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WO2016143461A1 - Procédé de fabrication de film barrière transparent - Google Patents

Procédé de fabrication de film barrière transparent Download PDF

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Publication number
WO2016143461A1
WO2016143461A1 PCT/JP2016/054249 JP2016054249W WO2016143461A1 WO 2016143461 A1 WO2016143461 A1 WO 2016143461A1 JP 2016054249 W JP2016054249 W JP 2016054249W WO 2016143461 A1 WO2016143461 A1 WO 2016143461A1
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WO
WIPO (PCT)
Prior art keywords
compound
layer
organic layer
barrier film
transparent barrier
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Ceased
Application number
PCT/JP2016/054249
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English (en)
Japanese (ja)
Inventor
清司 伊関
晃侍 伊藤
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Toyobo Co Ltd
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Toyobo Co Ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Toyobo Co Ltd filed Critical Toyobo Co Ltd
Priority to JP2016509186A priority Critical patent/JP6938913B2/ja
Publication of WO2016143461A1 publication Critical patent/WO2016143461A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B32—LAYERED PRODUCTS
    • B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B9/00—Layered products comprising a layer of a particular substance not covered by groups B32B11/00 - B32B29/00
    • C—CHEMISTRY; METALLURGY
    • C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
    • C23C—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; SURFACE TREATMENT OF METALLIC MATERIAL BY DIFFUSION INTO THE SURFACE, BY CHEMICAL CONVERSION OR SUBSTITUTION; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL
    • C23C14/00—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material
    • C23C14/06—Coating by vacuum evaporation, by sputtering or by ion implantation of the coating forming material characterised by the coating material
    • C23C14/12—Organic material

Definitions

  • the present invention relates to a transparent barrier film used as a packaging material that requires airtightness such as foods, pharmaceuticals, and electronic parts having excellent gas barrier properties, or a gas barrier material.
  • a film having excellent gas barrier properties a film obtained by laminating an aluminum foil on a plastic film and a film coated with vinylidene chloride or an ethylene vinyl alcohol copolymer are known.
  • a thing using an inorganic thin film what laminated
  • gas barrier properties may be lowered. For example, in the printing process, the inorganic thin film layer may be damaged and the barrier property may be reduced due to rubbing with the gravure roll or pigment particles contained in the printing ink.
  • the present invention solves the above problems, and provides a transparent barrier film having excellent barrier properties in which an inorganic layer is provided on one side of a plastic film and an organic layer is laminated on the inorganic layer with stable quality. It is.
  • the present invention is a method for producing a transparent barrier film having an inorganic layer and an organic layer in this order on at least one side of a plastic film, the compound having an acryloyl group and / or methacryloyl group and the acryloyl group and / or methacryloyl.
  • It is a manufacturing method of the transparent barrier film characterized by including the vacuum evaporation process to form.
  • the vapor pressure of the polymerization inhibitor at 150 ° C. is 2 kPa or less.
  • the polymerization inhibitor is a compound that exhibits a polymerization inhibition effect even in a situation where oxygen does not coexist.
  • the liquid mixture is evaporated by flash vapor deposition to form a liquid organic layer on the surface of the inorganic layer and then cured by electron beam irradiation to form the organic layer.
  • a transparent barrier film having an inorganic layer and an organic layer can be formed efficiently and consistently using a vacuum process. Moreover, it can be formed stably for a long time.
  • the transparent barrier film formed in the present invention can be used as a packaging material or a gas barrier material that requires high airtightness without deterioration of barrier properties even after processing such as printing or laminating with other films. it can.
  • Schematic of transparent barrier film produced by the production method of the present invention Schematic of an example of an apparatus used in the production method of the present invention
  • FIG. 1 shows a laminate of the transparent gas barrier film of the present invention
  • FIGS. 2 and 3 show a manufacturing apparatus as an example.
  • the plastic film (1) referred to in the present invention is a film obtained by melt-extrusion of an organic polymer and stretching, cooling, and heat setting in the longitudinal direction and / or the width direction as necessary.
  • an organic polymer polypropylene, polyethylene terephthalate, polyethylene-2,6-naphthalate, nylon 6, nylon 4, nylon 66, nylon 12, polyvinyl chloride, polyvinylidene chloride, polyvinyl alcohol, wholly aromatic polyamide, polyamideimide, Examples thereof include polyimide, polyetherimide, polysulfone, polyphenylene sulfide, and polyphenylene oxide.
  • organic polymers organic polymers may be copolymerized or blended with a small amount of other organic polymers.
  • known additives such as ultraviolet absorbers, antistatic agents, plasticizers, lubricants, colorants and the like may be added to the organic polymer, and the transparency thereof is not particularly limited.
  • a transparent gas barrier film those having a transmittance of 50% or more are preferred.
  • the plastic film (1) of the present invention is subjected to corona discharge treatment, glow discharge treatment and other surface roughening treatment prior to laminating the thin film layer.
  • a known anchor coat treatment, printing, or decoration may be applied.
  • the thickness of the plastic film (1) in the present invention is preferably in the range of 1 ⁇ m to 300 ⁇ m, more preferably in the range of 9 ⁇ m to 25 ⁇ m.
  • the inorganic layer (2) may be a single layer or a laminate of two or more layers.
  • a particularly preferable inorganic layer (2) is preferably a composite oxide layer prepared by vapor deposition of aluminum oxide and silicon oxide or a composite oxide layer prepared by vapor deposition of aluminum oxide and magnesium oxide.
  • the weight ratio of aluminum oxide contained in the inorganic compound thin film is not particularly limited, but aluminum oxide and silicon oxide (oxidized) contained in the inorganic compound thin film are not limited.
  • the ratio of aluminum oxide is preferably 10% by weight or more, more preferably 20% by weight or more, and further preferably 30% by weight or more with respect to 100% by weight of the total (magnesium).
  • the aluminum oxide ratio is preferably 90% by weight or less, more preferably 75% by weight or less, and further preferably 65% by weight or less. If the ratio of aluminum oxide exceeds 75% by weight, the flexibility tends to be poor, so that cracking due to handling is likely to occur, and stable barrier properties may be difficult to obtain. On the other hand, when the ratio of aluminum oxide is less than 30% by weight, the barrier property tends to be lowered.
  • the film thickness of the inorganic layer (2) of the present invention is not particularly limited, but is preferably 5 to 500 nm, more preferably 8 nm or more and 100 nm or less, and the inorganic layer (2) having a film thickness of less than 5 nm is satisfactory. However, even if the thickness exceeds 500 nm, the corresponding effect of improving the gas barrier property cannot be obtained, which is disadvantageous in terms of bending resistance and manufacturing cost. It becomes.
  • a known method such as a physical vapor deposition method such as a vacuum vapor deposition method, a sputtering method or an ion plating method, a chemical vapor deposition method such as PECVD, or the like is employed.
  • the heating method resistance heating, induction heating, electron beam heating or the like is employed.
  • the organic layer (3) referred to in the present invention is formed by curing a compound having an acryloyl group and / or a methacryloyl group.
  • the compound having an acryloyl group and / or a methacryloyl group may be used alone or in combination of two or more. It is preferable to use at least a compound having an acryloyl group and / or a methacryloyl group and not a silane coupling agent and a compound having an acryloyl group and / or a methacryloyl group and a silane coupling agent.
  • the compound having an acryloyl group and / or a methacryloyl group and not a silane coupling agent is not particularly limited.
  • the silane coupling agent having an acryloyl group and / or a methacryloyl group refers to an organosilicon compound having at least an acryloyl group and / or a methacryloyl group and a hydrolyzable group. For example, raising 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, etc. Can do.
  • the organic layer obtained by cross-linking copolymerization of a compound having an acryloyl group and / or methacryloyl group and not a silane coupling agent and a compound having an acryloyl group and / or methacryloyl group and a silane coupling agent is preferably 5% by weight or more.
  • Silane coupling agent having acryloyl group and / or methacryloyl group with respect to the total weight of the compound having acryloyl group and / or methacryloyl group and not silane coupling agent and compound having acryloyl group and / or methacryloyl group and silane coupling agent The weight ratio of the compound can be calculated by measuring the amount of silicon atoms contained in the organic layer.
  • the compound having an acryloyl group and / or a methacryloyl group and being a silane coupling agent contributes to improving the adhesion between the inorganic layer and the organic layer, but the content is preferably 5% by weight or more. More preferably, it is 10 weight% or more.
  • the content of the compound having an acryloyl group and / or methacryloyl group and being a silane coupling agent increases, the adhesion is improved, but the compound having an acryloyl group and / or methacryloyl group and being a silane coupling agent is expensive and Moreover, since the excess which cannot react at the interface with the inorganic layer also increases, 50% by weight or less is preferable. It is more preferably 40% by weight or less, and most preferably 30% by weight or less.
  • the organic layer has a protective function for the inorganic layer and a function for improving the adhesion when pasted with a sealant and an adhesive.
  • the organic layer is preferably 50 nm or more. If the thickness is 50 nm or less, the inorganic layer cannot be protected from pigment particles contained in the printing ink. Further, when the film thickness is 150 nm or more, the protective function is increased, but the adhesion force is reduced because the stress of the organic layer and the included defects are increased.
  • the polymerization inhibitor in the present invention is a compound that prevents a compound having an acryloyl group and / or a methacryloyl group from being crosslinked by light or heat.
  • Polymerization inhibitors include quinone polymerization inhibitors such as hydroquinone, phenol polymerization inhibitors such as 4-methoxyphenol, nitroso such as phenyl-t-butylnitrone, or nitrone polymerization inhibitors, 4-methoxy-1- Examples thereof include a polymerization inhibitor having a condensed polycyclic aromatic skeleton such as naphthol and 1,4-diethoxynaphthalene (for example, JP 2012-111741 A).
  • the polymerization inhibitor is used by mixing with a compound having an acryloyl group and / or a methacryloyl group.
  • a compound having an acryloyl group and / or a methacryloyl group is heated under vacuum at the time of vapor deposition, It is preferable to use a polymerization inhibitor that exhibits a polymerization inhibiting effect even in a situation where it does not coexist.
  • Polymerization inhibitors that exhibit a polymerization inhibition effect even in the absence of oxygen include polymerization inhibitors having a condensed polycyclic aromatic skeleton such as 4-methoxy-1-naphthol and 1,4-diethoxynaphthalene. Can be mentioned.
  • At least one of the polymerization inhibitors to be used is a polymerization inhibitor having a vapor pressure at 150 ° C. of 2 kPa or less.
  • the polymerization inhibitor having a vapor pressure of 2 kPa or less at 150 ° C. include 4-methoxy-1-naphthol having a condensed polycyclic aromatic skeleton (vapor pressure 0.82 kPa: 175 ° C.), 1,4-diethoxy. There is naphthalene (vapor pressure 1.3 kPa: 175 ° C.).
  • a polymerization inhibitor having a vapor pressure at 150 ° C. higher than 2 kPa evaporates before a compound having an acryloyl group and / or a methacryloyl group when heated at the time of vapor deposition. It is easy to form a gel and solid matter.
  • the addition amount of the polymerization inhibitor referred to in the present invention is preferably 100 ppm or more and 5000 ppm or less with respect to the compound having an acryloyl group and / or a methacryloyl group.
  • concentration 100 ppm or less
  • the compound having an acryloyl group and / or a methacryloyl group is gelled and cured before evaporation. Too much is useless.
  • they are 200 ppm or more and 5000 ppm or less, More preferably, they are 500 ppm or more and 5000 ppm or less, More preferably, they are 800 ppm or more and 5000 ppm.
  • ppm means mg / kg unless otherwise specified.
  • a vapor deposition method which is a vacuum process is suitable.
  • a compound having an acryloyl group and / or a methacryloyl group is placed in a container, heated and evaporated to form a mixed liquid compound layer on the inorganic layer.
  • the compound layer of the mixed liquid is cured by applying an electron beam or ultraviolet rays to form an organic layer.
  • an electron beam or ultraviolet rays it is necessary to add a photopolymerization initiator to the compound.
  • curing with an electron beam is preferred.
  • the vapor deposition method since the compound is maintained in a heated state for a long time, it is necessary to add a large amount of the polymerization inhibitor in the present invention.
  • the vapor deposition method is preferably a flash vapor deposition method in which a compound having an acryloyl group and / or a methacryloyl group is dropped little by little on a sufficiently heated plate or the like and evaporated instantaneously.
  • a flash vapor deposition method when a material in which two or more kinds of compounds are mixed is evaporated, the ratio of each compound at the time of mixing and the ratio of each compound in the mixed liquid formed on the inorganic layer are shifted.
  • flash vapor deposition the deviation is small.
  • it is not necessary to leave the compound which has an acryloyl group and / or a methacryloyl group in the state heated for a long time the point that a gel thing is hard to produce
  • FIGS. 1-10 Schematic diagram of the method for producing a transparent barrier film of the present invention will be described with reference to FIGS.
  • the plastic film roll of the substrate is set on the unwinding roll (4).
  • the unrolled plastic film (1) passes through the plasma processor (5) to treat the surface.
  • the ceramic contained in the crucible (7) is heated and evaporated by the electron gun (6) to form an inorganic layer on the plastic film running on the inorganic coating roll (8).
  • Compound (13) of a mixed liquid of a compound having a acryloyl group and / or methacryloyl group and a polymerization inhibitor is placed in a liquid container (14).
  • the compound (13) is transferred into the organic vapor deposition source (16) by the liquid pump (15).
  • the transferred compound (13) comes into contact with the heating plate (18) heated by the heating wire (17) and becomes steam.
  • the vapor moves in the organic vapor deposition source (16) heated so as not to condense until reaching the organic nozzle (9) and reaches the organic nozzle (9).
  • the vapor of the compound (13) coming out of the heated organic nozzle (9) is deposited on a plastic film in which an inorganic layer running on the organic coating roll (10) is laminated.
  • an organic layer of a mixed liquid compound of a compound having an acryloyl group and / or a methacryloyl group and a polymerization inhibitor is formed on the inorganic layer.
  • the compound layer of the formed mixed liquid is irradiated with an electron beam using an electron beam irradiation device (11) and cured by crosslinking. In this way, an organic layer is formed on the inorganic layer and wound around a winding roll (12).
  • Example 1 A transparent vapor-deposited film (Toyobo Co., Ltd. VE100 thickness 12 ⁇ m) was used as the substrate film.
  • VE100 is obtained by depositing a composite oxide of alumina-silica on a polyethylene terephthalate film.
  • PEG200 # diacrylate produced by Kyoeisha Chemical Co., Ltd., light ester 4EG containing 4-ppm of 4-methoxyphenol as a polymerization inhibitor
  • a polymerization inhibitor 1,4-diethoxynaphthalene produced by Kawasaki Kasei Kogyo Co., Ltd.
  • QS-40 vapor pressure 1.33 kPa (175 ° C.)
  • 0.5 ml of a mixed liquid compound prepared on a copper plate heated to 150 ° C. by a heater was dropped and evaporated to form a liquid phase compound layer on the substrate film.
  • the vacuum chamber was heated to 80 ° C. to reduce the adhesion of the compound. Further, the liquid phase compound layer was irradiated for 10 sec with an electron gun (OME-0202PE manufactured by OMEGATRON Co., Ltd.) with an acceleration voltage of 3 kV and an irradiation current of 2 mA to be cured. After waiting for the temperature of the heating plate to drop, the film was taken out and the thickness of the organic layer was confirmed to be 96 nm. Moreover, although the liquid compound adhered to the heating plate in the vacuum chamber, it could be removed by simple wiping.
  • OME-0202PE manufactured by OMEGATRON Co., Ltd.
  • Example 1 (Comparative Example 1) In Example 1, vapor deposition was carried out in the same manner as in Example 1 except that 1,4-diethoxynaphthalene (Kinopower QS-40, vapor pressure 1.33 kPa (175 ° C.) manufactured by Kawasaki Kasei Kogyo Co., Ltd.) was not added as a polymerization inhibitor. Went. An organic layer having a thickness of 92 nm was formed. There was a gel-like deposit on the heating plate. It did not dissolve in alcohol.

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Mechanical Engineering (AREA)
  • Metallurgy (AREA)
  • Organic Chemistry (AREA)
  • Physical Vapour Deposition (AREA)
  • Laminated Bodies (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

L'invention a pour objet de produire ayant une qualité stable un film barrière transparent qui a une excellente tolérance à l'impression et qui a une couche organique et une couche inorganique qui sont préparées sous vide. À cet effet, l'invention porte sur un procédé pour la fabrication d'un film barrière transparent ayant une couche inorganique et une couche organique dans cet ordre sur au moins une surface d'un film en plastique, caractérisé en ce que ce dernier comprend : une étape de formation d'une couche organique liquide mélangée sur la surface de la couche inorganique à l'aide d'un liquide mélangé comprenant un composé ayant des groupes acryloyle et/ou des groupes méthacryloyle et au moins 50 ppm d'un inhibiteur de polymérisation par rapport audit composé ayant des groupes acryloyle et/ou des groupes méthacryloyle ; et une étape de formation de la couche organique par durcissement de ladite couche organique liquide mélangée.
PCT/JP2016/054249 2015-03-10 2016-02-15 Procédé de fabrication de film barrière transparent Ceased WO2016143461A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
JP2016509186A JP6938913B2 (ja) 2015-03-10 2016-02-15 透明バリアフィルムの製造法

Applications Claiming Priority (4)

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JP2015047210 2015-03-10
JP2015-047210 2015-03-10
JP2015170548 2015-08-31
JP2015-170548 2015-08-31

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WO2016143461A1 true WO2016143461A1 (fr) 2016-09-15

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025134926A1 (fr) * 2023-12-21 2025-06-26 Ｔｏｐｐａｎホールディングス株式会社 Procédé de production d'un film barrière aux gaz, film barrière aux gaz, film de matériau d'emballage, et matériau d'emballage

Citations (7)

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US6040017A (en) * 1998-10-02 2000-03-21 Sigma Laboratories, Inc. Formation of multilayered photonic polymer composites
JP2006095932A (ja) * 2004-09-30 2006-04-13 Toppan Printing Co Ltd 積層体の製造方法
JP2007113043A (ja) * 2005-10-19 2007-05-10 Konica Minolta Holdings Inc ガスバリア性薄膜積層体、ガスバリア性樹脂基材とそれを用いた有機エレクトロルミネッセンスデバイス
JP2009071301A (ja) * 2007-09-11 2009-04-02 Asm Japan Kk プラズマｃｖｄ装置を用いて炭素重合体膜を形成する方法
JP2012111741A (ja) * 2010-11-06 2012-06-14 Kawasaki Kasei Chem Ltd 縮合多環芳香族骨格を有する重合禁止剤及びその組成物
JP2014143195A (ja) * 2012-12-27 2014-08-07 Sekisui Chem Co Ltd 有機薄膜素子保護用蒸着材料、樹脂保護膜、及び、有機光デバイス
JP2014521839A (ja) * 2011-08-05 2014-08-28 スリーエム イノベイティブ プロパティズ カンパニー 蒸気を処理するためのシステム及び方法

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ATE218398T1 (de) * 1993-10-04 2002-06-15 3M Innovative Properties Co Verfahren zur herstellung einer acrylatbeschichtung
US5440446A (en) * 1993-10-04 1995-08-08 Catalina Coatings, Inc. Acrylate coating material
JP2010247369A (ja) * 2009-04-13 2010-11-04 Fujifilm Corp ガスバリア積層体の製造方法およびガスバリア積層体

Patent Citations (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6040017A (en) * 1998-10-02 2000-03-21 Sigma Laboratories, Inc. Formation of multilayered photonic polymer composites
JP2006095932A (ja) * 2004-09-30 2006-04-13 Toppan Printing Co Ltd 積層体の製造方法
JP2007113043A (ja) * 2005-10-19 2007-05-10 Konica Minolta Holdings Inc ガスバリア性薄膜積層体、ガスバリア性樹脂基材とそれを用いた有機エレクトロルミネッセンスデバイス
JP2009071301A (ja) * 2007-09-11 2009-04-02 Asm Japan Kk プラズマｃｖｄ装置を用いて炭素重合体膜を形成する方法
JP2012111741A (ja) * 2010-11-06 2012-06-14 Kawasaki Kasei Chem Ltd 縮合多環芳香族骨格を有する重合禁止剤及びその組成物
JP2014521839A (ja) * 2011-08-05 2014-08-28 スリーエム イノベイティブ プロパティズ カンパニー 蒸気を処理するためのシステム及び方法
JP2014143195A (ja) * 2012-12-27 2014-08-07 Sekisui Chem Co Ltd 有機薄膜素子保護用蒸着材料、樹脂保護膜、及び、有機光デバイス

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2025134926A1 (fr) * 2023-12-21 2025-06-26 Ｔｏｐｐａｎホールディングス株式会社 Procédé de production d'un film barrière aux gaz, film barrière aux gaz, film de matériau d'emballage, et matériau d'emballage

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