Flexible polyureas for flexible packaging adhesive without aromatic amine migration

Patent metadata

Field	Value
Publication number	US-12037520-B2
Application number	US-202318335301-A
Country	US
Kind code	B2
Filing date	Jun 15, 2023
Priority date	Aug 8, 2019
Publication date	Jul 16, 2024
Grant date	Jul 16, 2024

Abstract

Provided is an adhesive comprising a reaction product of (A) an aliphatic polyisocyanate having a molecular weight of from 132 to 700; and (B) a polyaspartate comprising a reaction product of (B1) a polyamine having a molecular weight of at least 240, and (B2) a Michael addition receptor, wherein viscosity @ 23° C. according to ASTM D1084-16, remains below 150 cps after four hours, and wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than five days after the substrate is laminated with the adhesive. The inventive flexible packaging adhesives are free of aromatic amines and may find use in multilayer laminates for a variety of industries, including the food processing, cosmetics, and detergents industries.

First claim

What is claimed is:

1. A multi-layered laminated film comprising a layer of an adhesive applied to one or more substrate layers, the adhesive comprising a reaction product of:
(A) an aliphatic polyisocyanate having a number average molecular weight of from 132 to 700, wherein, if (A) includes a plurality of aliphatic polyisocyanates, the plurality of aliphatic polyisocyanates has a number average molecular weight of from 132 to 700; and
(B) a polyaspartate comprising a reaction product of:
(B1) a polyamine having a molecular weight of at least 240, and
(B2) a Michael addition receptor,
wherein the polyaspartate has a structure corresponding to formula (I)

wherein:
n is an integer of at least 2,
X is a C3 or C4 polyether having a molecular weight ≥208,
R 1 and R 2 each independently represent organic groups that are inert to isocyanate groups under reaction conditions, and
R 3 and R 4 each independently represent hydrogen or organic groups that are inert to isocyanate groups under reaction conditions,

wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than five days after the substrate is laminated with the adhesive.

2. The multi-layered laminated film according to claim 1 , wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in from one to five days after the substrate is laminated with the adhesive.

3. The multi-layered laminated film according to claim 1 , wherein the adhesive develops an acceptable bond strength to a substrate, defined as having a minimum of 150 g/in. measured @ 23° C. according to ASTM D 1876-01 or substrate tear, in less than one day after the substrate is laminated with the adhesive.

4. The multi-layered laminated film according to claim 1 , wherein the aliphatic polyisocyanate (A) is selected from the group consisting of 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 1,5-pentamethylene diisocyanate, 2,2,4- and/or 2,4,4-trimethyl-hexamethylene diisocyanate, dodecamethylene diisocyanate, 2-methyl-1,5-diisocyanatopentane, 1,4-diisocyanatocyclohexane, 5-isocyanato-1-(isocyanatomethyl)-1,3,3-trimethylcyclohexane, 2,4- and/or 4,4′ diisocyanato-dicyclohexyl-methane, 1-isocyanato-1-methyl-3(4)-isocyanatomethyl-cyclohexane, 1,4-cyclohexane diisocyanate, and trimers, isocyanurates, uretdiones, biurets, allophanates, iminooxadiazine diones, carbodiimides, oxadiazine triones, and prepolymers of any of these, and mixtures thereof.

5. The multi-layered laminated film according to claim 1 , wherein the polyamine (B1) has a molecular weight of from 240 and 6000.

6. The multi-layered laminated film according to claim 1 , wherein the polyamine (B1) has a molecular weight of from 400 to 2000.

7. The multi-layered laminated film according to claim 1 , wherein the Michael addition receptor (B2) is selected from the group consisting of dimethyl maleate, diethyl maleate, dibutyl maleate, dimethyl fumarate, diethyl fumarate, dibutyl fumarate, acrylates, and combinations thereof.

8. The multi-layered laminated film according to claim 1 , wherein each layer independently has a thickness of from 5 μm to 250 μm, and wherein the multi-layered laminated film has a total thickness of from 20 μm to 750 μm.

9. The multi-layered laminated film according to claim 1 , wherein the one or more substrate layers are independently selected from the group consisting of paper, metal and thermoplastic polymers.

10. The multi-layered laminated film according to claim 9 , wherein the metal is selected from the group consisting of aluminum, copper, and steel.

11. The multi-layered laminated film according to claim 9 , wherein the thermoplastic polymer is independently selected from the group consisting of polyethylene, corona-treated polyethylene, polyethylene terephthalate, corona-treated polyethylene terephthalate, metalized polyethylene terephthalate, polypropylene, and corona-treated polypropylene.

12. A flexible packaging material comprising the multi-layered laminated film according to claim 1 .

Assignees

• Covestro Llc

Inventors

• Haider Karl W
• Zeliznik Raymond
• Jones Philip

Classifications

• B32B15/20

  comprising aluminium or copper {(B32B15/016 and B32B15/017 take precedence)} · CPC title

• B32B2307/546

  Flexural strength; Flexion stiffness · CPC title

• B32B27/32

  comprising polyolefins {(comprising vinyl (co)polymers or acrylic (co)polymers B32B27/30)} · CPC title

• C08G18/73 Primary

  acyclic · CPC title

• C08G18/10

  Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step · CPC title