JP7268356B2 - エチレン-ビニルアルコール系共重合体組成物、溶融成形用材料、多層構造体および熱成形容器用材料 - Google Patents
エチレン-ビニルアルコール系共重合体組成物、溶融成形用材料、多層構造体および熱成形容器用材料 Download PDFInfo
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- JP7268356B2 JP7268356B2 JP2018562125A JP2018562125A JP7268356B2 JP 7268356 B2 JP7268356 B2 JP 7268356B2 JP 2018562125 A JP2018562125 A JP 2018562125A JP 2018562125 A JP2018562125 A JP 2018562125A JP 7268356 B2 JP7268356 B2 JP 7268356B2
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- ethylene
- evoh
- vinyl alcohol
- resin composition
- alcohol copolymer
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- 229920000219 Ethylene vinyl alcohol Polymers 0.000 title claims description 301
- 239000000203 mixture Substances 0.000 title claims description 20
- 239000012778 molding material Substances 0.000 title claims description 6
- 239000012611 container material Substances 0.000 title claims description 4
- 238000003856 thermoforming Methods 0.000 title description 6
- 239000004715 ethylene vinyl alcohol Substances 0.000 claims description 265
- 238000000034 method Methods 0.000 claims description 79
- -1 sorbic acid ester Chemical class 0.000 claims description 79
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 75
- 239000005977 Ethylene Substances 0.000 claims description 75
- 229940075582 sorbic acid Drugs 0.000 claims description 48
- 239000004334 sorbic acid Substances 0.000 claims description 48
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- 238000002156 mixing Methods 0.000 claims description 40
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- 229940075554 sorbate Drugs 0.000 claims description 11
- WSWCOQWTEOXDQX-MQQKCMAXSA-M (E,E)-sorbate Chemical compound C\C=C\C=C\C([O-])=O WSWCOQWTEOXDQX-MQQKCMAXSA-M 0.000 claims description 8
- KWKVAGQCDSHWFK-VNKDHWASSA-N Methyl sorbate Chemical compound COC(=O)\C=C\C=C\C KWKVAGQCDSHWFK-VNKDHWASSA-N 0.000 claims description 8
- 239000001375 methyl (2E,4E)-hexa-2,4-dienoate Substances 0.000 claims description 8
- OZZYKXXGCOLLLO-TWTPFVCWSA-N ethyl (2e,4e)-hexa-2,4-dienoate Chemical compound CCOC(=O)\C=C\C=C\C OZZYKXXGCOLLLO-TWTPFVCWSA-N 0.000 claims description 4
- 229920000642 polymer Polymers 0.000 claims description 3
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims 3
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 description 291
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- 150000003839 salts Chemical class 0.000 description 11
- 239000004711 α-olefin Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
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- BEFDCLMNVWHSGT-UHFFFAOYSA-N ethenylcyclopentane Chemical compound C=CC1CCCC1 BEFDCLMNVWHSGT-UHFFFAOYSA-N 0.000 description 4
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- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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- 239000002253 acid Substances 0.000 description 3
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- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 2
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- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 2
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- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- 239000004594 Masterbatch (MB) Substances 0.000 description 2
- 229910019142 PO4 Inorganic materials 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 2
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- KGBXLFKZBHKPEV-UHFFFAOYSA-N boric acid Chemical compound OB(O)O KGBXLFKZBHKPEV-UHFFFAOYSA-N 0.000 description 2
- 239000004327 boric acid Substances 0.000 description 2
- 229910052796 boron Inorganic materials 0.000 description 2
- 159000000007 calcium salts Chemical class 0.000 description 2
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- 239000003795 chemical substances by application Substances 0.000 description 2
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- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
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- 238000004993 emission spectroscopy Methods 0.000 description 2
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- 239000004702 low-density polyethylene Substances 0.000 description 2
- 159000000003 magnesium salts Chemical class 0.000 description 2
- HQKMJHAJHXVSDF-UHFFFAOYSA-L magnesium stearate Chemical compound [Mg+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O HQKMJHAJHXVSDF-UHFFFAOYSA-L 0.000 description 2
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
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- 229920005604 random copolymer Polymers 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- WSWCOQWTEOXDQX-MQQKCMAXSA-N sorbic acid group Chemical class C(\C=C\C=C\C)(=O)O WSWCOQWTEOXDQX-MQQKCMAXSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- 150000003751 zinc Chemical class 0.000 description 2
- BQCIDUSAKPWEOX-UHFFFAOYSA-N 1,1-Difluoroethene Chemical compound FC(F)=C BQCIDUSAKPWEOX-UHFFFAOYSA-N 0.000 description 1
- BCITXCOYSHAADW-UHFFFAOYSA-N 1-[2-(4-oxoheptoxymethyl)prop-2-enoxy]heptan-4-one Chemical compound C(CCC(=O)CCC)OCC(COCCCC(=O)CCC)=C BCITXCOYSHAADW-UHFFFAOYSA-N 0.000 description 1
- JNBLCHLVUYMNLH-UHFFFAOYSA-N 1-acetyloxyethenyl acetate Chemical class CC(=O)OC(=C)OC(C)=O JNBLCHLVUYMNLH-UHFFFAOYSA-N 0.000 description 1
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- QLZJUIZVJLSNDD-UHFFFAOYSA-N 2-(2-methylidenebutanoyloxy)ethyl 2-methylidenebutanoate Chemical class CCC(=C)C(=O)OCCOC(=O)C(=C)CC QLZJUIZVJLSNDD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- OEPOKWHJYJXUGD-UHFFFAOYSA-N 2-(3-phenylmethoxyphenyl)-1,3-thiazole-4-carbaldehyde Chemical compound O=CC1=CSC(C=2C=C(OCC=3C=CC=CC=3)C=CC=2)=N1 OEPOKWHJYJXUGD-UHFFFAOYSA-N 0.000 description 1
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- LANDRZNMJOEVQO-UHFFFAOYSA-N 3-ethenoxypropane-1,2-diol Chemical compound OCC(O)COC=C LANDRZNMJOEVQO-UHFFFAOYSA-N 0.000 description 1
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- SCVZKPKDMFXESQ-VSAQMIDASA-N butyl (2e,4e)-hexa-2,4-dienoate Chemical compound CCCCOC(=O)\C=C\C=C\C SCVZKPKDMFXESQ-VSAQMIDASA-N 0.000 description 1
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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Description
そこで、本発明はこのような背景下において、融点の異なる2種以上のEVOHを含有するEVOH樹脂組成物において、着色抑制効果に優れたEVOH樹脂組成物を提供する。
本発明のEVOH樹脂組成物は、エチレン含有量が異なる2種以上のEVOHを有するEVOH(A)とソルビン酸エステル(B)とを含有する。また、本発明のEVOH樹脂組成物は、EVOH(A)を主成分とするものである。すなわち、EVOH樹脂組成物におけるEVOH(A)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%以上である。以下、本発明のEVOH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。そして、本発明で用いるEVOH(A)は、エチレン含有量が異なる2種以上のEVOHを有するものである。なお、本発明においてEVOHのエチレン含有量は、ISO14663に基づいて測定した値を意味する。
また、EVOH樹脂組成物に何種類のエチレン含有量が異なるEVOHが含まれているかは、上記のDSCを用いて測定されるピークの数から確認することができる。
本発明は、エチレン含有量が異なる2種以上のEVOH(A)を含有するEVOH樹脂組成物において、ソルビン酸エステル(B)を特定微量にて配合することにより、着色抑制効果に優れ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、EVOH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(B)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EVOH樹脂組成物には、EVOH(A)以外に、さらに樹脂成分として、他の熱可塑性樹脂を、本発明の効果を阻害しない範囲(例えばEVOH樹脂組成物に対して、通常30重量%以下、好ましくは10重量%以下)で含有してもよい。
本発明のEVOH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、EVOH樹脂組成物全体の10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、分子量500~10000程度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;無機フィラー;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EVOH樹脂組成物は、前記必須成分であるEVOH(A)およびソルビン酸エステル(B)と必要に応じて配合される上記の各任意成分を用いて製造される。かかる製造方法として具体的には、例えばエチレン含有量が異なる複数種のEVOHを混合して、EVOH(A)を製造し、かかるEVOH(A)にソルビン酸エステル(B)を配合する方法、EVOH(A)を構成する少なくとも1種のEVOHにソルビン酸エステル(B)を配合し、これに他のEVOH(A)を構成する少なくとも1種のEVOHを配合する方法、EVOH(A)を構成する少なくとも1種のEVOHにソルビン酸エステル(B)の一部を配合し、他のEVOH(A)を構成する少なくとも1種のEVOHにソルビン酸エステル(B)の一部を配合し、両者を混合する方法等が挙げられる。
室温(25℃)下において、EVOH樹脂組成物を試料とし、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EVOH樹脂組成物の温度を室温に戻した後の重量(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。
上記延伸処理は、一軸延伸、二軸延伸のいずれであってもよく、二軸延伸の場合は同時延伸であっても逐次延伸であってもよい。また、延伸方法としてはロール延伸法、テンター延伸法、チューブラー延伸法、延伸ブロー法、真空圧空成形等のうち延伸倍率の高いものも採用できる。延伸温度は、多層構造体の融点近傍の温度で、通常40~170℃、好ましくは60~160℃程度の範囲から選ばれる。延伸温度が低すぎる場合は延伸性が不良となる傾向があり、高すぎる場合は安定した延伸状態を維持することが困難となる傾向がある。
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(A1):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
・EVOH(A2):エチレン構造単位の含有量38モル%、ケン化度100モル%、MFR4.3g/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(A1)のペレット80部、上記EVOH(A2)のペレット20部をドライブレンドしEVOH(A)を得た。その後、上記EVOH(A)100部、ソルビン酸エステル(B)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)0.0000005部(EVOH樹脂組成物の重量当たり0.005ppm)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の条件下において5分間溶融混練し、その後冷却固化させ、塊状の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)を用い、回転刃の回転数650rpmにて粉砕して粉砕物を得た。また、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、0.17%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0.0001部(EVOH樹脂組成物の重量当たり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、0.20%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EVOH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。
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EVOH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、0.13%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0.0015部(EVOH樹脂組成物の重量当たり15ppm)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、0.20%であった。
上記で得られたEVOH樹脂組成物の粉砕物を、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)が占める割合を評価した。色番号「4076」は、黄色味を有する色であり、この割合が大きいほど、EVOH樹脂組成物が黄色く着色していることを意味する。
これに対して異なる2種のEVOHを含有し、さらに特定微量のソルビン酸エステル(B)を含有する実施例1~3のEVOH樹脂組成物は、ソルビン酸エステル(B)の配合量が比較例2より少ないにも関わらず、EVOH樹脂組成物の着色が著しく改善した。
したがって、本発明のEVOH樹脂組成物は、EVOH樹脂組成物の着色抑制効果に優れることがわかる。
Claims (7)
- エチレン構造単位の含有量が異なる2種以上のエチレン-ビニルアルコール系共重合体を有するエチレン-ビニルアルコール系共重合体(A)とソルビン酸エステル(B)と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、
上記エチレン-ビニルアルコール系共重合体(A)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70重量%以上であり、
上記ソルビン酸エステル(B)が、ソルビン酸メチルおよびソルビン酸エチルの少なくとも一方であり、
上記ソルビン酸エステル(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当たり0.00001~1ppm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。 - 上記エチレン構造単位の含有量が異なる2種以上のエチレン-ビニルアルコール系共重合体を有するエチレン-ビニルアルコール系共重合体(A)における、最もエチレン構造単位の含有量が大きいエチレン-ビニルアルコール系共重合体と、最もエチレン構造単位の含有量が小さいエチレン-ビニルアルコール系共重合体とのエチレン構造単位の含有量の差が、2モル%以上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。
- 上記エチレン構造単位の含有量が異なる2種以上のエチレン-ビニルアルコール系共重合体を有するエチレン-ビニルアルコール系共重合体(A)が、エチレン構造単位の含有量が35モル%未満のエチレン-ビニルアルコール系共重合体(A1)と、エチレン構造単位の含有量が35モル%以上のエチレン-ビニルアルコール系共重合体(A2)を少なくとも有することを特徴とする請求項1または2記載のエチレン-ビニルアルコール系共 重合体組成物。
- 上記エチレン構造単位の含有量が35モル%以上のエチレン-ビニルアルコール系共重合体(A2)に対する上記エチレン構造単位の含有量が35モル%未満のエチレン-ビニルアルコール系共重合体(A1)の重量配合比率が、エチレン構造単位の含有量が35モル%未満のエチレン-ビニルアルコール系共重合体(A1)/エチレン構造単位の含有量が35モル%以上のエチレン-ビニルアルコール系共重合体(A2)=1/99~99/1であることを特徴とする請求項3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1~4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溶融成形用材料。
- 請求項1~5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。
- 請求項6記載の多層構造体からなることを特徴とする熱成形容器用材料。
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JPWO2019103073A1 (ja) | 2020-10-01 |
TW201925247A (zh) | 2019-07-01 |
EP3715417A4 (en) | 2020-12-09 |
EP3715417A1 (en) | 2020-09-30 |
EP3715417B1 (en) | 2023-04-26 |
CN111094440A (zh) | 2020-05-01 |
WO2019103073A1 (ja) | 2019-05-31 |
TWI850206B (zh) | 2024-08-01 |
US11161972B2 (en) | 2021-11-02 |
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