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GB2427575A - Polyolefin coated with a partially crosslinked polyvinyl alcohol vinyl amine intermediate layer - Google Patents

Polyolefin coated with a partially crosslinked polyvinyl alcohol vinyl amine intermediate layer Download PDF

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Publication number
GB2427575A
GB2427575A GB0512776A GB0512776A GB2427575A GB 2427575 A GB2427575 A GB 2427575A GB 0512776 A GB0512776 A GB 0512776A GB 0512776 A GB0512776 A GB 0512776A GB 2427575 A GB2427575 A GB 2427575A
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GB
United Kingdom
Prior art keywords
coating
polyvinyl alcohol
vinyl amine
copolymer
film
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.)
Withdrawn
Application number
GB0512776A
Other versions
GB0512776D0 (en
Inventor
Rohan Ratnakumar
Jonathan Hewitt
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.)
Innovia Films Ltd
Original Assignee
Innovia Films 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 Innovia Films Ltd filed Critical Innovia Films Ltd
Priority to GB0512776A priority Critical patent/GB2427575A/en
Publication of GB0512776D0 publication Critical patent/GB0512776D0/en
Publication of GB2427575A publication Critical patent/GB2427575A/en
Withdrawn legal-status Critical Current

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Classifications

    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/65—Additives macromolecular
    • 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
    • C09D139/00—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 a single or double bond to nitrogen or by a heterocyclic ring containing nitrogen; Coating compositions based on derivatives of such polymers
    • C09D139/02—Homopolymers or copolymers of vinylamine
    • 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
    • B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
    • B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
    • 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
    • B32B27/18—Layered products comprising a layer of synthetic resin characterised by the use of special additives
    • B32B27/26—Layered products comprising a layer of synthetic resin characterised by the use of special additives using curing agents
    • 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
    • B32B27/28—Layered products comprising a layer of synthetic resin comprising synthetic resins not wholly covered by any one of the sub-groups B32B27/30 - B32B27/42
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
    • C08J7/04—Coating
    • C08J7/0427—Coating with only one layer of a composition containing a polymer binder
    • 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
    • C09D7/125—
    • 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
    • B32B2323/00—Polyalkenes
    • B32B2323/10—Polypropylene
    • 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
    • B32B2329/00—Polyvinylalcohols, polyvinylethers, polyvinylaldehydes, polyvinylketones or polyvinylketals
    • 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
    • B32B2333/00—Polymers of unsaturated acids or derivatives thereof
    • 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
    • B32B2386/00—Specific polymers obtained by polycondensation or polyaddition not provided for in a single one of index codes B32B2363/00 - B32B2383/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2323/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
    • C08J2323/02—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers not modified by chemical after treatment
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2429/00—Characterised by the use of 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; Hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Derivatives of such polymer
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L29/00—Compositions of 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; Compositions of hydrolysed polymers of esters of unsaturated alcohols with saturated carboxylic acids; Compositions of derivatives of such polymers
    • C08L29/02—Homopolymers or copolymers of unsaturated alcohols
    • C08L29/04—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
    • C08L33/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
    • C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L61/00—Compositions of condensation polymers of aldehydes or ketones; Compositions of derivatives of such polymers
    • C08L61/20—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
    • C08L61/26—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds
    • C08L61/28—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes with heterocyclic compounds with melamine

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Laminated Bodies (AREA)

Abstract

The film is produced by coating at least one side of a polyolefinic substrate with a solution of a polyvinyl alcohol-vinyl amine and an aldehyde-containing crosslinking agent for crosslinking said copolymer and then drying the coating. The polyvinyl alcohol-vinyl amine copolymer is less than fully cross linked throughout so as to enable a top coat to adhere to the polymeric film structure. The disclosed film includes a polypropylene substrate which has been treated by corona discharge, a melamine formaldehyde crosslinking agent and a clear ethylene acrylic acid emulsion top coat. The film is used in food packaging.

Description

DESCRIPTION
POLYMERIC FILM STRUCTURES
This invention relates to polymeric film structure more particularly to a polymeric olefinic film structure produced by a process comprising coating at least one side of a polyolefinic substrate with a solution of a polyvinyl alcohol-vinyl amine and an crosslinking agent for crosslinking said copolymer and then drying the coating, the quantity by weight of the cross linking agent present in the coating solution being regulated so that the polyvinyl alcohol-vinyl amine copolymer present in the coating solution is not fully cross linked thus enabling a top coat to adhere to the polymeric film structure.
US 6,559,227 discloses a process for producing a powdered water-soluble powdered vinylamine-vinyl alcohol copolymer comprising hydrolyzing a copolymer comprising an N-vinylamide unit and a vinyl acetate unit while dispersed in water under a basic condition and then washing the resulting powdered water-soluble polymer with at least one washing liquid selected from an alcohol, water at 20.degree. C. or lower, and salt water.
US 6,559,227 states that the water-soluble polymer produced by the abovedescribed process can be used as, for example, wet-end paper additives, dry-end paper additives, a dispersant, coatings applied to paper or a plastic film, and hair care products such as a shampoo. The polymer exhibits the respective desired functions in these uses. When used as a coating of a plastic film, etc., the polymer has a sufficiently low content of impurities and undergoes no reduction of transparency or color change.
US published application 20050043472 discloses an amine-functional copolymer improved in color and odor, and a method for efficiently producing the amine-functional copolymer in the form of a powder by efficiently hydrolyzing a vinyl alcohol/N-vinyl carboxamide, are provided. The amine-functional copolymer, of which a 10 wt % aqueous solution has a Gardner index of at most 3 as measured in accordance with ASTM Dl 544. Such a copolymer is obtainable by a method for producing an amine functional copolymer by hydrolyzing N-vinyl carboxamide copolymer in the presence of an acid or base catalyst, wherein the hydrolysis is carried out in an aqueous medium having a salt dissolved therein.
US published application 20050043472 states that the polymer of the invention may preferably be employed also for a gas barrier material.
US 5,776,618 discloses a polymeric film structure exhibiting improved barrier properties and which is formed in the absence of a primer. The film structure is produced by coating a surface of a polymeric substrate with a solution of a polyvinyl alcohol-vinyl amine copolymer, an aldehydecontaining crosslinking agent and a crosslinking promoting acid catalyst. The polymer substrate is made out of polyolefin materials such as polypropylene.
The coating of US5776618 contains an aldehyde-containing crosslinking agent in an amount sufficient to effect crosslinking throughout the polyvinyl alcohol-vinyl amine copolymer that is added to the coating solution. To promote and facilitate the crosslinking of the polyvinyl alcohol-vinyl amine copolymer, a catalytically-effective amount of a crosslinkingpromoting acid catalyst is added to the coating solution. The acid catalyst is preferably selected from the following acids: hydrochloric acid (HCL), sulfuric acid (H.sub.2 SO.sub.4), phosphoric acid (H.sub.3 PO.sub.4) and acetic acid (CH.sub.3 COOH). The pH of the coating solution is preferably maintained within the range of from about I to about 6, and more preferably at a pH of about 2 to about 4.
We have now found that by limiting the amount of crosslinking agent and avoiding the presence of an cross-linking promoting acid catalyst in a polyvinyl alcohol-vinyl amine copolymer coating solution, it is possible to coat a polymeric oleuinic film surface so that the coating produced not only has adequate gas barrier properties but also acts as receptive surface for further top coating to produce a final product with e.g good heat sealing properties and/or printability.
According to the invention there is provided a polymeric olefinic film structure produced by a process comprising coating at least one side of a polyolefinic substrate with a solution of a polyvinyl alcohol-vinyl amine and an aldehyde-containing crosslinking agent for crosslinking said copolymer and then drying the coating, the quantity by weight of the cross linking agent present in the coating solution being regulated so that the polyvinyl alcohol-vinyl amine copolymer present in the coating solution is less than fully cross linked throughout so as to enable a top coat to adhere to the polymeric film structure.
We prefer to use a polyvinyl alcohol-vinyl amine which contains about 13% by weight of polyvinylam me We prefer to coat a polypropylene film surface which has been treated in a conventional manner with a corona discharge.
Suitable cross linking agents include those based on formaldehyde such as melamine formaldehyde. We have found that under normal drying conditions such as with an oven temperature of 95deg C for 45 seconds using about l. % solids of a melamine formaldehyde of the coating solution as crosslinker enables a coating to be obtained to which a top coat adheres satisfactorily and therefore good heat sealing performance is obtained. We have found that as the amount of cross linker measured as dry solids is increased to above about 2 % there is a dramatic fall in heat sealing performance.
Typical top coating heat sealable compositions such as those based on the use of acrylic emulsions can be satisfactorily applied to the partially cross linked polyvinyl alcohol- vinyl amine coating.
Our invention also includes a heat sealable polymeric olefinic film with an acrylic based heat sealed coat adhering to a polyvinyl alcohol-vinyl amine copolymer coating, and food packages made therefrom.
Packages for fresh foodstuffs need to retain their heat seal strength under humid conditions and samples formed from the films of the present invention retained a satisfactory heat seal strength when held at 90% RH and 38 deg C for four weeks.
Figure one plots the results given in the table set out in Example 2 and demonstrates the change in adhesion of the top coating as the amount of cross linker present is increased.
These results are those obtained with the particular cross linker used, the amount of cross linker which must not be exceeded to obtain adequate adherence of a top coat will of course vary with the activity of any specific cross linker but as can be seen this can be easily determined in the same manner as has been done in Example 2 for a particular grade of melamine formaldehyde.
The following examples illustrate but do not limit the invention
Example I
20g of a polyvinyl alcohol vinylamine copolymer in powder form available as Diafix from Mitsibushj Chemical Corporation via their distributors Esprix Technologies of 7680 Matoaka Road Sarasota, FL 34243 USA was added to a stirred beaker with lOOg of water. The water temperature was maintained at 27-29 deg C. The mixture was stirred until a smooth slurry was obtained and then heated using a magnetic stirrer heater to 90 deg C. The solution thus formed was then cooled to room temperature and a cloudy suspension was decanted off for use as a coating. This suspension had a solids content of about 2.083%. measured by drying in an oven.
0.5 ml of melamine formaldehyde suspension available from BIP Chemicals under the designation PT807 containing 8.4% melamine formaldehyde was added to 50 ml of the polyvinyl alcohol vinylamine copolymer suspension giving a cross linker content of 2 per cent as dry solids and drawn down onto a corona discharge treated surface of a 28u polypropylene film. The coating was dried with a heated air dryer and a clear glossy coating was obtained.
An ethylene acrylic acid dispersion sold under the trade name Aquaseal 1290 by Paramemt BV of Costerstraat 18 1704 Ri Heerhugowaard Postbus 86 1700 AB Heerhugowaard Netherlands.was drawn down on top of the polyvinyl alcohol vinylamine copolymer coating obtained as above. The resultant coating was dried at 100 deg C for about 40 seconds and a clear adherent film was obtained.
A satisfactory heat seal strength of over just over 700 g/25mm was obtained when the coated film was sealed using a Sentinel type heat sealer with sealing jaws set at l3Odeg C at 15 psi for for 2 seconds dwell time.
Coating was carried out using a RK draw down bench with a red K-bar which applies 2 gms of wet coating per sq m.
Example 2.
A series of coated films were produced as described in Example one except that the quantity of cross linker used was varied to demonstrate the deterioration in heat seal properties with increasing quantities of cross linker. Table one shows the results obtained and it can be seen that samples 5 to 11 show the major change in heat sealing effectiveness when the content of cross linker is increased to 1.9 % as dry solids weight of the total dry solids content of the polyvinyl alcohol vinylamine copolymer coating dispersion. Another factor affected by the content of cross linker is the appearance of the dried coating. Thus although Sample one with no cross linker gave adequate heat seal properties, its appearance was unsatisfactory indicating that a cross linker must be present to give a marketable product.
ME = melamine formaldehyde crosslinker P1708 from BIP I Sample MF I Dry % Ave seals I Tape gI25mm adhesion - 1 00 595 good - 2 08 448 good 3 11 335 good 4 17 583 good - 5 1.9 161 good - 6 4.0 - 159 good 7 -- 61 107 good 8 - 92 107 good L 9 139 117 good L 10 21 7 0 partial pull off [ 11 395 0 total pull off

Claims (1)

  1. A polymeric olefinic film structure produced by a process comprising coating at least one side ofa polyolefinic substrate with a solution ofa polyvinyl alcohol- vinyl amine and an aldehyde-containing crosslinking agent for crosslinking said copolymer and then drying the coating, the quantity by weight of the cross linking agent present in the coating solution being regulated so that the polyvinyl alcohol-vinyl amine copolymer present in the coating solution is less than fully cross linked throughout so as to enable a top coat to adhere to the polymeric film structure.
GB0512776A 2005-06-23 2005-06-23 Polyolefin coated with a partially crosslinked polyvinyl alcohol vinyl amine intermediate layer Withdrawn GB2427575A (en)

Priority Applications (1)

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GB0512776A GB2427575A (en) 2005-06-23 2005-06-23 Polyolefin coated with a partially crosslinked polyvinyl alcohol vinyl amine intermediate layer

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Application Number Priority Date Filing Date Title
GB0512776A GB2427575A (en) 2005-06-23 2005-06-23 Polyolefin coated with a partially crosslinked polyvinyl alcohol vinyl amine intermediate layer

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GB0512776D0 GB0512776D0 (en) 2005-07-27
GB2427575A true GB2427575A (en) 2007-01-03

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010040707A1 (en) 2008-10-07 2010-04-15 Basf Se Printable gas barriers
WO2010093366A1 (en) * 2009-02-13 2010-08-19 Exxonmobil Oil Corporation Barrier film structures
JP7147105B1 (en) * 2021-03-30 2022-10-04 積水化学工業株式会社 Coating agents, paint films, and laminated packaging materials

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116376081A (en) * 2021-12-23 2023-07-04 江阴纳力新材料科技有限公司 Modified polymer film, preparation method thereof, metallized polymer film and application

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776618A (en) * 1996-07-25 1998-07-07 Mobil Oil Corporation Barrier film structures

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5776618A (en) * 1996-07-25 1998-07-07 Mobil Oil Corporation Barrier film structures

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010040707A1 (en) 2008-10-07 2010-04-15 Basf Se Printable gas barriers
WO2010093366A1 (en) * 2009-02-13 2010-08-19 Exxonmobil Oil Corporation Barrier film structures
JP7147105B1 (en) * 2021-03-30 2022-10-04 積水化学工業株式会社 Coating agents, paint films, and laminated packaging materials
WO2022210208A1 (en) * 2021-03-30 2022-10-06 積水化学工業株式会社 Coating agent, coating film, and laminated packaging material

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Publication number Publication date
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