JP7156035B2 - 樹脂組成物、溶融成形用材料、多層構造体および液体包装用材料 - Google Patents
樹脂組成物、溶融成形用材料、多層構造体および液体包装用材料 Download PDFInfo
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- JP7156035B2 JP7156035B2 JP2018562131A JP2018562131A JP7156035B2 JP 7156035 B2 JP7156035 B2 JP 7156035B2 JP 2018562131 A JP2018562131 A JP 2018562131A JP 2018562131 A JP2018562131 A JP 2018562131A JP 7156035 B2 JP7156035 B2 JP 7156035B2
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- olefin
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- polymer
- evoh
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Description
また、本発明において、「(メタ)アクリル」とはアクリルあるいはメタクリルを意味するものである。
本発明の樹脂組成物は、EVOH(A)、オレフィン系ポリマー(B)およびソルビン酸エステル(C)を含有する。以下、本発明の樹脂組成物の各成分について順に説明する。
本発明で用いるEVOH(A)は、通常、エチレンとビニルエステル系モノマーとを共重合させた後にケン化させることにより得られる樹脂であり、一般的にエチレン-ビニルアルコール系共重合体やエチレン-ビニルエステル系共重合体ケン化物と称される非水溶性の熱可塑性樹脂である。重合法も公知の任意の重合法、例えば、溶液重合、懸濁重合、エマルジョン重合を用いることができるが、一般的にはメタノールを溶媒とする溶液重合が用いられる。得られたエチレン-ビニルエステル系共重合体のケン化も公知の方法で行い得る。
すなわち、本発明で用いるEVOH(A)は、エチレン構造単位とビニルアルコール構造単位を主とし、通常、ケン化されずに残存した若干量のビニルエステル構造単位を含むものである。
上記コモノマーとしては、例えば、2-プロペン-1-オール、3-ブテン-1-オール、4-ペンテン-1-オール、5-ヘキセン-1-オール、3,4-ジヒドロキシ-1-ブテン、5-ヘキセン-1,2-ジオール等の水酸基含有α-オレフィン類や、そのエステル化物である、3,4-ジアシロキシ-1-ブテン、3,4-ジアセトキシ-1-ブテン、2,3-ジアセトキシ-1-アリルオキシプロパン、2-アセトキシ-1-アリルオキシ-3-ヒドロキシプロパン、3-アセトキシ-1-アリルオキシ-2-ヒドロキシプロパン、グリセリンモノビニルエーテル、グリセリンモノイソプロペニルエーテル等、水酸基含有α-オレフィン類のアシル化物等の誘導体、1,3-ヒドロキシ-2-メチレンプロパン、1,5-ヒドロキシ-3-メチレンペンタン等のヒドロキシメチルビニリデン類;これらのエステル化物である1,3-ジアセトキシ-2-メチレンプロパン、1,3-ジプロピオニルオキシ-2-メチレンプロパン、1,3-ジブチロニルオキシ-2-メチレンプロパン等のビニリデンジアセテート類;アクリル酸、メタクリル酸、クロトン酸、(無水)フタル酸、(無水)マレイン酸、(無水)イタコン酸等の不飽和酸類あるいはその塩あるいは炭素数1~18のモノまたはジアルキルエステル類、アクリルアミド、炭素数1~18のN-アルキルアクリルアミド、N,N-ジメチルアクリルアミド、2-アクリルアミドプロパンスルホン酸あるいはその塩、アクリルアミドプロピルジメチルアミンあるいはその酸塩あるいはその4級塩等のアクリルアミド類、メタアクリルアミド、炭素数1~18のN-アルキルメタクリルアミド、N,N-ジメチルメタクリルアミド、2-メタクリルアミドプロパンスルホン酸あるいはその塩、メタクリルアミドプロピルジメチルアミンあるいはその酸塩あるいはその4級塩等のメタクリルアミド類、N-ビニルピロリドン、N-ビニルホルムアミド、N-ビニルアセトアミド等のN-ビニルアミド類、アクリルニトリル、メタクリルニトリル等のシアン化ビニル類、炭素数1~18のアルキルビニルエーテル、ヒドロキシアルキルビニルエーテル、アルコキシアルキルビニルエーテル等のビニルエーテル類、塩化ビニル、塩化ビニリデン、フッ化ビニル、フッ化ビニリデン、臭化ビニル等のハロゲン化ビニル化合物類、トリメトキシビニルシラン等のビニルシラン類、酢酸アリル、塩化アリル等のハロゲン化アリル化合物類、アリルアルコール、ジメトキシアリルアルコール等のアリルアルコール類、トリメチル-(3-アクリルアミド-3-ジメチルプロピル)-アンモニウムクロリド、アクリルアミド-2-メチルプロパンスルホン酸等のコモノマーがあげられる。これらは単独でもしくは2種以上併せて用いることができる。
本発明で用いられる、オレフィン系ポリマー(B)は、炭素-炭素二重結合を含有する脂肪族炭化水素モノマーであるオレフィンを主モノマーとし、通常、数平均分子量1万以上の高分子で、主鎖が炭素結合のみで構成される親油性ポリマーをいう。具体的には、ポリオレフィン、オレフィン系熱可塑性エラストマー、脂肪族系ゴム、オレフィン-(メタ)アクリル酸エステル共重合体、アイオノマーがあげられる。これらのオレフィン系ポリマー(B)は、単独でもしくは2種以上を併せて用いることができる。なかでも、ポリオレフィンが好ましい。
上記ポリオレフィンとは、例えば、エチレン、プロピレン、ブテン等のオレフィンモノマーのホモポリマー、2種以上のオレフィンモノマーのランダムコポリマー、ブロックコポリマーをいう。なかでも、オレフィンホモポリマーとしては、例えば、超低密度ポリエチレン、(直鎖状)低密度ポリエチレン、高密度ポリエチレン等のポリエチレン、ポリプロピレン、ポリブテン、ポリメチルペンテン等があげられる。オレフィンブロックコポリマーとしては、エチレン-プロピレン共重合体、エチレン-ブテン共重合体、エチレン-ヘキセン共重合体、エチレン-オクテン共重合体等のエチレン-α-オレフィン共重合体;プロピレン-エチレン共重合体、プロピレン-ブテン共重合体等のプロピレン-α-オレフィン共重合体;ブテン-エチレン共重合体、ブテン-プロピレン共重合体等のブテン-α-オレフィン共重合体等があげられる。オレフィンランダムコポリマーとしては、上記オレフィンモノマーを2種以上ランダムに共重合したもので、低結晶性を示し、例えば、三井化学社製のエチレン系タフマー、プロピレン系タフマー、ブテン系タフマー等のタフマーシリーズ(商品名)等があげられる。
市販品としては、例えば、エチレン系ポリマー(三井化学社製のタフマーDF&H)、プロピレン系ポリマー(三井化学社製のタフマーH、タフマーXM)、ブテン系ポリマー(三井化学社製のタフマーBL)等があげられる。
上記カルボン酸変性オレフィン系ポリマー(B2)は、上記オレフィン系ポリマー、すなわち、ポリオレフィン、オレフィン系熱可塑性エラストマー、脂肪族系ゴム、オレフィン-(メタ)アクリル酸エステル共重合体、アイオノマー等の通常、数平均分子量1万以上の高分子で、主鎖が炭素結合のみで構成される親油性ポリマーが、カルボン酸によって変性されているものである。
EVOH(A)の溶融粘度とカルボン酸変性オレフィン系ポリマー(B2)との溶融粘度が近いほど、溶融混練が容易になり、耐屈曲性、透明性に優れた樹脂組成物が得られやすい。具体的には、210℃、荷重2160g条件下で測定したMFR値の比(EVOH(A)/カルボン酸変性オレフィン系ポリマー(B2))が、通常0.1~10、好ましくは0.5~7.5である。
また、本発明で用いられるカルボン酸変性オレフィン系ポリマー(B2)成分としては、本発明の効果を阻害しない範囲において、カルボン酸変性オレフィン系ポリマー(B2)成分に含有されるカルボン酸成分を部分的に他の化合物(例えば、ポリアミド6、ポリアミド6/12等のポリアミド樹脂)によって後変性した変性重合体であってもよい。
本発明は、EVOH(A)およびオレフィン系ポリマー(B)を含有する樹脂組成物において、ソルビン酸エステル(C)を特定微量にて配合することにより、着色を抑制するという顕著な効果を奏するものである。
このようにして、常にラジカルを捕捉可能なソルビン酸が生成することから、樹脂組成物において、ラジカルの発生した早い段階でラジカルを捕捉することが可能となり、優れた着色抑制効果が得られると推測される。本発明においては、ソルビン酸エステル(C)の配合量が特定微量である場合、上記のサイクルが効率よく働き、顕著な着色抑制効果が得られるものと推測される。
本発明の樹脂組成物においては、分散助剤として炭化水素系樹脂(D)をさらに配合することが好ましい。本発明において、上記炭化水素系樹脂(D)は、数平均分子量が通常100から3000で、かつ軟化点が通常60℃以上170℃未満の樹脂である。このような炭化水素系樹脂(D)は、通常、常温で液体または固体の熱可塑性樹脂に属する。
なかでも上記の芳香族系石油樹脂、または脂肪族/芳香族系石油樹脂を水素添加して得られた水添系石油樹脂が代表的であり、具体例としては、アルコン(荒川化学工業社製)、アイマーブ(出光興産社製)、エスコレッツ5000シリーズ(エクソンモービル社製)等があげられる。
かかる水添系石油樹脂の場合には、水添率によって樹脂の極性が異なり、主に水添率90%以上の完全水添型と水添率90%未満の部分水添型の2種類に分類される。前者の具体例としては、アルコンPグレード(荒川化学工業社製)、アイマーブPタイプ(出光興産社製)等があげられ、後者の具体例としては、アルコンMグレード(荒川化学工業社製)、アイマーブSタイプ(出光興産社製)等があげられる。
また、水添系石油樹脂の水添率については、特に限定されないが、未変性オレフィン系ポリマー(B1)を用いた場合の親和性を考慮すると、完全水添型の水添系石油樹脂を用いることが好ましい。
本発明の樹脂組成物には、EVOH(A)、オレフィン系ポリマー(B)および炭化水素系樹脂(D)以外に、さらに樹脂成分として、他の熱可塑性樹脂を、樹脂組成物に対して、通常10重量%以下、好ましくは5重量%以下、特に好ましくは3重量%以下となるような範囲内で含有してもよい。
本発明の樹脂組成物には、上記各成分の他、必要に応じて、本発明の効果を損なわない範囲内(例えば、通常樹脂組成物全体の10重量%以下、好ましくは5重量%以下、特に好ましくは3重量%以下の含有割合)において、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の可塑剤;高級脂肪酸(例えばラウリン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸、オレイン酸等)、高級脂肪酸の金属塩(例えばステアリン酸カルシウム、ステアリン酸マグネシウム等)、高級脂肪酸エステル(高級脂肪酸のメチルエステル、イソプロピルエステル、ブチルエステル、オクチルエステル等)、高級脂肪族アミド(例えばステアリン酸アミド等、オレイン酸アミド等)、ビス高級脂肪酸アミド(例えばエチレンビスステアリン酸アミド等)、低分子量ポリオレフィン(例えば、数平均分子量10000未満の低分子量ポリエチレン、または低分子量ポリプロピレン)等の滑剤;乾燥剤;酸素吸収剤;熱安定剤;光安定剤;難燃剤;架橋剤;硬化剤;発泡剤;結晶核剤;防曇剤;生分解用添加剤;シランカップリング剤;アンチブロッキング剤;酸化防止剤;着色剤;帯電防止剤;紫外線吸収剤;抗菌剤;不溶性無機複塩(例えば、ハイドロタルサイト等);界面活性剤;ワックス等の公知の添加剤を適宜配合することができる。これらは単独でもしくは2種以上併せて用いることができる。
これらのうち、特に、酢酸、ホウ酸およびその塩を含むホウ素化合物、酢酸塩、リン酸塩を配合することが好ましい。
本発明の樹脂組成物は、前記必須成分であるEVOH(A)、オレフィン系ポリマー(B)およびソルビン酸エステル(C)と、必要に応じて、炭化水素系樹脂(D)および、上記の各任意成分を用いて製造されるが、製造方法としては、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。
室温(25℃)下において、樹脂組成物の乾燥前重量(W1)を電子天秤にて秤量する。その後、この試料を150℃の熱風乾燥機中で5時間乾燥させる。乾燥後、デシケーター中で30分間放冷して樹脂組成物の温度を室温(25℃)に戻した後の重量(W2)を秤量し、下記式より算出する。
含水率(重量%)=[(W1-W2)/W1]×100
本発明の多層構造体は、上記本発明の樹脂組成物からなる層を備えるものである。本発明の樹脂組成物からなる層(以下、「樹脂組成物層」と称する。)は、本発明の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、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(A):エチレン構造単位の含有量29モル%、ケン化度100モル%、MFR3.2g/10分(210℃、荷重2160g)のエチレン-ビニルアルコール共重合体
・未変性オレフィン系ポリマー(B1-1):エチレン-ブテンランダム共重合体(三井化学社製「タフマーA-4085S」;密度0.89g/cm3、23℃、50%RHにおける曲げ弾性率30MPa、MFR(210℃、2160g荷重)5.2g/10分
・カルボン酸変性オレフィン系ポリマー(B2-1):無水マレイン酸変性ポリプロピレン(LyondellBasell社製)「Plexar PX6002」;密度0.89g/cm3、MFR(210℃、2160g荷重)2.3g/10分
上記EVOH(A)のペレット80部、上記未変性オレフィン系ポリマー(B1-1)のペレット20部をドライブレンドした。その後ドライブレンドしたペレット100部、ソルビン酸エステル(C)としてソルビン酸メチル(富士フイルム和光純薬社製、分子量126)0.0000004部(樹脂組成物の重量当たり0.004ppm)をプラストグラフ(ブラベンダー社製)にて、230℃で5分間予熱したのち、230℃、50rpmにおいて5分間溶融混練し、その後冷却固化させ、塊状の樹脂組成物を得た。
得られた樹脂組成物を、粉砕機(ソメタニ産業社製、型式:SKR16-240)を用い、回転刃の回転数650rpmにて粉砕して粉砕物を得た。かかる粉砕物は、1mm角から5mm角の小片であった。かかる樹脂組成物の含水率は、0.15%であった。
実施例1において、ソルビン酸メチルの配合量を0.00008部(樹脂組成物の重量当たり0.8ppm)に変更した以外は、実施例1と同様にして実施例2の樹脂組成物およびその粉砕物を得た。かかる樹脂組成物の含水率は、0.18%であった。
実施例1において、ソルビン酸メチルをソルビン酸エチル(富士フイルム和光純薬社製、分子量140)に変更した以外は、実施例1と同様にして実施例3の樹脂組成物およびその粉砕物を得た。かかる樹脂組成物の含水率は、0.17%であった。
実施例1において、未変性オレフィン系ポリマー(B1-1)をカルボン酸変性オレフィン系ポリマー(B2-1)に変更した以外は、実施例1と同様にして実施例4の樹脂組成物およびその粉砕物を得た。かかる樹脂組成物の含水率は、0.16%であった。
実施例1において、ソルビン酸メチルを配合しなかった以外は実施例1と同様にして比較例1の樹脂組成物およびその粉砕物を得た。かかる樹脂組成物の含水率は、0.18%であった。
実施例1において、ソルビン酸メチルの配合量を0.0012部(樹脂組成物の重量当たり12ppm)に変更した以外は、実施例1と同様にして比較例2の樹脂組成物およびその粉砕物を得た。かかる樹脂組成物の含水率は、0.14%であった。
樹脂組成物を5mg用い、熱重量測定装置(Pyris 1 TGA,Perkin Elmer社製)により、窒素雰囲気下、気流速度:20mL/分、温度:230℃、時間:1時間の条件下での重量減少率を測定した。かかる値が低い場合、樹脂組成物が分解していないことを意味しており、樹脂組成物の熱安定性に優れることを意味する。
上記の各粉砕物をサンプルとし、ビジュアルアナライザー IRIS VA400(Alpha mos社製)にて、色番号「4076」(R:248、G:232、B:200)、「4077」(R:248、G:232、B:216)「4078」(R:248、G:232、B:232)の総和に対する色番号「4093」(R:248、G:248、B:216)、「4094」(R:248、G:248、B:232)、「4095」(R:248、G:248、B:248)が占める割合(「4076+4077+4078」/「4093+4094+4095」)、を評価した。色番号「4076」「4077」「4078」は、濃い黄色味を有する色であり、色番号「4093」「4094」「4095」は、薄い黄色味を有する色であり、濃い黄色味の割合が大きいほど、サンプルが黄色く着色していることを意味する。
一方で実施例1~4では、比較例2よりもソルビン酸エステル(C)の配合量が少ないにもかかわらず、熱安定性を損なわずに、比較例2よりも高い着色抑制効果が得られた。したがって、本発明の樹脂組成物が顕著な着色抑制効果が得られることがわかる。なお、本発明の着色評価は230℃で5分間予熱したのち、5分間溶融混練した樹脂組成物を評価している。ここで、工業的な溶融成形においては、押出機やダイス等の中で数時間~数日間にわたり滞留した結果、加熱を受け続ける樹脂組成物が存在することがあり、本発明の着色評価における差が増幅されることになる。そのため、本発明の着色評価における0.1の差は、工業的に有意な差といえる。
Claims (8)
- エチレン-ビニルアルコール系共重合体(A)、オレフィン系ポリマー(B)およびソルビン酸エステル(C)を含有する樹脂組成物であって、上記オレフィン系ポリマー(B)に対するエチレン-ビニルアルコール系共重合体(A)の重量含有比率が、エチレン-ビニルアルコール系共重合体(A)/オレフィン系ポリマー(B)=50/50~99/1であり、上記ソルビン酸エステル(C)の含有量が、樹脂組成物の重量当たり0.00001~10ppmであることを特徴とする樹脂組成物。
- 上記ソルビン酸エステル(C)が、アルコキシ基の炭素数が1~5のソルビン酸アルキルエステルであることを特徴とする請求項1記載の樹脂組成物。
- 上記オレフィン系ポリマー(B)が、ポリオレフィン、オレフィン系熱可塑性エラスト マー、脂肪族系ゴム、オレフィン-(メタ)アクリル酸エステル共重合体、およびアイオノマーからなる群から選ばれる少なくとも1種であることを特徴とする請求項1または2記載の樹脂組成物。
- 上記オレフィン系ポリマー(B)の密度が、0.85~0.96g/cm3であることを特徴とする請求項1~3のいずれか一項に記載の樹脂組成物。
- 上記オレフィン系ポリマー(B)の、23℃、50%RHにおける曲げ弾性率が150MPa未満であることを特徴とする請求項1~4のいずれか一項に記載の樹脂組成物。
- 請求項1~5のいずれか一項に記載の樹脂組成物からなることを特徴とする溶融成形用材料。
- 請求項1~5のいずれか一項に記載の樹脂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。
- 請求項7記載の多層構造体からなることを特徴とする液体包装用材料。
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WO2015041258A1 (ja) | 2013-09-20 | 2015-03-26 | 株式会社クラレ | 熱成形容器及びその製造方法 |
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JP2011202147A (ja) | 2010-03-02 | 2011-10-13 | Nippon Synthetic Chem Ind Co Ltd:The | 樹脂組成物並びにこれを用いた成形品及び多層構造体 |
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WO2015041258A1 (ja) | 2013-09-20 | 2015-03-26 | 株式会社クラレ | 熱成形容器及びその製造方法 |
WO2015050211A1 (ja) | 2013-10-03 | 2015-04-09 | 株式会社クラレ | 樹脂組成物、多層構造体及びそれからなる熱成形容器 |
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JPWO2019103080A1 (ja) | 2020-10-08 |
US20200263010A1 (en) | 2020-08-20 |
EP3715421A1 (en) | 2020-09-30 |
TWI795472B (zh) | 2023-03-11 |
WO2019103080A1 (ja) | 2019-05-31 |
CN111356739A (zh) | 2020-06-30 |
TW201930438A (zh) | 2019-08-01 |
CN111356739B (zh) | 2024-03-12 |
US11661502B2 (en) | 2023-05-30 |
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