JP6753315B2 - エチレン−ビニルアルコール系共重合体組成物、ペレット、多層構造体およびエチレン−ビニルアルコール系共重合体組成物の製造方法 - 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、多層構造体およびエチレン−ビニルアルコール系共重合体組成物の製造方法 Download PDFInfo
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- JP6753315B2 JP6753315B2 JP2016575984A JP2016575984A JP6753315B2 JP 6753315 B2 JP6753315 B2 JP 6753315B2 JP 2016575984 A JP2016575984 A JP 2016575984A JP 2016575984 A JP2016575984 A JP 2016575984A JP 6753315 B2 JP6753315 B2 JP 6753315B2
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- Prior art keywords
- ethylene
- evoh resin
- resin composition
- vinyl alcohol
- based copolymer
- Prior art date
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- 229920000219 Ethylene vinyl alcohol Polymers 0.000 title claims description 155
- 239000008188 pellet Substances 0.000 title claims description 44
- 239000000203 mixture Substances 0.000 title claims description 20
- 238000004519 manufacturing process Methods 0.000 title claims description 18
- 239000004715 ethylene vinyl alcohol Substances 0.000 claims description 152
- 229920001577 copolymer Polymers 0.000 claims description 43
- 150000002506 iron compounds Chemical class 0.000 claims description 36
- 229920001567 vinyl ester resin Polymers 0.000 claims description 35
- 239000003505 polymerization initiator Substances 0.000 claims description 22
- RZXDTJIXPSCHCI-UHFFFAOYSA-N hexa-1,5-diene-2,5-diol Chemical compound OC(=C)CCC(O)=C RZXDTJIXPSCHCI-UHFFFAOYSA-N 0.000 claims description 17
- 229910052751 metal Inorganic materials 0.000 claims description 13
- 239000002184 metal Substances 0.000 claims description 13
- 150000002894 organic compounds Chemical class 0.000 claims description 13
- 238000007127 saponification reaction Methods 0.000 claims description 13
- IMROMDMJAWUWLK-UHFFFAOYSA-N Ethenol Chemical compound OC=C IMROMDMJAWUWLK-UHFFFAOYSA-N 0.000 claims 1
- UFRKOOWSQGXVKV-UHFFFAOYSA-N ethene;ethenol Chemical compound C=C.OC=C UFRKOOWSQGXVKV-UHFFFAOYSA-N 0.000 description 135
- 239000011342 resin composition Substances 0.000 description 105
- 229920005989 resin Polymers 0.000 description 70
- 239000011347 resin Substances 0.000 description 70
- 239000010410 layer Substances 0.000 description 50
- 238000000034 method Methods 0.000 description 41
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
- 238000006116 polymerization reaction Methods 0.000 description 32
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 30
- 241000251468 Actinopterygii Species 0.000 description 19
- 239000002585 base Substances 0.000 description 18
- 239000000243 solution Substances 0.000 description 17
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 16
- -1 and has transparency Substances 0.000 description 16
- 229920005672 polyolefin resin Polymers 0.000 description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
- 239000000178 monomer Substances 0.000 description 15
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 13
- 239000005977 Ethylene Substances 0.000 description 13
- 238000000465 moulding Methods 0.000 description 13
- 239000004840 adhesive resin Substances 0.000 description 12
- 229920006223 adhesive resin Polymers 0.000 description 12
- 239000002904 solvent Substances 0.000 description 12
- 238000001035 drying Methods 0.000 description 11
- 239000005022 packaging material Substances 0.000 description 10
- 239000007789 gas Substances 0.000 description 9
- 229910052742 iron Inorganic materials 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
- 239000004711 α-olefin Substances 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 239000000463 material Substances 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- 238000000071 blow moulding Methods 0.000 description 6
- 229920005992 thermoplastic resin Polymers 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 239000004743 Polypropylene Substances 0.000 description 5
- 230000004888 barrier function Effects 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 230000001112 coagulating effect Effects 0.000 description 5
- 230000015271 coagulation Effects 0.000 description 5
- 238000005345 coagulation Methods 0.000 description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 5
- 229920001155 polypropylene Polymers 0.000 description 5
- 229910001220 stainless steel Inorganic materials 0.000 description 5
- 239000010935 stainless steel Substances 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 230000006866 deterioration Effects 0.000 description 4
- 238000001125 extrusion Methods 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000012943 hotmelt Substances 0.000 description 4
- 238000010030 laminating Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 4
- 229910052697 platinum Inorganic materials 0.000 description 4
- 125000003367 polycyclic group Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- UPZFLZYXYGBAPL-UHFFFAOYSA-N 2-ethyl-2-methyl-1,3-dioxolane Chemical compound CCC1(C)OCCO1 UPZFLZYXYGBAPL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000003814 drug Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 238000000605 extraction Methods 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 229910000398 iron phosphate Inorganic materials 0.000 description 3
- WBJZTOZJJYAKHQ-UHFFFAOYSA-K iron(3+) phosphate Chemical compound [Fe+3].[O-]P([O-])([O-])=O WBJZTOZJJYAKHQ-UHFFFAOYSA-K 0.000 description 3
- 239000011259 mixed solution Substances 0.000 description 3
- 150000001451 organic peroxides Chemical class 0.000 description 3
- 229920000098 polyolefin Polymers 0.000 description 3
- 229920006124 polyolefin elastomer Polymers 0.000 description 3
- 239000002356 single layer Substances 0.000 description 3
- 230000003068 static effect Effects 0.000 description 3
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 3
- WKEWCYHGACEYTR-UHFFFAOYSA-N tert-butyl decaneperoxoate Chemical compound CCCCCCCCCC(=O)OOC(C)(C)C WKEWCYHGACEYTR-UHFFFAOYSA-N 0.000 description 3
- 229920006163 vinyl copolymer Polymers 0.000 description 3
- JFFYKITVXPZLQS-UHFFFAOYSA-N 2-methylidenepropane-1,3-diol Chemical compound OCC(=C)CO JFFYKITVXPZLQS-UHFFFAOYSA-N 0.000 description 2
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- VQTUBCCKSQIDNK-UHFFFAOYSA-N Isobutene Chemical compound CC(C)=C VQTUBCCKSQIDNK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 125000005907 alkyl ester group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 238000005520 cutting process Methods 0.000 description 2
- 229920005676 ethylene-propylene block copolymer Polymers 0.000 description 2
- 235000013305 food Nutrition 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 239000003999 initiator Substances 0.000 description 2
- 239000000155 melt Substances 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 2
- BWJUFXUULUEGMA-UHFFFAOYSA-N propan-2-yl propan-2-yloxycarbonyloxy carbonate Chemical compound CC(C)OC(=O)OOC(=O)OC(C)C BWJUFXUULUEGMA-UHFFFAOYSA-N 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
- 239000012086 standard solution Substances 0.000 description 2
- OPQYOFWUFGEMRZ-UHFFFAOYSA-N tert-butyl 2,2-dimethylpropaneperoxoate Chemical compound CC(C)(C)OOC(=O)C(C)(C)C OPQYOFWUFGEMRZ-UHFFFAOYSA-N 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- STEKLRLQGZCGKC-UHFFFAOYSA-N (4-tert-butylcyclohexyl) (4-tert-butylcyclohexyl)oxycarbonyloxyperoxy carbonate Chemical compound C1CC(C(C)(C)C)CCC1OC(=O)OOOOC(=O)OC1CCC(C(C)(C)C)CC1 STEKLRLQGZCGKC-UHFFFAOYSA-N 0.000 description 1
- BEQKKZICTDFVMG-UHFFFAOYSA-N 1,2,3,4,6-pentaoxepane-5,7-dione Chemical compound O=C1OOOOC(=O)O1 BEQKKZICTDFVMG-UHFFFAOYSA-N 0.000 description 1
- NWUYHJFMYQTDRP-UHFFFAOYSA-N 1,2-bis(ethenyl)benzene;1-ethenyl-2-ethylbenzene;styrene Chemical compound C=CC1=CC=CC=C1.CCC1=CC=CC=C1C=C.C=CC1=CC=CC=C1C=C NWUYHJFMYQTDRP-UHFFFAOYSA-N 0.000 description 1
- 125000000424 1,2-diol group Chemical group 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
- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 1
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical compound CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 description 1
- SCFWAOWWAANBPY-UHFFFAOYSA-N 2,2-dimethyl-3-butenoic acid Chemical compound C=CC(C)(C)C(O)=O SCFWAOWWAANBPY-UHFFFAOYSA-N 0.000 description 1
- CRJIYMRJTJWVLU-UHFFFAOYSA-N 2,4,4-trimethylpentan-2-yl 3-(5,5-dimethylhexyl)dioxirane-3-carboxylate Chemical compound CC(C)(C)CCCCC1(C(=O)OC(C)(C)CC(C)(C)C)OO1 CRJIYMRJTJWVLU-UHFFFAOYSA-N 0.000 description 1
- FKAKGSJLTBVQOP-UHFFFAOYSA-N 2-(acetyloxymethyl)prop-2-enyl acetate Chemical compound CC(=O)OCC(=C)COC(C)=O FKAKGSJLTBVQOP-UHFFFAOYSA-N 0.000 description 1
- DIBCJRYCOGXPAM-UHFFFAOYSA-N 2-(propanoyloxymethyl)prop-2-enyl propanoate Chemical compound CCC(=O)OCC(=C)COC(=O)CC DIBCJRYCOGXPAM-UHFFFAOYSA-N 0.000 description 1
- PFHOSZAOXCYAGJ-UHFFFAOYSA-N 2-[(2-cyano-4-methoxy-4-methylpentan-2-yl)diazenyl]-4-methoxy-2,4-dimethylpentanenitrile Chemical compound COC(C)(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)(C)OC PFHOSZAOXCYAGJ-UHFFFAOYSA-N 0.000 description 1
- WYGWHHGCAGTUCH-UHFFFAOYSA-N 2-[(2-cyano-4-methylpentan-2-yl)diazenyl]-2,4-dimethylpentanenitrile Chemical compound CC(C)CC(C)(C#N)N=NC(C)(C#N)CC(C)C WYGWHHGCAGTUCH-UHFFFAOYSA-N 0.000 description 1
- TVWBTVJBDFTVOW-UHFFFAOYSA-N 2-methyl-1-(2-methylpropylperoxy)propane Chemical compound CC(C)COOCC(C)C TVWBTVJBDFTVOW-UHFFFAOYSA-N 0.000 description 1
- RTEZVHMDMFEURJ-UHFFFAOYSA-N 2-methylpentan-2-yl 2,2-dimethylpropaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)C(C)(C)C RTEZVHMDMFEURJ-UHFFFAOYSA-N 0.000 description 1
- YMMLZUQDXYPNOG-UHFFFAOYSA-N 2-methylpentan-2-yl 7,7-dimethyloctaneperoxoate Chemical compound CCCC(C)(C)OOC(=O)CCCCCC(C)(C)C YMMLZUQDXYPNOG-UHFFFAOYSA-N 0.000 description 1
- JUJHZOVDCJJUJK-UHFFFAOYSA-N 3-methylidenepentane-1,5-diol Chemical compound OCCC(=C)CCO JUJHZOVDCJJUJK-UHFFFAOYSA-N 0.000 description 1
- 229920000178 Acrylic resin Polymers 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004709 Chlorinated polyethylene Substances 0.000 description 1
- 239000004278 EU approved seasoning Substances 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 229910021578 Iron(III) chloride Inorganic materials 0.000 description 1
- 240000008415 Lactuca sativa Species 0.000 description 1
- 244000294411 Mirabilis expansa Species 0.000 description 1
- 235000015429 Mirabilis expansa Nutrition 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 229920001328 Polyvinylidene chloride Polymers 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 150000001242 acetic acid derivatives Chemical class 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000001339 alkali metal compounds Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- RZJRJXONCZWCBN-UHFFFAOYSA-N alpha-octadecene Natural products CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000002216 antistatic agent Substances 0.000 description 1
- 229910052786 argon Inorganic materials 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 235000013361 beverage Nutrition 0.000 description 1
- 238000007664 blowing Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 238000012662 bulk polymerization Methods 0.000 description 1
- ITMIAZBRRZANGB-UHFFFAOYSA-N but-3-ene-1,2-diol Chemical compound OCC(O)C=C ITMIAZBRRZANGB-UHFFFAOYSA-N 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical class C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- NSGQRLUGQNBHLD-UHFFFAOYSA-N butan-2-yl butan-2-yloxycarbonyloxy carbonate Chemical compound CCC(C)OC(=O)OOC(=O)OC(C)CC NSGQRLUGQNBHLD-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000013522 chelant Substances 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000004040 coloring Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000013329 compounding Methods 0.000 description 1
- 230000006835 compression Effects 0.000 description 1
- 238000007906 compression Methods 0.000 description 1
- 238000011437 continuous method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000011162 core material Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 239000003431 cross linking reagent Substances 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 239000012933 diacyl peroxide Substances 0.000 description 1
- 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
- 229910001873 dinitrogen Inorganic materials 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 235000015071 dressings Nutrition 0.000 description 1
- 238000007720 emulsion polymerization reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- YCUBDDIKWLELPD-UHFFFAOYSA-N ethenyl 2,2-dimethylpropanoate Chemical compound CC(C)(C)C(=O)OC=C YCUBDDIKWLELPD-UHFFFAOYSA-N 0.000 description 1
- MEGHWIAOTJPCHQ-UHFFFAOYSA-N ethenyl butanoate Chemical compound CCCC(=O)OC=C MEGHWIAOTJPCHQ-UHFFFAOYSA-N 0.000 description 1
- CMDXMIHZUJPRHG-UHFFFAOYSA-N ethenyl decanoate Chemical compound CCCCCCCCCC(=O)OC=C CMDXMIHZUJPRHG-UHFFFAOYSA-N 0.000 description 1
- GLVVKKSPKXTQRB-UHFFFAOYSA-N ethenyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)OC=C GLVVKKSPKXTQRB-UHFFFAOYSA-N 0.000 description 1
- GFJVXXWOPWLRNU-UHFFFAOYSA-N ethenyl formate Chemical compound C=COC=O GFJVXXWOPWLRNU-UHFFFAOYSA-N 0.000 description 1
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 1
- BLZSRIYYOIZLJL-UHFFFAOYSA-N ethenyl pentanoate Chemical compound CCCCC(=O)OC=C BLZSRIYYOIZLJL-UHFFFAOYSA-N 0.000 description 1
- UIWXSTHGICQLQT-UHFFFAOYSA-N ethenyl propanoate Chemical compound CCC(=O)OC=C UIWXSTHGICQLQT-UHFFFAOYSA-N 0.000 description 1
- 229920006242 ethylene acrylic acid copolymer Polymers 0.000 description 1
- 239000005038 ethylene vinyl acetate Substances 0.000 description 1
- 229920006226 ethylene-acrylic acid Polymers 0.000 description 1
- 229920006244 ethylene-ethyl acrylate Polymers 0.000 description 1
- 238000010101 extrusion blow moulding Methods 0.000 description 1
- 235000021107 fermented food Nutrition 0.000 description 1
- 229960004887 ferric hydroxide Drugs 0.000 description 1
- 229960002089 ferrous chloride Drugs 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000006260 foam Substances 0.000 description 1
- 239000005003 food packaging material Substances 0.000 description 1
- 235000011194 food seasoning agent Nutrition 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000000499 gel Substances 0.000 description 1
- 239000001307 helium Substances 0.000 description 1
- 229910052734 helium Inorganic materials 0.000 description 1
- SWQJXJOGLNCZEY-UHFFFAOYSA-N helium atom Chemical compound [He] SWQJXJOGLNCZEY-UHFFFAOYSA-N 0.000 description 1
- 229920001903 high density polyethylene Polymers 0.000 description 1
- 239000004700 high-density polyethylene Substances 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 239000003317 industrial substance Substances 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000001802 infusion Methods 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000010102 injection blow moulding Methods 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000003456 ion exchange resin Substances 0.000 description 1
- 229920003303 ion-exchange polymer Polymers 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- 150000002505 iron Chemical class 0.000 description 1
- NMCUIPGRVMDVDB-UHFFFAOYSA-L iron dichloride Chemical compound Cl[Fe]Cl NMCUIPGRVMDVDB-UHFFFAOYSA-L 0.000 description 1
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N iron oxide Inorganic materials [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 1
- 229910000358 iron sulfate Inorganic materials 0.000 description 1
- RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
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Description
なお、かかる鉄化合物が上記のようにEVOH樹脂に含有される詳細な理由は不明であるが、低温での活性が高い有機化合物を重合開始剤として用い、かつステンレス鋼製のコラム弁を有するポンプを用いる場合に、かかるコラム弁より溶出し不可避的に含有されるものと推測される。
本発明は、かかる特定の重合開始剤を用いて得られたEVOH樹脂組成物において、その鉄化合物の含有量を、EVOH樹脂組成物の重量あたり、金属換算にて0.001〜2ppmとすることで、熱溶融成形物中の微小フィッシュアイの低減が可能となることを見出した。
以下、詳細に説明する。
かかるEVOH樹脂の製造法について、順を追って説明する。
本発明のEVOH樹脂組成物の製造では、まず、エチレンとビニルエステル系モノマーを、重合溶媒中、特定の重合開始剤の存在下で重合(反応)させてエチレン−ビニルエステル系共重合体を得る。
その他の重合法として、例えば、懸濁重合、エマルジョン重合、バルク重合などを挙げることができるが、工業的には溶液重合が用いられる。また、重合方式は、連続式、回分式のいずれであってもよい。
重合溶媒の使用量は、目的とする共重合体の重合度に合わせて、重合溶媒の連鎖移動定数を考慮して適宜選択すればよく、例えば、重合溶媒がメタノールの時は、S(重合溶媒)/M(モノマー)=0.01〜10(重量比)、好ましくは0.05〜7(重量比)程度の範囲から選択される。
このようにして得られたエチレン−ビニルエステル共重合体は、必要に応じて、未反応のビニルエステル系モノマーが除去された後、次いでケン化することで、エチレン−ビニルエステル系共重合体のケン化物すなわち、EVOH樹脂が得られる。
なお、上記未反応のビニルエステル系モノマーの除去により、残存ビニルエステル系モノマーの含有量を0.1重量%以下、さらには0.05重量%以下にすることが好ましい。
また、不均一ケン化の際は、必要に応じてアセトン、ヒドラジン、長鎖のアルキルアミン類等を着色防止のため配合しても良い。
かかるMFRの調整にあたっては、EVOH樹脂の重合度を調整すればよく、さらには架橋剤や可塑剤を添加して調整することも可能である。
本発明のEVOH樹脂組成物は、鉄化合物の含有量がEVOH樹脂組成物の重量あたり、金属換算にて0.001〜2ppmであることを特徴とするものである。かかる鉄化合物の含有量は、金属換算にて好ましくは0.01〜1.5ppm、特に0.1〜1ppm、殊に0.2〜0.6ppmであり、鉄化合物の含有量が多すぎると熱溶融成形物中の微小フィッシュアイの量が増加する傾向がある。
中でも、工程が簡便であることから、通常は(i)の方法が用いられる。
かかる多孔性EVOH樹脂含水ペレットは、抽剤に接触させる工程において、EVOH樹脂中の鉄化合物の溶出を効率的に行うことができる。
EVOH樹脂組成物ペレットを電子天秤にて秤量(W1)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分間放冷後の重量を秤量(W2)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樹脂組成物を含む層を少なくとも1層有するものである。本発明のEVOH樹脂組成物を含む層(以下、単に「樹脂組成物層」という)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、基材に用いられる樹脂を「基材樹脂」と略記することがある。)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。
上記の層構成において、それぞれの層間には、必要に応じて接着性樹脂を含有する接着性樹脂層を介層してもよい。
また、本発明の樹脂組成物から得られた多層延伸フィルムをシュリンク用フィルムとして用いる場合には、熱収縮性を付与するために、上記の熱固定を行わず、例えば延伸後のフィルムに冷風を当てて冷却固定するなどの処理を行えばよい。
特に、本発明のEVOH樹脂組成物を含有する層は、微小フィッシュアイの量が極めて少ないため、高度な透明性が要求される医薬品用の包装材料(例えば、輸液用バッグ)として特に有用である。
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。
重合開始剤としてt−ブチルパーオキシデカノエート(60℃での半減期時間100分間)を用い、系内にステンレス鋼製のコラム弁を有するポンプを有する装置を用いて得られたエチレン−酢酸ビニル共重合体をケン化して得られたEVOH樹脂〔エチレン構造単位の含有量29モル%、ケン化度99.7モル%、MFR8g/10分(210℃、荷重2160g)〕の水/メタノール溶液(水/メタノール=40/60(重量比)、EVOH樹脂分36重量%)を得た。かかる溶液を、孔を有するダイスから凝固浴中にストランド状に押出して凝固させ、かかるストランドをカッターで切断して含水ペレット(水分量60%)を得た。かかる含水ペレットを、予めリン酸化合物にて処理し鉄化合物をリン酸鉄として析出除去した水中に、浴比(抽剤/含水ペレット:重量比)2、30℃で240分間浸漬し、これを120℃の熱風乾燥器中に10時間静置し、EVOH樹脂組成物ペレットを得た。
押出機:直径(D)40mm、L/D=28
スクリュ:フルフライトタイプ 圧縮比=3.5
スクリーンパック:90/120/90メッシュ
ダイ:幅450mm、コートハンガータイプ
設定温度:C1/C2/C3/C4/A/D=190/210/230/230/220/220℃
スクリュ回転数:10rpm
引取速度:3m/分
ロール温度:80℃
結果を下記表1に示す。
重合開始剤としてt−ブチルパーオキシデカノエート(60℃での半減期時間100分間)を用い、系内にステンレス鋼製のコラム弁を有するポンプを有する装置を用いて得られたエチレン−酢酸ビニル共重合体をケン化して得られたEVOH樹脂〔エチレン構造単位の含有量32モル%、ケン化度99.7モル%、MFR12g/10分(210℃、荷重2160g)〕の水/メタノール溶液(水/メタノール=35/65(重量比)、EVOH樹脂分39重量%)を得た。かかる溶液を、孔を有するダイスから凝固浴中にストランド状に押出して凝固させ、かかるストランドをカッターで切断して含水ペレット(水分量58%)を得た。かかる含水ペレットを、予めリン酸化合物にて処理し鉄化合物をリン酸鉄として析出除去した水中に、浴比(抽剤/含水ペレット:重量比)2、30℃で240分間浸漬し、これを120℃の熱風乾燥器中に10時間静置し、EVOH樹脂組成物ペレットを得た。得られたEVOH樹脂組成物ペレットを、実施例1と同様に単層フィルムとして評価した。
結果を下記表1に示す。
重合開始剤としてt−ブチルパーオキシデカノエート(60℃での半減期時間100分間)を用い、系内にステンレス鋼製のコラム弁を有するポンプを有する装置を用いて得られたエチレン−酢酸ビニル共重合体をケン化して得られたEVOH樹脂〔エチレン構造単位の含有量44モル%、ケン化度99.7モル%、MFR12g/10分(210℃、荷重2160g)〕の水/メタノール溶液(水/メタノール=20/80(重量比)、EVOH樹脂分36重量%)を得た。かかる溶液を、孔を有するダイスから凝固浴中にストランド状に押出して凝固させ、かかるストランドをカッターで切断して含水ペレット(水分量60%)を得た。かかる含水ペレットを、リン酸化合物処理を施していない水中に、浴比(抽剤/含水ペレット:重量比)2、30℃で240分間浸漬し、これを118℃の熱風乾燥器中に10時間静置し、EVOH樹脂組成物ペレットを得た。得られたEVOH樹脂組成物ペレットを、実施例1と同様に単層フィルムとして評価した。
結果を下記表1に示す。
Claims (5)
- エチレン−ビニルアルコール系共重合体と鉄化合物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が、重合開始剤として60℃での半減期が10〜300分間である有機化合物を用いたエチレン−ビニルエステル共重合体のケン化物であり、
上記鉄化合物の含有量がエチレン−ビニルアルコール共重合体組成物の重量あたり金属換算にて0.001〜2ppm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。 - 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からなることを特徴とするペレット。
- 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を含有する層を少なくとも1層有することを特徴とする多層構造体。
- 有機化合物を重合開始剤としてエチレン−ビニルエステル系共重合体を得る工程、当該エチレン−ビニルエステル系共重合体をケン化してエチレン−ビニルアルコール系共重合体を得る工程、および当該エチレン−ビニルアルコール系共重合体の鉄化合物の含有量を調整し、エチレン−ビニルアルコール系共重合体組成物を得る工程を備えるエチレン−ビニルアルコール系共重合体組成物の製造方法であって、
上記有機化合物が、60℃での半減期が10〜300分間であり、
上記エチレン−ビニルアルコール系共重合体組成物の鉄化合物の含有量が、当該エチレン−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0.001〜2ppm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の製造方法。 - 上記エチレン−ビニルアルコール系共重合体の鉄化合物の含有量を調整し、エチレン−ビニルアルコール系共重合体組成物を得る工程の調整が、エチレン−ビニルアルコール系共重合体を、抽剤に接触させることを特徴とする請求項4記載のエチレン−ビニルアルコール系共重合体組成物の製造方法。
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