.FTIRによる、炭酸入りビンのCO2損失速度、
2.透過電子顕微鏡(TEM)による、マトリックスおよび共−バリア領域、
3.陽電子線による、有機重合体の自由体積微小構造、
4.CO2または空気を満たしたチャンバー内における、炭酸を入れていないビンの直接CO2またはO2流入速度(マイクロリットル/包装物/日)、
5.二重体積収着セルにおける圧力減衰によるガス収着を経由するフィルム(または薄いシート)の透過性(例えば、「圧力減衰により重合体におけるガス収着を測定するための設計要件」(Design Considerations for Measurement ofGas Sorption in Polymers by Pressure Decay)、W.J. KorosおよびD.R. Paul, J. Polym. Sci.-Polymer Physics Edition, 14, 1903-1907, 1976(この文献は引用されることにより本明細書の開示の一部とされる。))、および
6.エレクトロバランスによる、ガス収着を経由するフィルム(または薄いシート)の透過性
を挙げることができる。
例1〜3に規定する標準PET樹脂を、射出成形前に、水分50ppmに乾燥させ、24-gプリフォームに成形し、次いでこれを側壁の厚さが約10〜12ミルである20 oz.の直線壁ビンにブロー成形した。射出成形条件は、穏やかな条件下で、透明で無応力のプリフォームを製造するように、最適化した。これらのプリフォームを、材料が適切に配分された良好な透明ビン(応力による白化およびヘーズが無い)を製造する条件下でブロー成形した。ビンは、僅かなパール(pearl)上2%でブロー成形した。
TPA 総ジ酸の97%
IPA 総ジ酸の3%
EG
DEG
標準添加剤(Co、P、Sb)
元素状コバルト25 ppm(酢酸コバルト四水和物106 ppm)
TPA 総ジ酸の97%
IPA 総ジ酸の3%
EG
DEG
標準添加剤(Co、P、Sb)
元素状コバルト80〜100 ppm(酢酸コバルト四水和物338〜410 ppm)
TPA 総ジ酸の97%
IPA 総ジ酸の3%
EG
DEG
標準添加剤(P、Sb、有機トナー)
y=1.58(%損失/週)x+2.02
として求めた。
非延伸PETおよび非延伸MXD6は、屈折率が全ての方向(x、yおよびZ)で約1.58である。二軸延伸の後、PETおよびMXD6は、異なった屈折率値を有する。PETの屈折率は、平面延伸比10〜16全体にわたって、x、y方向で、MXD6より高い。他方、MXD6は、平面延伸比10〜16全体にわたって、Z方向でPETより高い屈折率を有する。従って、PETの配向度(nx+ny)/2−nzは、平面延伸比10〜16全体にわたって、MXD6より約4〜5倍高い。標準的なペットボトルでは、軸方向延伸比(2〜3)は、ビンの長さ/プリフォーム長さ(延伸部のみ)として規定され、ループ延伸比(3〜5)は、ビン直径/プリフォーム内径として規定される。得られる平面延伸比は、約12〜14である。炭酸入り清涼飲料(CSD)におけるビンの延伸比は、高温充填用途におけるよりも僅かに高い。成形により導入された(molded-in)応力および最大ひずみ硬化は、容器の性能を改良する。
例4では、MXD6(6001)ペレット(SSP無し)をMitsubishi Gas Chemicalから入手し、共−バリアとして使用した。
マトリックス樹脂:PETドメイン
TPA 総ジ酸の95%
IPA 総ジ酸の4〜5%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
共−バリア:6001ドメイン PETドメインに対して3重量%または5重量%
PET/6001(95/5)ブレンドビン(24 g/20 oz.)
y=0.92(%損失/週)x+2.12
貯蔵寿命17.5%CO2損失で16.7週
例1〜3のPET組成物のCO2損失速度より1.72倍優れたCO2バリア
PET/6001(97/3)ブレンドビン(24 g/20 oz.)
y=1.11(%損失/週)x+2.00
貯蔵寿命17.5%CO2損失で14週
例1〜3のPET組成物のCO2損失速度より1.42倍優れたCO2バリア
PET/6001(97/3)ブレンドビン(28 g/20 oz.)
y=0.87(%損失/週)x+2.38
貯蔵寿命17.5%CO2損失で17.4週
例1〜3のPET組成物のCO2損失速度より1.82倍優れたCO2バリア
例5では、MX-IPA顆粒を、6-gal反応器で製造した。6-gal反応容器中に、MXD6 4.937 kg、アジピン酸4.238 kg(酸成分の80モル%)、IPA 1.208 kg(酸成分の20モル%)、Irganox B 1171 13.6 g(純粋樹脂に対して0.15重量%)を装填した。有機青色トナー9 mg(純粋樹脂に対して1 ppm)および有機赤色トナー4.5mg(純粋樹脂に対して0.5 ppm)を添加し、色bの値を下げることができる。反応混合物を加熱する前に、反応器から空気を排除した。反応は、窒素雰囲気中で行った。反応混合物を195℃に加熱し、アジピン酸を160℃で一様に融解させた。次いで、攪拌機を始動させた。反応混合物の温度を連続的に238℃に上昇させ、反応をさらに1〜3時間続行させた。このバッチの最後に、溶融した材料を水中で急冷した。
マトリックス樹脂:PETドメイン
TPA 総ジ酸の95%
IPA 総ジ酸の4〜5%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
共−バリア:MX-IPAドメイン PETドメインに対して3重量%または5重量%
別の共−バリア樹脂を、例5と同じ反応器中にMXDA 4.977 kg(36.6モル)、アジピン酸4.807 kg(32.9モル)(酸成分の90モル%)、IPA 0.610 kg(3.7モル)(酸成分の10モル%)、およびIrganox B 1171 13.6gを装填して製造した。反応混合物を加熱する前に、反応器から空気を排除した。反応は、窒素雰囲気中で行った。反応混合物を195℃に加熱し、アジピン酸を160℃で一様に融解させた。次いで、攪拌機を始動させた。反応混合物の温度を連続的に238℃に上昇させ、反応をさらに1〜3時間続行させた。このバッチの最後に、溶融した材料を水中で急冷した。
例6の処方を、より大きな反応器中でスケールアップした。175-gal反応容器中に、MXDA 153.2 lb(69.522 kgまたは511モル)、アジピン酸148 lb(67.192 kgまたは460モル)(酸成分の90モル%)、IPA 18.6 lb(8.444 kgまたは51モル)(酸成分の10モル%)、およびIrganox B 1171 200グラム(純粋樹脂に対して0.15重量%)を装填した。アジピン酸とイソフタル酸の両方を最初に反応器中に供給した。ジ酸混合物を加熱する前に、反応器から空気を排除した。反応は、窒素雰囲気中で行った。反応混合物を195℃に加熱し、アジピン酸を160℃で一様に融解させた。次いで、攪拌機を始動させた。次いで、液体MXDAモノマーをジ酸混合物中に連続的に低速度で加えた。MXDAを加えている間、反応温度を連続的に238℃に上昇させ、MXDAを加え終わった後、反応をさらに1〜3時間続行させた。このバッチの最後に、反応器の底部にある排出バルブを開き、粒子を形成した(造粒またはペレット化)。
高IPAチップを、連続式溶融相エステル化/重縮合製法で製造することができる。溶融材料のIVは、用途に応じて、0.5〜0.6でよいか、または溶融樹脂を連続的に目標とするIV0.70〜0.90以上に上げる。樹脂の高温切断および結晶化は、一つ以上の工程で完了させることができる。あるいは、ストランドを低温で湿潤切断し、続いて外部の結晶化装置にかけることもできる。サイロの前に製品冷却装置を使用した。10〜30モル%のIPAを含むHi-IPA樹脂を、このようにして、70〜90モル%IPAで取り扱うことができる。
IPA変性したPET樹脂には、ブロー成形ビンで優れた透明性を有するという利点がある。特定レベルのバリア改良ファクター(BIF)を達成するには、遙かに高いIPA含有量が必要である。商業的な固相重縮合(SSP)製造装置では、結晶化されたチップの分子量または固有粘度(IV)を、一般的に重力流動反応器中で改良する。チップが5%までのIPAを含む場合、特定の温度および処理量で、粘着の問題はほとんど見られない。
TPA 総ジ酸の80〜90%
IPA 総ジ酸の10〜20%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 所望により総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
核形成剤 PEN/PTT、MXD6、MX-IPA、等
経験から、有機変性されたクレーナノ小板は、PETマトリックス中で容易に剥離しないことが分かっている。しかし、これらの有機クレーナノ小板は、MXD6またはMX-IPA(IPA変性されたMXD6)マトリックス中で効果的な分散を示す。そのため、得られるナノ複合材料は、PETマトリックス中で共−バリアとして使用される。MXD6樹脂は、Mitsubishi Gas Chemicalから三種類の製品等級(6001、6007、および6121)で市販されている。溶融粘度は、特定温度で、6001(最低)から6121(最高)に増加する。これらの三等級は全て、温度250〜290℃で処理することができる。Southern Clay Products, Inc.は、Cloisite(登録商標)有機クレーを販売している。二種類のCloisite(登録商標)有機クレー(30B & 93A)を6007ペレットと、共回転二軸スクリュー押出機(1インチ、ZE25、40 L/D、スクリュー#850-1)で混合し、再ペレット化した。
マトリックス樹脂:PETドメイン
TPA 総ジ酸の95%
IPA 総ジ酸の4〜5%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
共−バリア:DAK-9ドメイン PETドメインに対して5重量%
マトリックス樹脂:PETドメイン
TPA 総ジ酸の95%
IPA 総ジ酸の5%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
共−バリア:PEN/PTT PETドメインに対して5重量%/5重量%
マトリックス樹脂:PETドメイン
TPA 総ジ酸の90%
IPA 総ジ酸の9〜10%
5-Na+SO3−-IPAまたは5-Li+SO3−-IPA 総ジ酸の0〜1%
EG
DEG
標準添加剤 (Co、P、Sb)
共−バリア:MX-IPAドメイン PETドメインに対して5重量%
高バリアポリエステル、例えばPGA、PTN、PEI、PEN、等は、溶融状態において、PETによる急速なエステル交換反応を受ける傾向がある。鎖構造が大きく変化するために、ガズバリア特性がある程度改良されることがある。少量のMXDAによる変性で、得られるアミド官能化されたPET鎖が、ある種の独特な利点、例えばより優れた鎖構造、配向後のより近い鎖整列、より低い自由体積、等を示す。典型的なMXDA変性されたポリエステルとしては、MXDA変性されたポリグリコール酸(PGA)、MXDA変性されたPTN、MXDA変性されたPEI、MXDA変性されたPEN等、が挙げられる。ある種のMXDAで構築されたPET(MXDA変性されたPET)鎖は、一つの重合体相を有し、得られるビンは、ヘーズが無く、透明である。MXDA変性されたPETは、PET/共−バリアブレンドよりも、優れたCO2バリアを与えることがあり、PET/共−バリアブレンドは、二つの重合体相(PET中で剥離された共−バリア)を有し、透明な分子的に秩序付けられた材料中で光の複屈折(二重屈折)を示すことが多い。MXDA変性されたPETに関しては例12を参照。
別のバリア樹脂(F-N、MXDA変性されたPET)を15-gar反応器中で製造した。初期攪拌速度は52 rpmに設定した。反応容器に、MXDA 2.27 kg、EG 17.1 kg、TPA 37 kg、IPA 1.15 kg を装填した。標準PET添加剤は、元素状アンチモン219 ppm、元素状コバルト29 ppm、元素状リン29 ppm、およびカーボンブラック0.62 ppmを包含する。窒素掃気後、反応器を窒素で276 kPa(40 psi)に加圧した。初期スラリー温度は110℃であった。溶融温度設定点を260℃に調節した。圧力エステル化を260℃で200〜250分間続けた。反応器を、毎分55 kPaの速度で大気圧に通気した。溶融温度設定点を263℃に増加した。大気圧エステル化を263℃で約1時間続けた。リン酸を装填し、EGを追加して重縮合を開始した。溶融温度設定点を274℃に増加し、反応器圧力を大気圧から700 mmHgに低下させた。毎分25 mmHgの速度で圧力を再度75 mmHgに低下させた。溶融温度設定点を279℃に増加した。反応器圧力が75 mmHgになった後、直ちに、圧力を1 mmHg未満に徐々に下げた。溶融温度設定点を285℃に増加した。重縮合反応が進行するにつれて、攪拌速度を45 rpm、40 rpm、および35 rpmに下げた。熱移動装置を手動式温度制御に設定した。攪拌速度を再び、最終トルク1,600 in-lbfになるまで30 rpm、25 rpm、および20 rpmに下げた。重縮合を、274〜285℃で150〜180分間続けた。次いで、攪拌速度を最低速度に下げた。窒素で真空を緩和し、製品の押出を開始した。圧力エステル化の間、溶融物は透明であり、得られたペレットは透明であった。
Claims (13)
- 少なくとも1種のポリエステルマトリックス樹脂と、第2のバリア性樹脂とを含んでなるポリエステル樹脂組成物を製造する方法であって、
少なくとも一種のジカルボン酸と少なくとも1種のジオールとを、固相重合を行わずに重合させて、固有粘度が、フェノール60%および1,1,2,2−テトラクロロエタン40%の混合溶剤中(ここで、%は、フェノールおよび1,1,2,2−テトラクロロエタンの総重量に対する重量%である。)、30℃において、0.7〜0.9であるポリエステルマトリックス樹脂を得る工程、
上記工程において得られた溶融状態にある前記ポリエステルマトリックス樹脂に、第2のバリア性樹脂を混合してポリエステル樹脂組成物を形成する工程、および
前記ポリエステル樹脂組成物を冷却して固化させる工程、
を含んでなり、
前記ジカルボン酸が、ジカルボン酸モノマー単位の総モル数に対して、5〜30モル%の量のイソフタル酸単位を含み、
前記第2のバリア性樹脂が、メタ−キシレンジアミンと、アジピン酸および/またはイソフタル酸とを重合して得られたポリアミド樹脂である、ことを特徴とする、方法。 - 前記ポリエステルマトリックス樹脂の固有粘度が0.75〜0.85である、請求項1に記載の方法。
- 前記ポリエステルマトリックス樹脂の固有粘度が0.80〜0.85である、請求項1に記載の方法。
- 前記ポリエステルマトリックス樹脂が、イソフタル酸の重合した単位を、前記ポリエステル樹脂中にある全ての前記ジカルボン酸モノマー単位の総モル数に対して、10〜25モル%の量で含んでなる、請求項1に記載の方法。
- 前記ポリエステルマトリックス樹脂が、テレフタル酸およびエチレングリコールの反応した基を含んでなる、請求項1に記載の方法。
- 前記第2のバリア性樹脂が、受動的バリア性樹脂および/または能動的バリア性樹脂である、請求項1に記載の方法。
- 前記第2のバリア性樹脂が、前記ジカルボン酸含有重合体の総重量に対して6重量%までの量で含まれる、請求項1に記載の方法。
- 得られた溶融状態にある前記ポリエステルマトリックス樹脂に、第2のバリア性樹脂および充填材を混合してポリエステル樹脂組成物を形成する工程を、さらに含んでなる、請求項1に記載の方法。
- 得られた溶融状態にある前記ポリエステルマトリックス樹脂に、第2のバリア性樹脂/充填材のマスターバッチを混合してポリエステル樹脂組成物を形成する工程を含んでなる、請求項1に記載の方法。
- 前記充填材が、メタ−キシレンジアミンの重合した単位を含んでなるポリアミド中で剥離された有機クレーからなる群より選択される少なくとも1種である、請求項8または9に記載の方法。
- 前記充填材の縦横比が100〜400である、請求項10に記載に方法。
- 前記ポリエステルマトリックス樹脂が、ナフタレンジカルボン酸を、前記ポリエステル樹脂中にある全ての前記ジカルボン酸モノマー単位の総モル数に対して、2〜10モル%の量で含んでなる、請求項1に記載の方法。
- 前記ポリエステルマトリックス樹脂が、1,3−プロパンジオールを、前記ポリエステル樹脂中にあるジオールの総モル数に対して、2〜10モル%の量で含んでなる、請求項1に記載の方法。
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EP (2) | EP3153310B1 (ja) |
JP (2) | JP5933158B2 (ja) |
KR (1) | KR101334788B1 (ja) |
CN (1) | CN101309794A (ja) |
AU (1) | AU2006322074A1 (ja) |
CA (1) | CA2624799C (ja) |
WO (1) | WO2007067518A2 (ja) |
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JP5947209B2 (ja) * | 2009-06-09 | 2016-07-06 | エスケーシー カンパニー,リミテッド | 黒色シート及びその製造方法 |
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US20110256331A1 (en) | 2010-04-14 | 2011-10-20 | Dak Americas Llc | Ultra-high iv polyester for extrusion blow molding and method for its production |
US10899698B2 (en) | 2010-10-26 | 2021-01-26 | Ethox Chemicals, Llc | Bis(aryloxyalkyl) esters of aromatic polycarboxylic acids and method of preparation |
US8377530B2 (en) | 2011-02-08 | 2013-02-19 | Eastman Chemical Company | Polyesters with low molecular weight additives for improved gas barrier properties |
CA2870388C (en) * | 2011-09-12 | 2016-07-12 | Plastipak Packaging, Inc. | Monolayer carbon dioxide barrier pet bottles |
CN102586907B (zh) * | 2012-03-04 | 2014-01-22 | 江苏德赛化纤有限公司 | 阻燃中空涤纶纤维生产方法 |
JP6201502B2 (ja) * | 2013-08-09 | 2017-09-27 | 東洋製罐株式会社 | 透明性に優れた樹脂組成物及びその製造方法 |
AR100067A1 (es) | 2014-04-11 | 2016-09-07 | Dak Americas Llc | Método para mejorar la resistencia al impacto de un artículo moldeado por soplado con extrusión |
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2005
- 2005-12-06 US US11/294,370 patent/US20070128389A1/en not_active Abandoned
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2006
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- 2006-12-06 CA CA2624799A patent/CA2624799C/en active Active
- 2006-12-06 EP EP06844825A patent/EP1957260A4/en not_active Withdrawn
- 2006-12-06 AU AU2006322074A patent/AU2006322074A1/en not_active Abandoned
- 2006-12-06 KR KR1020087012170A patent/KR101334788B1/ko active IP Right Grant
- 2006-12-06 JP JP2008544429A patent/JP5933158B2/ja active Active
- 2006-12-06 WO PCT/US2006/046357 patent/WO2007067518A2/en active Application Filing
- 2006-12-06 CN CNA2006800426756A patent/CN101309794A/zh active Pending
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JP2009518517A (ja) | 2009-05-07 |
EP3153310B1 (en) | 2024-01-03 |
KR20080077610A (ko) | 2008-08-25 |
US20070128389A1 (en) | 2007-06-07 |
EP1957260A2 (en) | 2008-08-20 |
CN101309794A (zh) | 2008-11-19 |
JP2014240487A (ja) | 2014-12-25 |
CA2624799A1 (en) | 2007-06-14 |
WO2007067518A2 (en) | 2007-06-14 |
CA2624799C (en) | 2014-10-21 |
EP3153310A1 (en) | 2017-04-12 |
EP1957260A4 (en) | 2011-08-31 |
AU2006322074A1 (en) | 2007-06-14 |
WO2007067518A3 (en) | 2007-12-13 |
KR101334788B1 (ko) | 2013-12-02 |
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