JPWO2019004260A1 - エチレン−ビニルアルコール系共重合体組成物、ペレットおよび多層構造体 - Google Patents
エチレン−ビニルアルコール系共重合体組成物、ペレットおよび多層構造体 Download PDFInfo
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- JPWO2019004260A1 JPWO2019004260A1 JP2018534189A JP2018534189A JPWO2019004260A1 JP WO2019004260 A1 JPWO2019004260 A1 JP WO2019004260A1 JP 2018534189 A JP2018534189 A JP 2018534189A JP 2018534189 A JP2018534189 A JP 2018534189A JP WO2019004260 A1 JPWO2019004260 A1 JP WO2019004260A1
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- Prior art keywords
- evoh resin
- compound
- resin composition
- ethylene
- acid
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- 150000002506 iron compounds Chemical class 0.000 claims abstract description 50
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- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims abstract description 9
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- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Chemical compound CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 4
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- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 235000021355 Stearic acid Nutrition 0.000 description 3
- 150000001299 aldehydes Chemical class 0.000 description 3
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- 229910000399 iron(III) phosphate Inorganic materials 0.000 description 3
- 238000010030 laminating Methods 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 3
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- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- RCJMVGJKROQDCB-UHFFFAOYSA-N 2-methylpenta-1,3-diene Chemical compound CC=CC(C)=C RCJMVGJKROQDCB-UHFFFAOYSA-N 0.000 description 2
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Landscapes
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Abstract
Description
これにより、当該樹脂組成物は、フィッシュアイ等の欠点の発生および着色をより抑制し、成形品の外観性を向上させることができると共に、ロングラン性にもより優れると記載されている。
本発明のEVOH樹脂組成物は、EVOH樹脂(A)を主成分とし、共役ポリエン構造を有する化合物(B)および鉄化合物(C)を含有するものである。本発明のEVOH樹脂組成物は、ベース樹脂がEVOH樹脂(A)である。すなわち、EVOH樹脂組成物におけるEVOH樹脂(A)の含有量は、通常70重量%以上であり、好ましくは80重量%以上であり、より好ましくは90重量%以上であり、特に好ましくは95重量%以上である。以下、各成分について順に説明する。
本発明で用いるEVOH樹脂(A)は、通常、エチレンとビニルエステル系モノマーとの共重合体であるエチレン−ビニルエステル系共重合体をケン化させることにより得られる樹脂であり、非水溶性の熱可塑性樹脂である。上記ビニルエステル系モノマーとしては、経済的な面から、一般的には酢酸ビニルが用いられる。
本発明で用いられる共役ポリエン構造を有する化合物(B)とは、炭素−炭素二重結合と炭素−炭素単結合が交互に繋がってなる構造であって、炭素−炭素二重結合の数が2個以上である、いわゆる共役二重結合を有する化合物である。共役ポリエン構造を有する化合物(B)は、2個の炭素−炭素二重結合と1個の炭素−炭素単結合が交互に繋がってなる構造である共役ジエン化合物、3個の炭素−炭素二重結合と2個の炭素−炭素単結合が交互に繋がってなる構造である共役トリエン化合物、あるいはそれ以上の数の炭素−炭素二重結合と炭素−炭素単結合が交互に繋がってなる構造である共役ポリエン化合物であってもよい。ただし、上記共役ポリエン構造を有する化合物(B)としては、桂皮酸類等の芳香族カルボン酸類、およびハイドロキノン、ベンゾキノン等のキノン類を除く。
(1)EVOH樹脂組成物を凍結粉砕した粉末1gに対して、抽出溶媒(蒸留水:メタノール=1:1、体積比)8mLを添加する。
(2)この溶液に対し温度20℃、静置状態で超音波処理を1時間行い、樹脂中のソルビン酸を抽出し、冷却後に抽出溶媒で10mLに定容する。また、必要に応じて任意の倍率に希釈を行ってもよい。
(3)上記溶液をポアサイズ0.45μmのフィルターで濾過後、液体クロマトグラフ−紫外分光検出器で抽出溶液中のソルビン酸を測定する。
(4)上記の抽出溶媒を用いて調製したソルビン酸の標準溶液から検量線を作成し、絶対検量線法によって、ソルビン酸の含有量を定量する。
LCシステム :Agilent1260/1290[Agilent Technologies社製]
検出器 :Agilent1260 infinity ダイオードアレイ検出器[Agilent Technologies社製]
カラム :Cadenza CD−C18(100×3.0mm、3μm)[Imtakt社製]
カラム温度 :40℃
移動相A :0.05%ギ酸含有 5%アセトニトリルの水溶液
移動相B :0.05%ギ酸含有 95%アセトニトリルの水溶液
タイムプログラム:0.0→5.0分 B%=30%
5.0→8.0分 B%=30%→50%
8.0→10.0分 B%=50%
10.0→13.0分 B%=50%→30%
13.0→15.0分 B%=30%
流量 :0.2mL/分
UV検出波長 :190〜400nm
定量波長 :262nm
なお、上記HPLC測定条件における「%」は、体積%を意味する。
本発明のEVOH樹脂組成物は、上記EVOH樹脂(A)、上記共役ポリエン構造を有する化合物(B)に加え鉄化合物(C)を含有し、かつ、この鉄化合物(C)の含有量が特定微量であることを特徴とする。本発明のEVOH樹脂組成物は、上記のような構成を有するため、着色を抑制することができ、熱安定性に優れる。
本発明のEVOH樹脂組成物には、EVOH樹脂(A)以外の熱可塑性樹脂を、本発明の効果を阻害しない範囲(例えば、EVOH樹脂組成物の通常30重量%以下、好ましくは20重量%以下、特に好ましくは10重量%以下)にて含有することができる。
また、本発明のEVOH樹脂組成物には、本発明の効果を阻害しない範囲において、一般にEVOH樹脂に配合する配合剤が含有されていてもよい。例えば、無機複塩(例えば、ハイドロタルサイト等)、可塑剤(例えば、エチレングリコール、グリセリン、ヘキサンジオール等の脂肪族多価アルコール等)、酸素吸収剤[例えば、アルミニウム粉、亜硫酸カリウム、光触媒酸化チタン等の無機系酸素吸収剤;アスコルビン酸、さらにその脂肪酸エステルや金属塩等、ハイドロキノン、没食子酸、水酸基含有フェノールアルデヒド樹脂等の多価フェノール類、ビス−サリチルアルデヒド−イミンコバルト、テトラエチレンペンタミンコバルト、コバルト−シッフ塩基錯体、ポルフィリン類、大環状ポリアミン錯体、ポリエチレンイミン−コバルト錯体等の含窒素化合物と鉄以外の遷移金属との配位結合体、アミノ酸類とヒドロキシル基含有還元性物質との反応物、トリフェニルメチル化合物等の有機化合物系酸素吸収剤;窒素含有樹脂と鉄以外の遷移金属との配位結合体(例えば、メチルキシリレンジアミン(MXD)ナイロンとコバルトとの組合せ)、三級水素含有樹脂と鉄以外の遷移金属とのブレンド物(例えば、ポリプロピレンとコバルトとの組合せ)、炭素−炭素不飽和結合含有樹脂と鉄以外の遷移金属とのブレンド物(例えば、ポリブタジエンとコバルトの組合せ)、光酸化崩壊性樹脂(例えば、ポリケトン)、アントラキノン重合体(例えば、ポリビニルアントラキノン)等や、さらにこれらの配合物に光開始剤(ベンゾフェノン等)や過酸化物捕捉剤(市販の酸化防止剤等)や消臭剤(活性炭等)を添加したもの等の高分子系酸素吸収剤]、熱安定剤、光安定剤、紫外線吸収剤、着色剤、帯電防止剤、界面活性剤(ただし、滑剤として用いるものを除く)、抗菌剤、アンチブロッキング剤、充填材(例えば、無機フィラー等)等を配合してもよい。これらの化合物は、単独でもしくは2種以上併せて用いることができる。
上記の各成分を用いて、本発明のEVOH樹脂組成物を製造する方法としては、例えば、ドライブレンド法、溶融混合法、溶液混合法、含浸法等の公知の方法があげられ、これらを任意に組み合わせることも可能である。
EVOH樹脂組成物ぺレットの乾燥前重量(W1)を電子天秤にて秤量し、150℃の熱風乾燥機中で5時間乾燥させ、デシケーター中で30分間放冷後の重量(W2)を秤量し、下記式より算出する。
含水率(重量%)=[(W1−W2)/W1]×100
重量減少割合(%)=[(加熱前重量−加熱後重量)/加熱前重量]×100
本発明の多層構造体は、上記本発明のEVOH樹脂組成物からなる層を備えるものである。本発明のEVOH樹脂組成物からなる層(以下、「EVOH樹脂組成物層」と称する。)は、本発明のEVOH樹脂組成物以外の熱可塑性樹脂を主成分とする他の基材(以下、「基材樹脂」と称する。)と積層することで、さらに強度を付与したり、EVOH樹脂組成物層を水分等の影響から保護したり、他の機能を付与することができる。
なお、例中「部」とあるのは、断りのない限り重量基準を意味する。
・EVOH樹脂(A):エチレン構造単位の含有量29モル%、ケン化度99.6モル%、MFR3.9g/10分(210℃、荷重2160g)のエチレン−ビニルアルコール共重合体
上記EVOH樹脂(A)のペレットを粉砕したサンプル0.5gを赤外線加熱炉で灰化処理(酸素気流中650℃、1時間)し、灰分を酸溶解して純水で定容したものを試料溶液とした。この溶液を下記のICP−MS(Agilent Technologies社製 ICP質量分析装置 7500ce型)を用いて標準添加法で測定した。その結果、鉄化合物(C)の含有量は、金属換算にて0ppmであった。
上記EVOH樹脂(A)のペレット100部、共役ポリエン構造を有する化合物(B)としてソルビン酸(分子量112)0.01部(EVOH樹脂組成物の重量あたり100ppm)、鉄化合物(C)としてリン酸鉄(III)n水和物(和光純薬工業社製、230℃乾燥減量 20.9重量%)0.000034部(EVOH樹脂組成物の重量あたり金属換算にて0.1ppm)をプラストグラフ(ブラベンダー社製)にて、230℃において5分間予熱したのち5分間溶融混練し、実施例1のEVOH樹脂組成物を得た。得られたEVOH樹脂組成物を、粉砕機(ソメタニ産業社製 型式:SKR16−240)で650rpmにて粉砕して粉砕物を得た。かかる粉砕物は、1〜5mm角の小片であった。
実施例1において、リン酸鉄(III)n水和物の配合量を0.00034部(EVOH樹脂組成物の重量あたり金属換算にて1ppm)に変更した以外は、実施例1と同様にして実施例2のEVOH樹脂組成物を得た。
実施例1において、リン酸鉄(III)n水和物の配合量を0.0034部(EVOH樹脂組成物の重量あたり金属換算にて10ppm)に変更した以外は、実施例1と同様にして実施例3のEVOH樹脂組成物を得た。
実施例1において、リン酸鉄(III)n水和物を配合しなかった以外は同様にして比較例1のEVOH樹脂組成物を得た。
日本電色工業社製 分光色差計 SE6000を用いて、EVOH樹脂組成物の粉砕品を空気雰囲気下のオーブン内で150℃、5時間加熱したEVOH樹脂組成物におけるYI値を測定した。このとき、内径32mm高さ30mmの円筒に上記加熱したEVOH樹脂組成物を充填し、擦りきった状態で測定に供した。かかる値が大きいほど、EVOH樹脂組成物が黄色く着色していることを意味する。
上記で得られたEVOH樹脂組成物の粉砕物を5mg用い、熱重量測定装置(Perkin Elmer社製、Pyris 1 TGA)により、窒素雰囲気下、気流速度:20mL/分、温度:230℃、時間:1時間の条件下での加熱前後の重量から下記式より、重量減少割合を算出した。
重量減少割合(%)=[(加熱前重量−加熱後重量)/加熱前重量]×100
得られた重量減少割合の小数点第2位を四捨五入し、下記の評価基準に基づいて、熱安定性を評価した。
A:0.9% 熱安定性に特に優れる
B:0.8%、または、1.0% 熱安定性に非常に優れる
C:0.7%、または、1.1% 熱安定性に優れる
D:0.6% 熱安定性に劣る
E:〜0.5%、または、1.2%以上〜 熱安定性に非常に劣る
Claims (5)
- エチレン−ビニルアルコール系共重合体(A)、共役ポリエン構造を有する化合物(B)および鉄化合物(C)を含有するエチレン−ビニルアルコール系共重合体組成物であって、上記鉄化合物(C)の含有量がエチレン−ビニルアルコール系共重合体組成物の重量あたり金属換算にて0.01〜20ppmであることを特徴とするエチレン−ビニルアルコール系共重合体組成物。
- 上記共役ポリエン構造を有する化合物(B)の含有量がエチレン−ビニルアルコール系共重合体組成物の重量あたり1〜30000ppmであることを特徴とする請求項1記載のエチレン−ビニルアルコール系共重合体組成物。
- 金属換算での上記鉄化合物(C)の含有量に対する、上記共役ポリエン構造を有する化合物(B)の含有量の重量比率が、共役ポリエン構造を有する化合物(B)の含有量/金属換算での鉄化合物(C)の含有量=0.2〜50000であることを特徴とする請求項1または2に記載のエチレン−ビニルアルコール系共重合体組成物。
- 請求項1〜3のいずれか一項に記載のエチレン−ビニルアルコール系共重合体組成物からなることを特徴とするペレット。
- 請求項1〜3のいずれか一項に記載のエチレン−ビニルアルコール系共重合体組成物からなる層を備えることを特徴とする多層構造体。
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