# US 9,428,316 B2 · Resin for oxygen-absorbing adhesive and oxygen-absorbing adhesive

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- Number: US 9,428,316 B2
- Document ID: US9428316B2
- Status: Granted
- Kind: B2
- Application number: 14/594,579
- Filed: 2015-01-12
- Published: 2015-05-07
- Granted: 2016-08-30
- Earliest claimed: 2010-08-19
- Assignees: Toyo Seikan Group Holdings, Ltd.
- Applicants: Toyo Seikan Group Holdings, Ltd.
- Inventors: Yoshihiro Ohta; Yoichi Ishizaki; Yui Asano
- Web page: https://patentgrep.com/patent/US9428316B2

## CPC

- B65D 81/266: {for absorbing gases, e.g. oxygen absorbers or desiccants (B65D51/244, B65D51/30 take precedence)}
- B01J 20/264: {derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 15/09: comprising polyesters
- C08G 63/183: Terephthalic acids
- C08G 63/54: the acids or hydroxy compounds containing carbocyclic rings
- C09J 167/02: Polyesters derived from dicarboxylic acids and dihydroxy compounds (C09J167/06 takes precedence)
- C09J 167/06: Unsaturated polyesters having carbon-to-carbon unsaturation
- B32B 2255/06: on metal layer
- B32B 2255/26: Polymeric coating
- B32B 2307/74: Oxygen absorber
- Y10T 428/31794: Of cross-linked polyester
- 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
- B01J: CHEMICAL OR PHYSICAL PROCESSES, e.g. CATALYSIS OR COLLOID CHEMISTRY; THEIR RELEVANT APPARATUS
- B32B: LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- C08G: MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C09J: ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES (preparation of glue or gelatine C09H)
- Y10T: TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION

## Abstract

A two-component curable oxygen-absorbing composition comprises a polyester comprising structural units derived from an acid component (A) and an acid component (B), wherein the ratio of the acid component (A) to total acid components is 70 mol % to 95 mol %, the ratio of the acid component (B) to total acid components is 0 mol % to 15 mol %, the polyester has a glass transition temperature of −20° C. to 0° C., the resin is cured using a diisocyanate hardening agent, and the acid component (A) is a tetrahydrophthalic acid or a derivative thereof, or a tetrahydrophthalic acid anhydride or a derivative thereof, and the acid component (B) is a phthalic acid or an analog thereof.

## Claims

### Claim 1

A two-part curable oxygen-absorbing resin composition comprising:
(i) a main agent comprising a resin, wherein
the resin is a polyester comprising structural units derived from an acid component (A) and an acid component (B),
the ratio of the acid component (A) is 70% to 95% by mole relative to all acid components,
the ratio of the acid component (B) is 0% to 15% by mole relative to the all acid components, and
the glass transition temperature of the polyester is −20° C. to 0° C.; and
(ii) a curing agent component selected from the group consisting of aliphatic diisocyanates, alicyclic diisocyanates, and combinations thereof,
wherein:
the acid component (A) is a tetrahydrophthalic acid, a derivative thereof, a tetrahydrophthalic anhydride, or a derivative thereof, wherein the derivative is an ester, an acid halide, a substituted compound, or an oligomer and
the acid component (B) is a phthalic acid or an analog of the phthalic acid.

### Claim 2 (depends on 1)

The two-part curable oxygen-absorbing resin composition according to claim 1, wherein the acid component (A) is a methyltetrahydrophthalic acid, a derivative thereof, a methyltetrahydrophthalic anhydride, or a derivative thereof.

### Claim 3 (depends on 1)

The two-part curable oxygen-absorbing resin composition according to claim 1, wherein
the acid component (A) contains 50% by mole or more of an acid component having a structure selected from the group consisting of (i) and (ii):
(i) a tetrahydrophthalic acid, a derivative thereof, a tetrahydrophthalic anhydride, or a derivative thereof having a carbon atom which is bonded to both groups having the following structures (a) and (b) and also which is bonded to one or two hydrogen atoms, the carbon atom being included in an alicyclic structure:
(a) a carbon-carbon double bond group,
(b) an oxygen atom-containing functional group or a linking group derived from the functional group; and
(ii) a tetrahydrophthalic acid, a derivative thereof, a tetrahydrophthalic anhydride, or a derivative thereof in which
a carbon atom adjacent to a carbon-carbon double bond in an unsaturated alicyclic structure is bonded to an electron-donating substituent and a hydrogen atom,
another carbon atom adjacent to the carbon atom is bonded to a hetero atom-containing functional group or a linking group derived from the functional group, and
the electron-donating substituent and the hetero atom-containing functional group or the linking group derived from the functional group are in a cis configuration.

### Claim 4 (depends on 3)

The two-part curable oxygen-absorbing resin composition according to claim 3, wherein
the acid component having the structure of (i) is 4-methyl-Δ3-tetrahydrophthalic acid, a derivative thereof, 4-methyl-Δ3-tetrahydrophthalic anhydride, or a derivative thereof, and
the acid component having the structure of (ii) is cis-3-methyl-Δ4-tetrahydrophthalic acid, a derivative thereof, cis-3-methyl-Δ4-tetrahydrophthalic anhydride, or a derivative thereof.

### Claim 5 (depends on 1)

The two-part curable oxygen-absorbing resin composition according to claim 1, wherein the resin is the polyester further comprising a structural unit derived from 1,4-butanediol.

### Claim 6 (depends on 1)

The two-part curable oxygen-absorbing resin composition according to claim 1, comprising a structural unit derived from an aliphatic dicarboxylic acid, which is a further acid component, in an amount of 1% to 30% by mole relative to the all acid components.

### Claim 7 (depends on 6)

The two-part curable oxygen-absorbing resin composition according to claim 6, wherein the aliphatic dicarboxylic acid is succinic acid or adipic acid.

### Claim 8 (depends on 1)

An oxygen-absorbing adhesive comprising the two-part curable oxygen-absorbing resin composition according to claim 1.

### Claim 9 (depends on 1)

An oxygen-absorbing laminated film comprising at least:
an oxygen barrier film layer;
an oxygen-absorbing layer made of the oxygen-absorbing adhesive according to claim 1; and
a sealant film layer.