# US 12,006,451 B2 · Two-component solvent-less adhesive composition

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- Number: US 12,006,451 B2
- Document ID: US12006451B2
- Status: Granted
- Kind: B2
- Application number: 17/414,584
- Filed: 2018-12-21
- Published: 2022-02-24
- Granted: 2024-06-11
- Earliest claimed: 2018-12-21
- Assignees: Dow Global Technologies LLC; Rohm and Haas Company
- Applicants: Dow Global Technologies LLC; Rohm and Haas Company
- Inventors: Rui Shi; Zhaohui Qu; Yinzhong Guo
- Web page: https://patentgrep.com/patent/US12006451B2

## CPC

- C09J 175/06: from polyesters
- B32B 5/022: {Non-woven fabric}
- B32B 5/26: another layer {next to it} also being fibrous or filamentary {(relative arrangement of fibres or filaments of different layers B32B5/12)}
- B32B 7/12: using interposed adhesives or interposed materials with bonding properties
- B32B 9/02: comprising animal or vegetable substances {, e.g. cork, bamboo, starch}
- B32B 9/04: comprising such {particular} substance as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a glass layer B32B17/06; layered products with at least two ceramic layers composed mainly of ceramic B32B18/00)}
- B32B 9/041: {of metal}
- B32B 9/045: {of synthetic resin}
- B32B 9/047: {made of fibres or filaments}
- B32B 15/043: {of metal (B32B15/01 takes precedence)}
- B32B 15/082: comprising vinyl resins; comprising acrylic resins
- B32B 15/085: comprising polyolefins
- B32B 15/088: comprising polyamides
- B32B 15/09: comprising polyesters
- B32B 15/14: next to a fibrous or filamentary layer
- B32B 15/20: comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)}
- B32B 23/04: comprising such {cellulosic plastic} substance as the main or only constituent of a layer, {which is} next to another layer of {the same or of} a {different material (next to a glass layer B32B17/08)}
- B32B 23/042: {of metal}
- B32B 23/08: of synthetic resin
- B32B 23/10: next to a fibrous or filamentary layer
- B32B 27/08: of synthetic resin
- B32B 27/12: next to a fibrous or filamentary layer
- B32B 27/302: {comprising aromatic vinyl (co)polymers, e.g. styrenic (co)polymers}
- B32B 27/306: {comprising vinyl acetate or vinyl alcohol (co)polymers}
- B32B 27/308: {comprising acrylic (co)polymers}
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 27/34: comprising polyamides
- B32B 27/36: comprising polyesters
- C08G 18/12: using two or more compounds having active hydrogen in the first polymerisation step
- C08G 18/4018: {Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48}
- C08G 18/4202: {Two or more polyesters of different physical or chemical nature (C08G18/44 takes precedence)}
- C08G 18/4238: {derived from dicarboxylic acids and dialcohols}
- C08G 18/4288: {modified by higher fatty oils or their acids or by resin acids}
- C08G 18/4825: {Polyethers containing two hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/4829: {Polyethers containing at least three hydroxy groups (C08G18/4833 - C08G18/5096 take precedence)}
- C08G 18/7671: {containing only one alkylene bisphenyl group}
- C09J 175/08: from polyethers
- B32B 2307/31: Heat sealable
- B32B 2307/732: Dimensional properties
- B32B 2307/748: Releasability
- B32B 2439/70: Food packaging
- C09J 2301/12: by the arrangement of layers
- C09J 2301/30: characterized by the chemical, physicochemical or physical properties of the adhesive or the carrier
- C09J 2400/163: in the substrate
- C09J 2423/046: in the substrate
- C09J 2475/00: Presence of polyurethane
- 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)
- 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

## Abstract

The present disclosure provides a two-component solvent-less adhesive composition. The two-component solvent-less adhesive composition contains the reaction product of (A) an isocyanate component containing the reaction product of (i) an isocyanate monomer and (ii) a first dimer acid polyester polyol; and (B) a polyol component containing (i) a second dimer acid polyester polyol and (ii) optionally, a polyol selected from a polyether polyol, a polyester polyol, and combinations thereof. The two-component solvent-less adhesive composition contains from 15 wt % to 45 wt % units derived from dimer acid, based on the total weight of the two-component solvent-less adhesive composition.

## Claims

### Claim 1

A two-component solvent-less adhesive composition comprising the reaction product of:
(A) an isocyanate component comprising the reaction product of
(i) an isocyanate monomer;
(ii) a first dimer acid polyester polyol;
(B) a polyol component comprising
(i) a second dimer acid polyester polyol; and
(ii) optionally, a polyol selected from the group consisting of a polyether polyol, a polyester polyol, and combinations thereof;
the two-component solvent-less adhesive composition comprising from 15 wt % to 45 wt % units derived from dimer acid, based on the total weight of the two-component solvent-less adhesive composition.

### Claim 2 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the isocyanate component further comprises a second polyol selected from the group consisting of a polyether polyol, a polyester polyol, and combinations thereof.

### Claim 3 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the isocyanate component comprises the reaction product of
(i) from 45 wt % to 90 wt % of the isocyanate monomer;
(ii) from 10 wt % to 55 wt % of the first dimer acid polyester polyol; and
(iii) from 0 wt % to 30 wt % of a second polyol selected from the group consisting of a polyether polyol, a polyester polyol, and combinations thereof.

### Claim 4 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the polyol component comprises
(i) from 10 wt % to 50 wt % of the second dimer acid polyester polyol; and
(ii) from 50 wt % to 90 wt % of the polyether polyol.

### Claim 5 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the two-component solvent-less adhesive composition has an NCO Index from 1.0 to 1.8.

### Claim 6 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the two-component solvent-less adhesive composition has an NCO Index from 1.4 to 1.8.

### Claim 7 (depends on 1)

A laminate comprising
a first substrate;
a second substrate; and
an adhesive layer between the first substrate and the second substrate, the adhesive layer formed from the two-component solvent-less adhesive composition of claim 1.

### Claim 8 (depends on 7)

The laminate of claim 7, wherein the first substrate is a polyethylene film and the second substrate is a metal foil film; and the laminate has a bond strength after the boil-in-bag test from 1.0 N/15 mm to 15 N/15 mm.

### Claim 9 (depends on 8)

The laminate of claim 8, wherein the laminate has a heat seal strength after the boil-in-bag test from 20 N/15 mm to 75 N/15 mm.

### Claim 10

A method of forming a two-component solvent-less adhesive composition comprising:
(A) providing an isocyanate component comprising the reaction product of
(i) an isocyanate monomer;
(ii) a first dimer acid polyester polyol;
(B) providing a polyol component comprising
(i) a second dimer acid polyester polyol;
(ii) optionally, a polyol selected from the group consisting of a polyether polyol, a polyester polyol, and combinations thereof; and
(C) reacting the isocyanate component with the polyol component to form the two-component solvent-less adhesive composition comprising from 15 wt % to 45 wt % units derived from dimer acid, based on the total weight of the two-component solvent-less adhesive composition.

### Claim 11 (depends on 1)

The two-component solvent-less adhesive composition of claim 1, wherein the polyol is present in the polyol component; and
the polyol component has a hydroxyl value from 250 mg KOH/g to 300 mg KOH/g.

### Claim 12 (depends on 11)

The two-component solvent-less adhesive composition of claim 11, wherein the polyol is a polyether polyol.

### Claim 13 (depends on 10)

The method of claim 10 wherein the polyol is present in the polyol component; and
the polyol component has a hydroxyl value from 250 mg KOH/g to 300 mg KOH/g.

### Claim 14 (depends on 13)

The method of claim 13, wherein the polyol is a polyether polyol.

### Claim 15

A two-component solvent-less adhesive composition comprising the reaction product of:
(A) an isocyanate component comprising the reaction product of
(i) an isocyanate monomer;
(ii) a first dimer acid polyester polyol;
(B) a polyol component with a hydroxyl value from 250 mg KOH/g to 300 mg KOH/g, the polyol component comprising
(i) a second dimer acid polyester polyol; and
(ii) a polyol selected from the group consisting of a polyether polyol, a polyester polyol, and combinations thereof;
the two-component solvent-less adhesive composition comprising from 15 wt % to 45 wt % units derived from dimer acid, based on the total weight of the two-component solvent-less adhesive composition.

### Claim 16 (depends on 15)

The two-component solvent-less adhesive composition of claim 15, wherein the polyol is a polyether polyol.