Coating composition for forming gas barrier layer, gas barrier film, and method for producing gas barrier film

Patent metadata

Field	Value
Publication number	US-9540537-B2
Application number	US-201214000053-A
Country	US
Kind code	B2
Filing date	Feb 22, 2012
Priority date	Feb 24, 2011
Publication date	Jan 10, 2017
Grant date	Jan 10, 2017

Abstract

Provided are a coating composition for forming a gas barrier layer as configured such that a specific compound having two or more 5-membered cyclic carbonate groups and a compound having two or more amino groups are reactable at an equivalent ratio of functional groups of 0.8 to 1.25 to form the gas barrier layer with a polyhydroxyurethane resin as a principal component; a gas barrier film formed of a single layer or multiple layers, at least one of the layer or layers that forms or form the film is a layer that exhibits gas barrier properties, and the layer is formed of a polyhydroxyurethane resin having a specific chemical structure; and a production method of a film having gas barrier properties. Owing to the use of the specific polyhydroxyurethane resin, the coating composition, gas barrier film and production method readily enable to reduce moisture-dependent variations in gas barrier properties, to avoid the production of noxious fumes upon incineration disposal, to provide excellent processability, and to lower the pollutant load on the environment.

First claim

The invention claimed is:

1. A coating composition for forming a gas barrier layer that exhibits gas barrier properties, the coating composition comprising:
a carbonate compound having at least three 5-membered cyclic carbonate groups as Component A; and
an amine compound having at least two amino groups as Component B,
wherein the carbonate compound and the amine compound in the composition react at an equivalent ratio of functional groups from 0.8 to 1.25 so as to form polyhydroxyurethane resin as a principal component in the gas barrier layer, and
the equivalent ratio of functional groups is obtained by a following formula:
Equivalent ratio=(mass of the carbonate compound in the coating composition×a number of functional groups in the carbonate compound/molecular weight of the carbonate compound)/(mass of the amine compound in the coating composition×a number of functional groups in the amine compound/molecular weight of the amine compound),

where the number of functional groups in the carbonate compound means a number of cyclic carbonate structures in a molecule of the carbonate compound, and
the number of functional groups in the amine compound means a number of amino groups in a molecule of the amine compound, and
wherein the carbonate compound is at least one compound selected from the group consisting of

2. The coating composition according to claim 1 ,
wherein carbon dioxide has been used as a raw material for —CO—O— bonds in the 5-membered cyclic carbonate groups, and
the gas barrier layer comprises the —CO—O— bonds derived from the carbon dioxide in an amount from 1 to 30 mass % relative to the gas barrier layer formed from the coating composition.

3. The coating composition according to claim 1 , wherein the amine compound having the amino groups as the Component B comprises meta-xylylenediamine, 1,3-bis(aminomethyl)cyclohexane, or a combination thereof.

4. A gas barrier film, comprising a gas barrier layer formed from the coating composition according to claim 1 ,
wherein the gas barrier film is a single gas barrier film or a multilayer gas barrier film,
the gas barrier layer has a thickness in a range from 0.1 to 200 μm, and
the gas barrier layer has an oxygen permeation rate of no higher than 50 mL/m 2 ·24 h·atm at a temperature of 23° C. and humidity in a range from 0% to 90% when measured according to JIS K-7126.

5. A production method of a gas barrier film formed of a single layer or multiple layers, at least one of said layer or layers that forms or form the gas barrier film being a gas barrier layer that exhibits gas barrier properties, which comprises:
applying, to a surface of a base material or a surface of a release paper, a coating composition,
wherein the coating composition comprises:
a carbonate compound having at least three 5-membered cyclic carbonate groups as Component A; and
an amine compound having at least two amino groups as Component B,

wherein the carbonate compound and the amine compound react at an equivalent ratio of functional groups, as defined by a following equation, from 0.8 to 1.25 so as to form the polyhydroxyurethane resin, and
the equivalent ratio of functional groups is obtained by a following formula:
Equivalent ratio=(mass of the carbonate compound in the coating composition×number of functional groups in the carbonate compound/molecular weight of the carbonate compound)/(mass of the amine compound in the coating composition×number of functional groups in the amine compound/molecular weight of the amine compound),

where the number of functional groups in the carbonate compound means a number of cyclic carbonate structures in a molecule of the carbonate compound, and
the number of functional groups in the amine compound means a number of amino groups in a molecule of the amine compound, and
wherein the carbonate compound is at least one compound selected from the group consisting of

6. The production method according to claim 5 , wherein the amine compound having the amino groups as the Component B comprises meta-xylylenediamine, 1,3-bis(aminomethyl)cyclohexane, or a combination thereof.

7. A method for protecting a material from gas present in an environment, comprising:
covering the material with a gas barrier film so as to prevent the gas from permeating through the gas barrier film,
wherein the gas barrier film is formed of a single layer or multiple layers,
the single layer or at least one of said multiple layers exhibits gas barrier properties,
the layer that exhibits the gas barrier properties comprises a film that comprises a polymer having, as a repeating unit in a main chain of the polymer, at least one chemical structure selected from the group consisting of structures represented by following formulas from (2-1) to (2-4), and
the polymer is polyhydroxyurethane resin comprising, as monomer units, a carbonate compound having two 5-membered cyclic carbonate groups and an amine compound having at least two amino groups, and
the polymer is obtained by an addition reaction of the monomer units,

wherein Xs and Ys represent chemical structures formed of hydrocarbons or aromatic hydrocarbons derived from the monomer units, and
the structures may each contain at least one hetero atom selected from the group consisting of oxygen, nitrogen, and sulfur,
wherein the carbonate compound is at least one compound selected from the group consisting of

where R is hydrogen or CH 3 ,
the amine compound is selected from the group consisting of linear aliphatic polyamines, cyclic aliphatic polyamines, aliphatic polyamines having aromatic rings, and aromatic polyamines,
the layer that exhibits the gas barrier properties has a thickness in a range from 0.1 to 100 μm, and
the polymer film has an oxygen permeation rate of no higher than 50 mL/m 2 ·24 h·atm at a temperature of 23° C. and humidity in a range from 0% to 90% when measured according to JIS K-7126.

8. The method according to claim 7 ,
wherein the material is at least one material selected from the group consisting of foods, pharmaceuticals, cosmetics, and daily necessaries.

9. The method according to claim 7 , wherein the polyhydroxyurethane resin has a weight average molecular weight in a range from 10,000 to 100,000 and a hydroxyl number in a range from 180 to 350 mgKOH/g.

10. The method according to claim 7 ,
wherein the carbonate compound has been synthesized using carbon dioxide as a raw material, and
—O—CO— bonds derived from the carbon dioxide account for from 1 to 30 mass % relative to the polyhydroxyurethane resin, which is obtained using the carbonate compound as the monomer unit.

11. The method according to claim 7 ,
wherein the single layer or at least one of the multiple layers that exhibits the gas barrier properties is formed by a process comprising:
applying a solution of an organic solvent comprising the polyhydroxyurethane resin, which is defined in claim 7 , to a base material, and
evaporating a volatile componen

Assignees

• Takahashi Kenichi
• Uruno Manabu
• Kimura Kazuya
• Hanada Kazuyuki
• Dainichiseika Color Chem
• Ukima Colour & Chem Mfg

Inventors

• Takahashi Kenichi
• Uruno Manabu
• Kimura Kazuya
• Hanada Kazuyuki

Classifications

• C08J7/0427

  with only one layer of a composition containing a polymer binder (with more layers C08J7/042) · CPC title

• Y10T428/269

  including synthetic resin or polymer layer or component · CPC title

• C08G71/04

  Polyurethanes · CPC title

• Y10T428/1352

  Polymer or resin containing [i.e., natural or synthetic] · CPC title

• Y10T428/1321

  Polymer or resin containing [i.e., natural or synthetic] · CPC title