WO1998034982A1 - Primer for plastic films - Google Patents
Primer for plastic films Download PDFInfo
- Publication number
- WO1998034982A1 WO1998034982A1 PCT/US1998/002498 US9802498W WO9834982A1 WO 1998034982 A1 WO1998034982 A1 WO 1998034982A1 US 9802498 W US9802498 W US 9802498W WO 9834982 A1 WO9834982 A1 WO 9834982A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- primer
- poly
- vinyl alcohol
- layer
- films
- Prior art date
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/16—Nitrogen-containing compounds
- C08K5/17—Amines; Quaternary ammonium compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/07—Aldehydes; Ketones
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D129/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an alcohol, ether, aldehydo, ketonic, acetal, or ketal radical; Coating compositions based on hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Coating compositions based on derivatives of such polymers
- C09D129/02—Homopolymers or copolymers of unsaturated alcohols
- C09D129/04—Polyvinyl alcohol; Partially hydrolysed homopolymers or copolymers of esters of unsaturated alcohols with saturated carboxylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
Definitions
- the invention relates to a primer for plastic films which comprises a blend of poly(vinyl alcohol) and an adhesion promoter, specifically poly(ethylene imine) and/or a hardened epoxy resin.
- the invention provides plastic films with excellent oxygen- barrier properties.
- poly(vinyl alcohol) is a water-soluble synthetic polymer made by alcoholysis of polyvinyl acetate. Among other things, it is known for utility as a laminating adhesive. When used in packaging films, poly(vinyl alcohol) has been described as providing a film which is impervious to oils, fats and waxes and to be an excellent oxygen barrier. For this reason, poly(vinyl alcohol) is often used as barrier coatings on thermoplastic films. No single unmodified polymeric film, however, has the gas and moisture barrier characteristics and adhesion property needed for packaging.
- the multilayer film of Knoerzer et al. includes a polymeric substrate having a primer coating on at least one surface of the substrate, a layer of cross-linked poly(vinyl alcohol) on the coating, and a layer of a blend of a poly(vinyl alcohol) homopolymer or copolymer and an ethylene acrylic acid copolymer on the cross-linked layer.
- This reference also discloses that an optional metal layer can be deposited on the blend layer.
- U.S. Patent No. 4,214,039 to Steiner et al. is directed to thermoplastic films which include a film substrate having a primer coating layer applied to it, and a vinylidene chloride polymer as a top coat applied on the primer coating layer.
- These films require two separate layers of primer and polymer in order to obtain both chemical barrier and adhesion properties.
- Many coaters only have two stations for applying coating to one side of a film at a time.
- the present invention relates to a primer for plastic films and the use of the primer in packaging materials.
- the primer includes a blend of poly( vinyl alcohol) and an adhesion promoter, specifically poly(ethylene imine) and/or a hardened epoxy resin.
- the invention is useful to improve the oxygen-barrier properties of a plastic film.
- the hardened epoxy resin is in an amount of about 15 to about 35 parts per hundred poly(vinyl alcohol).
- the primer can further include an glyoxal in an amount of about 10 to about 20 parts per hundred poly(vinyl alcohol).
- the primer can further include choline chloride.
- the adhesion promoter is preferably polyethyleneimine.
- the packaging material of the present invention includes (a) a packaging substrate that has a first surface layer and a second surface layer; (b) a precoating layer having a primer coated on at least one surface layer of the substrate, wherein the primer is a blend of poly( vinyl alcohol), an adhesion promoter and/or an epoxy resin; and (c) optionally a top coat layer and/or a metallic layer deposited thereon the precoating layer.
- packaging films having a unique primer layer are produced.
- the unique blend of the primer layer of the present invention provides excellent oxygen barrier properties.
- the primer layers of the present invention can have a coating layer and/or a metallic layer deposited thereon, and thus offer greater barrier properties and sealant strength. For example, an unexpected synergy between the primer and top coats provides additional barrier enhancement.
- Figure 1 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties of the uncoated film
- Figure 2 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties for the coated films
- Figure 3 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties for the metallized film.
- Figure 4 is a plot showing the concentration of primer ingredients vs. crimp-seal strength for coated films for seals formed at 127° C; and Figure 5 is another plot showing the concentration of primer ingredients vs. crimp-seal strength for coated films for seals formed at about 104°C.
- the invention comprises a primer for plastic film and the use of the primer in packaging materials.
- the primer is a blend of poly (vinyl alcohol) and an adhesion promoter and/or a hardened epoxy resin.
- the primer of the invention can be used as a primer layer for coatings and/or metallization of a substrate such as oriented polypropylene or other plastic film.
- the primed and coated or primed and metallized film has enhanced oxygen barrier properties. Synergistic oxygen barrier properties have been found in that the barrier properties are better than expected based on the oxygen barrier contribution of the individual layers.
- the poly(vinyl alcohol) in the blend of the present invention refers to any commercially available poly(vinyl alcohol), e.g., ENANOL 71-30, an E.I. DuPont product.
- adhesion promoter examples include, but are not limited to,hardened epoxy as described by U.S. Patent No. 4,214,039 to Steiner which is incorporated herein by refernce and polyethyleneimine, in which polyethyleneimine is preferred.
- the amount of the epoxy resin can range from between about 15 and about 35 parts per hundred parts poly( vinyl alcohol). Higher epoxy levels are found to degrade barrier properties, 25 parts per hundred parts poly(vinyl alcohol) result in good oxygen barrier properties.
- the primer coating can further contain a cross-linking agent in an amount ranging from about 10 and 20 parts per hundred parts poly(vinyl alcohol). A higher level is useful to promote cross-linking of the PNOH primer.
- Suitable examples of the cross-linking agent in the present invention include, but are not limited to, glyoxal, melamine formaldehyde, glutaraldehyde, with glyoxal being preferred. It is contemplated that sealable coatings such as acrylic coatings and low temperature sealable coatings will adhere well to the primer of this invention.
- the coating weight of the primer of this invention is most easily controlled by the solids level. It is preferred to apply the primer at about 6% solids, which with our application method provides a primer coat weight of about 0.4 g/1000 square inches
- the coating weights of coatings applied to the primer of this invention are typical to those used in the film coating industry. Examples in this disclosure range between about 0.6% to about 1.3% solids which provides about 0.6 to about 1.3 g/msi, coating weight, depending upon the coating applied. However, this range should not be construe as limiting.
- Choline chloride can also be added to the primer formulation in amounts of about 0.25 parts per hundred poly(vinyl alcohol).
- the packaging material of the present invention includes (a) a packaging substrate that has a first surface layer and a second surface layer; (b) a precoating layer having a primer coated on at least one surface layers of the substrate, wherein the primer is a blend of poly (vinyl alcohol), an adhesion promoter and/or an epoxy resin; and (c) optionally a top coat layer and/or a metallic layer deposited thereon the precoating layer.
- the blend in the primer can further include a cross-linking agent and/or choline chloride.
- the packaging substrate of the present invention includes any polymeric film substrate which inherently permits the transmission of oxygen and water vapor, and wherein the utility of such film for packaging purposes would call for a minimization of such transmission.
- the polymeric materials include, but are not limited to, nylon, polyethylene teraphthaplate, polycarbonate, and polyolefins.
- the substrate is a polyolefin including, but not limited to polyethylene, polypropylene, polybutylene, terpolymers, copolymers, and blends thereof. More preferably, the substrate is an oriented polypropylene.
- Examples of the packaging substrate of the present invention can also include paperboards and fiberboard. Suitable examples of the paperboards and fiberboards can include, but are not limited to, glassine papers and clay coated papers.
- the packaging substrate of the present invention can be of any desired thickness. Generally, to ensure good machinability on high speed packaging equipment, the thickness of the substrate is from about 10 to about 50 microns, preferably, from about 10 to about 35 microns, and more preferably from about 12 to about 25 microns. At least one surface of the packaging substrate of the present invention is coated with a precoating layer by any coating method known in the art, e.g., gravure coating.
- the polymeric substrate can be pretreated to enhance the adhesion of the precoating layer to the polymeric substrate by any pretreatment known in the art.
- Pretreatments well known in the art include, but are not limited to, flame treatment, plasma treatment, chemical treatment and corona discharge treatment that are well known in the art.
- Flame treatment and corona discharge treatment are preferred with corona discharge treatment being particularly more preferred.
- the primer coating of the present invention is a blend of poly(vinyl alcohol), an adhesion promoter and/or an epoxy resin.
- the blend in the primer coating can further include a cross-linking agent and/or choline chloride.
- the thickness of the precoating layer is from about 0.5 to about 2.0 microns, preferably, from about 0.7 to about 1.5 microns, and more preferably from about 1.0 to about 1.5 microns.
- the weight ratio of the adhesion promoter and/or epoxy resin and polyvinyl alcohol is from about 0.15 to about 0.35, preferably from about 0.20 to about 0.30, and more preferably from about 0.22 to about 0.28.
- the weight ratio of the cross-linking agent and polyvinyl alcohol is from about 0.05 to about 0.4, preferably from about 0.10 to about 0.30, and more preferably from about 0.11 to about 0.12.
- the precoating layer of the present invention can optionally have a top coat layer and/or a metallic layer deposited thereon.
- the top coat layer can be applied on top of the precoating layer by any manner known in the art, e.g., gravure coating.
- the function of the top coat layer is to provide additional barriers and/or sealability and/or machinability and/or printability. Examples of coating materials to be used as a top coat layer are described in
- the coating materials include, but are not limited to, emulsions or solutions comprising poly(vinylidene) chloride, poly(vinyl chloride), poly(vinyl alcohol), ethylene acrylic acid copolymer, and acrylic.
- the thickness of the coating layer is up to 5.0 microns.
- the metal layer is deposited on the top layer by a manner known in the art, e.g., vacuum metallization or plasma deposition.
- the metal layer provides the packaging material with extra barrier and sealant properties.
- metals for the metal layer can include, but are not limited to, aluminum and aluminum oxide.
- EXAMPLE 1 PACKAGING FILMS OF THE PRESENT INVENTION This example illustrates the chemical barrier and adhesion properties of the packaging films of the present invention. Chemical barrier and adhesion tests were performed on eight film substrates having various coating compounds.
- Each of the eight film substrates was coated with eight different precoating layers of primer blends.
- the primer blends were applied utilizing a reverse direct gravure coating.
- the coated films were passed through a dry-air oven at about 125 ft/min. and at a temperature of 200 °F.
- the primer blends include PNOH, epoxy primer, and glyoxal.
- the primer blends are illustrated in Table 1.
- Each of the eight precoating layer was then coated with a top coating layer of an EAA formulation.
- the EAA formulation was applied utilizing a reverse direct gravure coater. The coated films were passed through a dry air oven at a temperature of 200 °F.
- the EAA formulation included lOOphr M4983 (Michernprime manufactured by Michelman), 1.5phr NaOH; 4phr carnaube wax emulsion (obtained from Michelman), 0.3phr silloid and 0.4phr talc.
- the resulting films were tested for oxygen transmission.
- the dried films were then tested in an oxygen-permeability device in which a stream of dry oxygen was passed through an aqueous salt solution-permeated pad to control the gas moisture content and then through the films, disposed at right angles to the stream with the top coating layer upstream.
- the oxygen transmitted was determined and the amount of oxygen passed per unit area of film per time period was calculated.
- the results of oxygen barrier tests are shown in Table 2.
- the packaging films of the present invention have low gas transmission and excellent adhesion property.
- the unique blend of the precoating layer of the present invention provides both chemical barrier and adhesion properties offer by the conventional packaging films.
- the blend of the precoating layer of the packaging films of the present invention eliminates the required primer layers of the conventional films.
- EXAMPLE 3 METALLIZED PACKAGING FILMS This example illustrates the chemical barrier and adhesion properties of conventional metallized packaging films and metallized packaging films of the present invention. Chemical barrier and adhesion tests were performed on nine MC550 film substrates (made by Mobil) having various coating compounds.
- the primer blends include PNOH, EAA, epoxy primer, and glyoxal.
- the primer blends are illustrated in Table 3.
- Each of the precoating layers was then metallized with a metal.
- the resulting films were tested for water vapor transmission, oxygen transmission, and adhesion properties. The results of the tests are illustrated in Table 4.
- Oriented polypropylene film samples (Samples 1-21) were primed with primer formulations described in the following table.
- M4983 is Michemprime manufactured by Michelman.
- M215 is a carnaube wax emulsion obtained from Michelman.
- SR344 is Tospearl 145 obtained by Toshiba Silicone Co.
- ML71513 is a synthetic wax obtained from Michelman.
- D8500 is Daran 8500 obtained from Hampshire Chemical.
- Each of the samples were tested for oxygen barrier properties and for sealability and the results of the testing are reported in Table 5 and Figures 1 to 5.
- ACNB 5ELVANOL 90/50 80 124 B 000 125 37 00 25 665 20 200 7 100 0 25 15 0 025 1403
- ACN8 6ELVANOL 90/50 80 B05 000 113 32 00 16 1034 20 200 5 loo 0 35 20 0 025 1553
- Figure 1 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties of the uncoated film.
- Figures 1 shows that high concentrations of poly(vinyl alcohol), which correspond to lower concentrations of epoxy, provide better oxygen barrier properties as does an increased coating weight.
- Figure 2 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties for the coated film.
- Figure 2 shows that, after top coating, all samples demonstrated better oxygen barrier properties than could be expected on the basis of the barrier contribution of the individual components.
- the low temperature sealable coating gave an oxygen barrier of 117 cm 3 / 100 rVday, which is approximately the barrier given by this gauge of polypropylene coated with polyethylene imine (129 cm 3 / 100 in 2 /day).
- the mean barrier for the samples that were coated with the low temperature sealable coating was about 3.7 cmVlOO in 2 /day.
- the barrier contribution of the low temperature sealable coating layer is about 1300 cmVlOO in 2 /day. Therefore, the expected oxygen transmission of the primed and coated film combination is expected to be no better than 3.69 cm 3 /100 in 2 /day.
- the expected value was calculated from the approximate barriers of the component layers:
- the value (1/3.7) includes the barrier of the oriented polypropylene and the primer.
- the value (1/300) was arrived at by subtracting the reciprocal of the barrier for polyethylene imine primed oriented polypropylene (1/117) from the reciprocal of the observed barrier of low temperature sealable coated polyethylene imine on the same gauge of oriented polypropylene (1/129).
- the actual mean value for the six samples was about 2.1 cm 3 / 100 in 2 /day . This value is lower than the mean value for any group of samples that only had the primer. It is about two-times as good as expected.
- the polyvinylidene chloride coated When a polyvinylidene chloride coated was applied to the primed film, at a relatively low coating weight the polyvinylidene chloride provided an oxygen barrier of about 0.85 cm 3 / 100 in 2 /day on epoxy-primed film which without the coating provided an oxygen barrier of 124 cm 3 / 100 in 2 /day. Therefore, the polyvinylidene chloride layer contributed 0.86 cm 3 / 100 in 2 /day to the barrier. If this coating is applied to a base sheet with a barrier of 2.6 cmVlOO in 2 /day, then the expected oxygen barrier should be about 0.81 cmVlOO in 2 /day. For the six polyvinylidene chloride coated samples, the mean value was 0.05 cmVlOO in 2 /day. This is sixteen times better than expected.
- Figure 3 is a plot showing the concentration of primer ingredients vs. oxygen barrier properties for the metallized film. Unlike the coated film samples, the metallized films show better barrier properties at low poly(vinyl alcohol) coating weights. When polyethylene imine or epoxy primed film was metallized the oxygen barrier values ranged from 1.5 to cm 3 / 100 in 2 /day. Switching to the poly(vinyl alcohol) primer, the mean oxygen transmission value was about 0.13 cmVlOO in 2 /day.
- FIG. 4 is a plot showing the concentration of primer ingredients vs. crimp- seal strength for coated films for seals formed at 127° C. the best results were achieved with a low temperature sealable coating but good effects were achieved with polyvinylidene chloride (Daran 8500) which performed better than acrylic. The improvement appears to relate to adhesion to primer. Higher epoxy levels in the primer improved the adhesion to the coatings.
- Figure 5 is another plot showing the concentration of primer ingredients vs. crimp-seal strength for coated films for seals formed at about 104°C. Similar results are achieved at lower temperatures. Surprisingly the low temperature sealable coating achieved improved seals at lower temperatures. At 82 °C the low temperature sealable coating still had seals of )400 g/in.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Wood Science & Technology (AREA)
- Life Sciences & Earth Sciences (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Laminated Bodies (AREA)
- Paints Or Removers (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Epoxy Resins (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP53498998A JP2001511211A (en) | 1997-02-10 | 1998-02-06 | Primer for plastic film |
AU61528/98A AU735361B2 (en) | 1997-02-10 | 1998-02-06 | Primer for plastic films |
BR9807569-1A BR9807569A (en) | 1997-02-10 | 1998-02-06 | Base for plastic films |
EP98906258A EP0960159A4 (en) | 1997-02-10 | 1998-02-06 | Primer for plastic films |
CA002280050A CA2280050A1 (en) | 1997-02-10 | 1998-02-06 | Primer for plastic films |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US3758597P | 1997-02-10 | 1997-02-10 | |
US60/037,585 | 1997-02-10 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO1998034982A1 true WO1998034982A1 (en) | 1998-08-13 |
Family
ID=21895138
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US1998/002498 WO1998034982A1 (en) | 1997-02-10 | 1998-02-06 | Primer for plastic films |
Country Status (10)
Country | Link |
---|---|
EP (1) | EP0960159A4 (en) |
JP (1) | JP2001511211A (en) |
KR (1) | KR20000070911A (en) |
CN (1) | CN1246879A (en) |
AR (1) | AR011658A1 (en) |
AU (1) | AU735361B2 (en) |
BR (1) | BR9807569A (en) |
CA (1) | CA2280050A1 (en) |
ID (1) | ID23409A (en) |
WO (1) | WO1998034982A1 (en) |
Cited By (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7517820B2 (en) | 2002-01-17 | 2009-04-14 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Polymers for water-permeable protective materials |
US8829111B2 (en) * | 2004-09-30 | 2014-09-09 | The Queen's University Of Belfast | Polymer material |
US9303179B2 (en) | 2012-11-02 | 2016-04-05 | Michelman, Inc. | Primer coating for metallized gas barrier films |
US20220126416A1 (en) * | 2019-07-10 | 2022-04-28 | AGC Inc. | Glass substrate and method for manufacturing same |
CN114854155A (en) * | 2022-04-06 | 2022-08-05 | 杭州师范大学 | High-strength, anti-freezing and transparent conductive PVA/quaternary ammonium salt elastomer |
US20220388745A1 (en) * | 2021-06-01 | 2022-12-08 | Mondi Ag | Film composite, film packaging, and method for the production of a film composite |
Families Citing this family (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2012005288A1 (en) | 2010-07-09 | 2012-01-12 | 日本合成化学工業株式会社 | Saponified ethylene/vinyl ester copolymer composition and multilayer structure using the composition |
CN104962146A (en) * | 2015-07-03 | 2015-10-07 | 海南必凯水性涂料有限公司 | High-oxygen-barrier self-adhesive polyvinyl alcohol coating and preparation method thereof |
CN104961903A (en) * | 2015-07-03 | 2015-10-07 | 海南赛诺实业有限公司 | High-oxygen-barrier no-primer polyvinyl alcohol coated film and manufacturing method thereof |
JP2019530565A (en) * | 2016-09-14 | 2019-10-24 | ビーエーエスエフ ソシエタス・ヨーロピアBasf Se | Method for producing polymer film having gas barrier property |
CN109747971A (en) * | 2017-11-08 | 2019-05-14 | 林紫绮 | The method that cation water-based solution manufacture prevents ink pollution packaging material |
US11884466B2 (en) | 2020-12-11 | 2024-01-30 | Sonoco Development, Inc. | Sustainable barrer containers and methods |
EP4200132A1 (en) * | 2020-12-11 | 2023-06-28 | Sonoco Development, Inc. | Sustainable barrer containers and methods |
GB2628562A (en) | 2023-03-28 | 2024-10-02 | Innovia Films Ltd | Barrier film |
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US4214039A (en) * | 1979-04-23 | 1980-07-22 | Mobil Oil Corporation | Polypropylene film with primer of a water dispersed epoxy resin coating |
US5487940A (en) * | 1991-12-23 | 1996-01-30 | Mobil Oil Corp. | Oxygen and moisture barrier metallized film structure |
US5496649A (en) * | 1994-07-21 | 1996-03-05 | Mobil Oil Corp. | Cross-linked PVOH coatings having enhanced barrier characteristics |
US5547764A (en) * | 1994-12-22 | 1996-08-20 | Mobil Oil Corporation | Method of producing PVOH coatings with enhanced properties |
US5552212A (en) * | 1990-12-13 | 1996-09-03 | Mobil Oil Corporation | High barrier film combination |
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US5192620A (en) * | 1991-11-08 | 1993-03-09 | Mobil Oil Corporation | Metallized composite film structure and method |
JPH06228347A (en) * | 1993-01-29 | 1994-08-16 | Teijin Ltd | Easily bondable antistatic polyester film |
EP0794861A4 (en) * | 1994-12-02 | 1998-08-12 | Mobil Oil Corp | Heat sealable multilayer film containing polyvinyl alcohol layer |
-
1998
- 1998-02-06 KR KR1019997007176A patent/KR20000070911A/en not_active Application Discontinuation
- 1998-02-06 EP EP98906258A patent/EP0960159A4/en not_active Withdrawn
- 1998-02-06 ID IDW990853D patent/ID23409A/en unknown
- 1998-02-06 CA CA002280050A patent/CA2280050A1/en not_active Abandoned
- 1998-02-06 BR BR9807569-1A patent/BR9807569A/en not_active Application Discontinuation
- 1998-02-06 CN CN98802385A patent/CN1246879A/en active Pending
- 1998-02-06 WO PCT/US1998/002498 patent/WO1998034982A1/en not_active Application Discontinuation
- 1998-02-06 JP JP53498998A patent/JP2001511211A/en active Pending
- 1998-02-06 AU AU61528/98A patent/AU735361B2/en not_active Ceased
- 1998-02-10 AR ARP980100590A patent/AR011658A1/en unknown
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US4214039A (en) * | 1979-04-23 | 1980-07-22 | Mobil Oil Corporation | Polypropylene film with primer of a water dispersed epoxy resin coating |
US5552212A (en) * | 1990-12-13 | 1996-09-03 | Mobil Oil Corporation | High barrier film combination |
US5487940A (en) * | 1991-12-23 | 1996-01-30 | Mobil Oil Corp. | Oxygen and moisture barrier metallized film structure |
US5496649A (en) * | 1994-07-21 | 1996-03-05 | Mobil Oil Corp. | Cross-linked PVOH coatings having enhanced barrier characteristics |
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DATABASE ORBIT WPAT 1 January 1900 (1900-01-01), XP002911017, Database accession no. 94-238896/29 * |
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DATABASE STN CAPLUS 1 January 1900 (1900-01-01), XP002911016, Database accession no. 126:239203 * |
See also references of EP0960159A4 * |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US7517820B2 (en) | 2002-01-17 | 2009-04-14 | The Secretary Of State For Defence In Her Britannic Majesty's Government Of The United Kingdom Of Great Britain And Northern Ireland | Polymers for water-permeable protective materials |
US8829111B2 (en) * | 2004-09-30 | 2014-09-09 | The Queen's University Of Belfast | Polymer material |
US9303179B2 (en) | 2012-11-02 | 2016-04-05 | Michelman, Inc. | Primer coating for metallized gas barrier films |
US10005918B2 (en) | 2012-11-02 | 2018-06-26 | Michelman, Inc. | Primer coating for metallized gas barrier films |
US20220126416A1 (en) * | 2019-07-10 | 2022-04-28 | AGC Inc. | Glass substrate and method for manufacturing same |
US20220388745A1 (en) * | 2021-06-01 | 2022-12-08 | Mondi Ag | Film composite, film packaging, and method for the production of a film composite |
CN114854155A (en) * | 2022-04-06 | 2022-08-05 | 杭州师范大学 | High-strength, anti-freezing and transparent conductive PVA/quaternary ammonium salt elastomer |
CN114854155B (en) * | 2022-04-06 | 2023-08-22 | 杭州师范大学 | High-strength, freeze-resistant and transparent conductive PVA/quaternary ammonium salt elastomer |
Also Published As
Publication number | Publication date |
---|---|
CN1246879A (en) | 2000-03-08 |
EP0960159A1 (en) | 1999-12-01 |
AU6152898A (en) | 1998-08-26 |
AR011658A1 (en) | 2000-08-30 |
CA2280050A1 (en) | 1998-08-13 |
ID23409A (en) | 2000-04-20 |
JP2001511211A (en) | 2001-08-07 |
KR20000070911A (en) | 2000-11-25 |
BR9807569A (en) | 2000-02-01 |
EP0960159A4 (en) | 2001-04-04 |
AU735361B2 (en) | 2001-07-05 |
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