# US 11,078,382 B2 · Two-component solventless adhesive compositions comprising an amine-initiated polyol

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- Number: US 11,078,382 B2
- Document ID: US11078382B2
- Status: Granted
- Kind: B2
- Application number: 16/300,560
- Filed: 2017-04-25
- Published: 2019-06-13
- Granted: 2021-08-03
- Earliest claimed: 2016-05-10
- Assignees: Dow Global Technologies LLC
- Applicants: Dow Global Technologies LLC
- Inventors: Jie Wu; Rui Xie; Kalyan Sehanobish
- Web page: https://patentgrep.com/patent/US11078382B2

## CPC

- C09J 5/04: involving separate application of adhesive ingredients to the different surfaces to be joined
- B32B 5/022: {Non-woven fabric}
- B32B 5/024: {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 15/043: {of metal (B32B15/01 takes precedence)}
- B32B 15/08: of synthetic resin
- B32B 15/10: of wood
- B32B 15/12: of paper or cardboard
- B32B 15/14: next to a fibrous or filamentary layer
- B32B 21/042: {of wood (B32B21/13 takes precedence)}
- B32B 21/06: of paper or cardboard
- B32B 21/08: of synthetic resin
- B32B 21/10: Next to a fibrous or filamentary layer
- B32B 27/08: of synthetic resin
- B32B 27/10: of paper or cardboard
- B32B 27/12: next to a fibrous or filamentary layer
- B32B 27/32: comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)}
- B32B 29/005: {next to another layer of paper or cardboard layer}
- B32B 29/02: next to a fibrous or filamentary layer
- C08G 18/5021: {having nitrogen}
- C08G 18/76: aromatic
- C09J 175/00: Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J 175/04: Polyurethanes
- B32B 2255/10: on synthetic resin layer or on natural or synthetic rubber layer
- B32B 2255/205: Metallic coating
- B32B 2307/306: Resistant to heat
- B32B 2307/714: Inert, i.e. inert to chemical degradation, corrosion
- B32B 2439/70: Food packaging
- B32B 2597/00: Tubular articles, e.g. hoses, pipes
- C08G 18/4277: {Caprolactone and/or substituted caprolactone}
- C08G 18/44: Polycarbonates
- 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

A two-component solventless adhesive composition is disclosed, the adhesive composition comprising an isocyanate component comprising at least one isocyanate, and a polyol component comprising at least one amine-initiated polyol having a functionality of from 3 to 8 and a hydroxyl number of from 20 to 1,000, wherein the first and second components are formulated to be applied to separate substrates before being brought together. Further, a method for forming a laminate is disclosed, the method comprising uniformly applying the isocyanate component to a first substrate, uniformly applying the polyol component to a second substrate, bringing the first and second substrates together, thereby mixing and reacting the isocyanate component and the polyol component to form an adhesive between the first and second substrates, and curing the adhesive to bond the first and second substrates. Still further, a laminate formed by the method is disclosed.

## Claims

### Claim 1

A non-premixed two-component solventless laminating adhesive composition for use in food packaging laminates, comprising:
an isocyanate component comprising at least one isocyanate, the isocyanate component having film forming properties allowing for a uniform film thickness of 0.5 to 2.5 μm when applied to a first substrate; and
a polyol component comprising at least one amine-initiated polyol having a functionality of from 3 to 8 and a hydroxyl number of from 20 to 1,000, the polyol component having film forming properties allowing for a uniform film thickness of 0.5 to 2.5 μm when applied to a second substrate;
wherein the film thicknesses of the components control the stoichiometric ratio of components in the adhesive composition when the films are brought together for mixing and reacting, such that the stoichiometric ratio of the isocyanate component to the polyol component ranges from 1:1 to 3:1.

### Claim 2 (depends on 1)

The non-premixed two-component solventless laminating adhesive composition of claim 1, wherein the at least one isocyanate is selected from the group consisting of a monomeric isocyanate, a polymeric isocyanate, an isocyanate prepolymer, and combinations of two or more thereof.

### Claim 3 (depends on 1)

The non-premixed two-component solventless laminating adhesive composition of claim 1, wherein the at least one isocyanate is selected from the group consisting of hexamethylene diisocyanate (“HDI”) and isomers thereof, isophorone diisocyanate (“IPDI”) and isomers thereof, norbornane diisocyanate (“NBDI”) and isomers thereof, tetramethylxylylene diisocyanate (“TMXDI”) and isomers thereof, xylylene diisocyanate (“XDI”) and isomers thereof, toluene diisocyanate (“TDI”) and isomers thereof, diphenylmethane diisocyanate (“MDI”) and isomers thereof, isocyanate prepolymers thereof, and combinations of two or more thereof.

### Claim 4 (depends on 1)

The non pre-mixed two-component solventless laminating adhesive composition of claim 1, wherein the amine-initiated polyol is the reaction product of a C1-C6 alkylene oxide and an amine.

### Claim 5 (depends on 4)

The non-premixed two-component solventless laminating adhesive composition of claim 4, wherein the amine is selected from the group consisting of toluene diamine, methylamine, ethylenediamine, diethylenetriamine, aniline, aminoethylethanolamine, bis-3-aminopropylmethylamine, propylenediamine, tetra-hexamethyleneamine, triethanolamine, phenylenediamine, and combinations of two or more thereof.

### Claim 6 (depends on 1)

The non-premixed two-component solventless laminating adhesive composition of claim 1, wherein the amine-initiated polyol accounts for 0.5 to 20 wt % of the adhesive composition, based on the total weight of the adhesive composition.

### Claim 7 (depends on 1)

The non-premixed two-component solventless laminating adhesive composition of claim 1, the polyol component further comprising at least one non-amine-initiated polyol selected from the group consisting of a polyester polyol, a polyether polyol, a polycarbonate polyol, a polyacrylate polyol, a polycaprolactone polyol, a polyolefin polyol, a natural oil polyol, and combinations of two or more thereof.

### Claim 8 (depends on 1)

The non-premixed two-component solventless laminating adhesive composition of claim 1, further comprising an additive selected from the group consisting of a tackifier, a plasticizer, a rheology modifier, an adhesion promoter, an antioxidant, a filler, a colorant, a surfactant, a catalyst, and combinations of two or more thereof.

### Claim 9

A method for forming a laminate, comprising:
uniformly applying an isocyanate component having film forming properties to a first substrate at a film thickness of 0.5 to 2.5 μm, the isocyanate component comprising at least one isocyanate; and
uniformly applying a polyol component having film forming properties to a second substrate at a film thickness of 0.5 to 2.5 μm, the polyol component comprising at least one amine-initiated polyol having a functionality of from 3 to 8 and a hydroxyl number of from 20 to 1,000;
bringing the first and second substrates together, thereby mixing and reacting the isocyanate component and the polyol component to form an adhesive composition between the first and second substrates, wherein the film thicknesses of the components control the stoichiometric ratio of components in the adhesive composition when the films are brought together for mixing and reacting, such that the stoichiometric ratio of the isocyanate component to the polyol component ranges from 1:1 to 3:1; and
curing the adhesive to bond the first and second substrates,
wherein the adhesive comprises a viscosity greater than 10,000 mPa·s (at 40° C.) within 10 minutes after bringing the first and second substrates together.

### Claim 10 (depends on 9)

The method for forming a laminate of claim 9, wherein the amine-initiated polyol is the reaction product of a C1-C6 alkylene oxide and an amine.

### Claim 11 (depends on 10)

The method for forming a laminate of claim 10, wherein the alkylene oxide is selected from the group consisting of ethylene oxide, propylene oxide, 1,2-butylene oxide, and combinations of two or more thereof.

### Claim 12 (depends on 10)

The method for forming a laminate of claim 10, wherein the amine is selected from the group consisting of toluene diamine, methylamine, ethylenediamine, diethylenetriamine, aniline, aminoethylethanolamine, bis-3-aminopropylmethylamine, propylenediamine, tetra-hexamethyleneamine, triethanolamine, phenylenediamine, and combinations of two or more thereof.

### Claim 13 (depends on 9)

The method for forming a laminate of claim 9, wherein the amine-initiated polyol accounts for 0.5 to 20 wt % of the adhesive composition, based on the total weight of the adhesive composition.

### Claim 14 (depends on 9)

The method for forming a laminate of claim 9, the polyol component further comprising at least one non-amine-initiated polyol selected from the group consisting of a polyester polyol, a polyether polyol, a polycarbonate polyol, a polyacrylate polyol, a polycaprolactone polyol, a polyolefin polyol, a natural oil polyol, and combinations of two or more thereof.

### Claim 15 (depends on 9)

The method for forming a laminate of claim 9, further comprising adding an additive to the adhesive composition, the additive selected from the group consisting of a tackifier, a plasticizer, a rheology modifier, an adhesion promoter, an antioxidant, a filler, a colorant, a surfactant, a catalyst, a solvent, and combinations of two or more thereof.

### Claim 16 (depends on 9)

The method for forming a laminate of claim 9, wherein the first substrate and second substrate are each selected from the group consisting of wood, metal, plastics, composite materials, paper, fabric, and combinations of two or more thereof.

### Claim 17 (depends on 9)

A laminate formed by the method of claim 9.