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WO2016133040A1 - Procédé de production de film barrière transparent - Google Patents

Procédé de production de film barrière transparent Download PDF

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Publication number
WO2016133040A1
WO2016133040A1 PCT/JP2016/054248 JP2016054248W WO2016133040A1 WO 2016133040 A1 WO2016133040 A1 WO 2016133040A1 JP 2016054248 W JP2016054248 W JP 2016054248W WO 2016133040 A1 WO2016133040 A1 WO 2016133040A1
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WO
WIPO (PCT)
Prior art keywords
organic layer
compound
film
barrier film
layer
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/JP2016/054248
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English (en)
Japanese (ja)
Inventor
清司 伊関
沼田　幸裕
晃侍 伊藤
崇 江畑
稲垣　京子
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Toyobo Co Ltd
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Toyobo Co Ltd
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Filing date
Publication date
Application filed by Toyobo Co Ltd filed Critical Toyobo Co Ltd
Priority to JP2016509161A priority Critical patent/JP6614134B2/ja
Publication of WO2016133040A1 publication Critical patent/WO2016133040A1/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
    • 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
    • B32B27/00—Layered products comprising a layer of synthetic resin
    • B32B27/16—Layered products comprising a layer of synthetic resin specially treated, e.g. irradiated
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B65—CONVEYING; PACKING; STORING; HANDLING THIN OR FILAMENTARY MATERIAL
    • B65D—CONTAINERS FOR STORAGE OR TRANSPORT OF ARTICLES OR MATERIALS, e.g. BAGS, BARRELS, BOTTLES, BOXES, CANS, CARTONS, CRATES, DRUMS, JARS, TANKS, HOPPERS, FORWARDING CONTAINERS; ACCESSORIES, CLOSURES, OR FITTINGS THEREFOR; PACKAGING ELEMENTS; PACKAGES
    • B65D65/00—Wrappers or flexible covers; Packaging materials of special type or form
    • B65D65/38—Packaging materials of special type or form
    • B65D65/40—Applications of laminates for particular packaging purposes
    • 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 method for producing 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 material using an inorganic thin film a material in which a silicon oxide, an aluminum oxide thin film, or the like is laminated is known (for example, see Patent Document 1).
  • the inorganic layer formed on the plastic film is very thin, it may deteriorate when post-processing such as printing on the inorganic thin film layer. For example, in the printing process, due to rubbing with the gravure roll and pigment particles contained in the ink, the inorganic layer may be damaged and the barrier property may be lowered.
  • organic layers can be formed by mixing various materials to improve the adhesion between the inorganic layer and the organic layer, but in a general method using a vacuum process, two or more substances with different evaporation temperatures are mixed. When evaporated, the mixing ratio of the vapor deposition materials and the composition of the deposited film are shifted. Therefore, a flash vapor deposition method in which the material is brought into contact with a heating plate whose temperature has been sufficiently raised from the evaporation temperature of the substance and evaporated instantly is used.
  • a reactive organic substance is flash-deposited, it may be fixed by a heating plate and there may be a problem in stability.
  • stacking without mixing is proposed (for example, refer permission document 3). However, in this method, it is difficult to always make it constant, such as mixing of two layers laminated in a liquid phase. Further, a mechanism for evaporating two kinds of monomers is required, and the apparatus becomes complicated.
  • the present invention solves the above-mentioned problems, and has an excellent barrier property in which an inorganic layer is provided on one surface of a plastic film and an organic layer having excellent adhesion containing a silane coupling agent is laminated thereon.
  • a method for producing a barrier film is provided.
  • 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, wherein the organic layer has at least two kinds of compounds having an acryloyl group and / or a methacryloyl group. And at least one compound of at least two or more compounds having an acryloyl group and / or a methacryloyl group is a silane coupling agent, and the compound is 200 ° C. or more, 300
  • a method for producing a transparent barrier film comprising: forming a liquid organic layer by flash vapor deposition using metallic copper heated to a temperature of not higher than ° C .;
  • the acceleration voltage of the electron beam is preferably 500 V or more and 10 kV or less.
  • an excellent adhesion strength between the organic layer and the inorganic layer is obtained, and a high-performance barrier film is obtained, and the barrier property is deteriorated even after processing such as printing or lamination with another film.
  • a transparent barrier film that can be used as a packaging material that requires high airtightness or a gas barrier material.
  • 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 transparent gas barrier films produced by the production method of the present invention
  • FIGS. 2 and 3 show production apparatuses used in the production method 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 (1) 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 obtained by crosslinking at least two kinds of compounds having an acryloyl group and / or a methacryloyl group. Furthermore, at least one of the compounds needs to be a silane coupling agent. At this time, the weight of the compound of the silane coupling agent is preferably 5% by weight or more based on the total weight of the compound having an acryloyl group or a methacryloyl group.
  • Examples of the compound having an acryloyl group and / or a methacryloyl group include 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 compound which is a silane coupling agent having an acryloyl group and / or a methacryloyl group refers to an organosilicon compound having at least an acryloyl group or a methacryloyl group and a hydrolyzable group. For example, raising 3-methacryloxypropylmethyldimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropylmethyldiethoxysilane, 3-methacryloxypropyltriethoxysilane, 3-acryloxypropyltrimethoxysilane, etc. Can do.
  • These compounds preferably have a viscosity at 20 ° C. of 500 mPa ⁇ s or less from the viewpoint of material supply during vapor deposition. More preferably, it is 200 mPa * s or less. From the viewpoint of safety, the skin primary irritation index (PII) is 2 or less, preferably 1 or less.
  • 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 pigment ink. Further, when the film thickness is 150 nm or more, the protective function is increased, but the distortion is increased and the adhesion is reduced.
  • the flash vapor deposition referred to in the present invention is a method in which a vapor deposition material is brought into contact with a heated plate or the like little by little and instantly evaporated.
  • a material such as a plate to be heated may have only heat resistance, but a metal is preferable from the viewpoint of workability.
  • the heating plate material metal is preferably copper having a purity of at least 90%.
  • a compound having an acryloyl group or a methacryloyl group used in the present invention may be cross-linked by a heating plate, resulting in an increase in molecular weight and difficulty in evaporation.
  • the material that has not evaporated adheres to the surface of the heating plate.
  • the adhering material is polymerized and becomes a solid substance, which cuts off the heat from the heating plate to reduce the evaporation amount and lower the evaporation efficiency.
  • a known technique can be used as a method of heating the heating plate. Examples include a method of installing a heating wire so that thermal contact is good on the opposite surface where the vapor deposition material contacts the heating plate, a method of circulating a heating medium, and a method of heating with an IR heater.
  • the temperature of the heating plate is preferably 200 ° C. or higher for a compound of 500 mPa ⁇ s or less that has fluidity as a liquid supply. High temperature is preferable for flash vapor deposition, but if it is too high, the compound decomposes and is not preferable. Moreover, 300 degrees C or less is preferable from mechanical factors, such as a dimensional change of the heating plate with temperature.
  • a known source can be used as the electron source.
  • the acceleration voltage of electrons is preferably 500 V or higher. If it is 500 V or less, electrons do not sufficiently enter the compound, and radicals necessary for initiation of crosslinking are not sufficiently generated. At an acceleration voltage of 10 kV or more, the number of electrons that pass through the organic layer increases and efficiency decreases. In addition, the generation of X-rays also occurs, causing a problem in safety and health.
  • the transparent vapor deposition barrier film manufacturing method 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).
  • a mixed compound (13) comprising at least two or more kinds of compounds having an acryloyl group and / or a methacryloyl group, and at least one of which is a silane coupling agent, is placed in a liquid container (14).
  • the mixed compound (13) is transferred into the organic vapor deposition source (16) by the liquid pump (15).
  • the transferred mixed 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 and reaches the organic nozzle (9).
  • Adhesive strength of laminate A 40 ⁇ m thick polyethylene film (Toyobo Co., Ltd. L4102) was adhered to a transparent vapor-deposited barrier film using an adhesive for dry lamination (TM590, CAT56 manufactured by Toyo Morton Co., Ltd.) to produce a laminate film did.
  • the adhesive strength of the laminate is measured by cutting the laminate film to a width of 15 mm, peeling a part of the laminate film, using a universal material testing machine (Tensilon), pulling the peel piece at a speed of 300 mm / min, and peeling it 180 °. did.
  • Oxygen permeation amount is measured according to JIS K7126-2 A method by preparing an oxygen permeation amount measuring device (manufactured by OXTRAN 2/21 MOCOM) in an atmosphere of temperature 23 degrees and humidity 65% RH. did.
  • the content ratio wa (%) in the aluminum oxide film and the content ws (%) in the silicon oxide film are Ma (g / cm 2 ) as the adhesion amount per unit area of aluminum oxide, and the unit area of silicon oxide.
  • the amount of adhesion per unit is Mm (g / cm 2 )
  • the following formulas (1) and (2) are obtained.
  • wa 100 ⁇ [Ma / (Ma + Mm)]
  • ws 100-wa
  • the deposition amount per unit area of aluminum oxide is Ma (g / cm 2 )
  • the density of the bulk is ⁇ a (3.97 g / cm 3 )
  • the deposition amount per unit area of silicon oxide is Ms (g / cm 2).
  • the film thickness t (nm) is obtained by the following formula (3).
  • t ((Ma / ( ⁇ a ⁇ 0.8) + Ms / ( ⁇ s ⁇ 0.8)) ⁇ 10 ⁇ 7 ...
  • Formula (3) Several types of inorganic oxide thin films that define the film thickness and composition are prepared and fluorescence is obtained.
  • a calibration curve was prepared by measuring with an X-ray apparatus. Using a fluorescent X-ray analyzer (“ZSX100e” manufactured by Rigaku Corporation), the film thickness composition was measured with a calibration curve prepared in advance. The conditions for the excitation X-ray tube were 50 kV and 70 mA.
  • a cured organic layer is formed in advance with various thicknesses by irradiation with an electron beam comprising a compound having an acryloyl group and / or a methacryloyl group and being a silane coupling agent alone.
  • This organic layer was measured with a fluorescent X-ray analyzer, and a calibration curve was prepared from the fluorescent X-ray intensity of silicon atoms and the thickness of the organic layer consisting of the compound alone as the silane coupling agent.
  • the film thickness of an organic layer obtained by crosslinking and copolymerizing 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 was measured. Further, measurement was performed with fluorescent X-rays, and the equivalent film thickness of the compound having an acryloyl group and / or a methacryloyl group and being a silane coupling agent was calculated from the calibration curve using the value.
  • TEM transmission electron microscope
  • a method of measuring using interference by an ellipsometer can be used.
  • a correlation is obtained with the value obtained by TEM, and the value is converted into the value.
  • the content ratio was calculated by dividing the equivalent film thickness of the compound having an acryloyl group and / or methacryloyl group calculated from the result of fluorescent X-ray and being a silane coupling agent by the total film thickness of the organic layer.
  • an organic layer composed of a compound alone having an acryloyl group and / or a methacryloyl group and a silane coupling agent, a compound having an acryloyl group and / or a methacryloyl group and not a silane coupling agent, and an acryloyl group and / or a methacryloyl group
  • the density of the organic layer crosslinked and copolymerized with the compound that is a silane coupling agent was calculated as the same.
  • Example 1 While a polyethylene terephthalate film (E5100 thickness 12 ⁇ m, manufactured by Toyobo Co., Ltd.) was run as a plastic film at 150 m / min, aluminum oxide and silicon oxide were separately put into a crucible and heated individually with an electron gun for vapor deposition. .
  • the formed inorganic layer had a thickness of 13 nm and an aluminum oxide content of 41% by weight.
  • the formed liquid layer was irradiated with electrons from an electron gun at an acceleration voltage of -8 kV and a current of 400 mA to be crosslinked and cured.
  • the organic film thickness was 77 nm.
  • Table 1 shows the oxygen transmission amount and the laminate strength of the transparent barrier film.
  • Table 2 shows the situation of the heating plate.
  • Example 1 In Example 1, it carried out similarly to Example 1 except heating the copper heating plate to 110 degreeC with the heat medium, and dripping the mixed compound at the speed
  • the state of the heating plate is shown in Table 2.
  • Comparative Example 2 Comparative Example 1 was the same as Comparative Example 1 except that an aluminum heating plate was used. Observe the condition of the heating plate and record it in Table 2.
  • a transparent barrier film having excellent printing resistance and excellent adhesion can be provided.

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

Abstract

La présente invention concerne un film barrière transparent qui a une excellente résistance d'impression et qui comprend une couche inorganique et une couche organique ayant une excellente adhérence et qui est réalisée sous vide. La présente invention concerne un procédé de production d'un film barrière transparent de dépôt par évaporation : le film barrière comprenant une couche inorganique et une couche organique sur au moins une surface d'un film plastique ; la couche organique est fabriquée par réticulation d'au moins deux types de composés comportant chacun un groupe acryloyle ou un groupe méthacryloyle ; au moins un type dudit composé est un agent de couplage au silane ; et le procédé consiste à former la couche organique sur la couche inorganique par dépôt par évaporation flash, le mélange de composé étant évaporé par du cuivre métallique chauffé à une température comprise entre 200°C et 300°C inclus, puis à durcir la couche organique à l'aide de faisceaux électroniques.
PCT/JP2016/054248 2015-02-20 2016-02-15 Procédé de production de film barrière transparent Ceased WO2016133040A1 (fr)

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JP2016509161A JP6614134B2 (ja) 2015-02-20 2016-02-15 透明バリアフィルムの製造法

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JP2015031698 2015-02-20
JP2015-031698 2015-02-20

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WO2016133040A1 true WO2016133040A1 (fr) 2016-08-25

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Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010247335A (ja) * 2009-04-10 2010-11-04 Fujifilm Corp ガスバリアフィルムおよびガスバリアフィルムの製造方法
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
JP2012176519A (ja) * 2011-02-25 2012-09-13 Fujifilm Corp バリア性積層体およびバリア性積層体の製造方法
WO2014103756A1 (fr) * 2012-12-25 2014-07-03 コニカミノルタ株式会社 Film barrière aux gaz
JP2014172231A (ja) * 2013-03-07 2014-09-22 Fujifilm Corp バリア性積層体およびガスバリアフィルム

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010247335A (ja) * 2009-04-10 2010-11-04 Fujifilm Corp ガスバリアフィルムおよびガスバリアフィルムの製造方法
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
JP2012176519A (ja) * 2011-02-25 2012-09-13 Fujifilm Corp バリア性積層体およびバリア性積層体の製造方法
WO2014103756A1 (fr) * 2012-12-25 2014-07-03 コニカミノルタ株式会社 Film barrière aux gaz
JP2014172231A (ja) * 2013-03-07 2014-09-22 Fujifilm Corp バリア性積層体およびガスバリアフィルム

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JPWO2016133040A1 (ja) 2017-11-30

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