Two-component polyurethane adhesive composition for film lamination

Patent metadata

Field	Value
Publication number	US-12577447-B2
Application number	US-202118578945-A
Country	US
Kind code	B2
Filing date	Jul 16, 2021
Priority date	Jul 16, 2021
Publication date	Mar 17, 2026
Grant date	Mar 17, 2026

Abstract

The present invention relates to a two-component polyurethane adhesive composition for film lamination, in particular in food flexible packaging. Further, the present invention relates to method of manufacturing a laminate by using the two-component polyurethane adhesive composition and the laminate obtainable by the described method.

First claim

The invention claimed is:

1 . A two-component polyurethane adhesive composition comprising a polyol component and an isocyanate component, wherein
the polyol component comprises at least one polyester polyol obtained from a reaction mixture comprising, based on the total weight of the reaction mixture,
from 1% to 25% by weight of at least one cycloaliphatic polyol,
from 1% to 40% by weight of at least one heterocyclic polyol,
from 1% to 40% by weight of at least one linear or branched aliphatic polyol, and
from 30% to 70% by weight of at least one polyfunctional carboxylic acid, and
the isocyanate component comprises at least one alkoxysilane functionalized isocyanate compound having no epoxide group, wherein the cycloaliphatic polyol is selected from 1,4-cyclohexanedimethanol, cyclobutanediol, cyclopentanediol, 1,4-cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol, tricyclo[5.2.1.0.2.6]decanedimethanol, bicyclo[4.3.0]-nonanediol, dicyclohexanediol, tricyclo[5.3.1.1]dodecanediol, bicyclo[4.3.0]nonanedimethanol, tricyclo[5.3.1.1]dodecanediethanol, spiro[3.4]octanediol, butylcyclohexanediol, 1,1′-bicyclohexylidenediol, cyclohexanetriol, hydrogenated bisphenol A, 1,3-adamantanediol, and mixtures thereof.

2 . The adhesive composition according to claim 1 , wherein, the heterocyclic polyol is selected from 1,4:3,6-dianhydrohexitol, spiroglycol, 2,4:3,5-di-O-methylenemannitol, and 2,3:4,5-di-O-methylenegalactose.

3 . The adhesive composition according to claim 1 , wherein the alkoxysilane functionalized isocyanate compound is a reaction product of at least one aliphatic or alicyclic isocyanate-functionalized compound and at least one hydrolyzable alkoxysilane compound having no epoxide group.

4 . The adhesive composition according to claim 3 , wherein the hydrolyzable alkoxysilane compound having no epoxide group comprises a functional group selected from hydroxy group, thiol group, carboxyl group, primary amino group, secondary amino group, and mixture thereof.

5 . The adhesive composition according to claim 3 , wherein the aliphatic or alicyclic isocyanate-functionalized compound is selected from 1,6-hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI), xylyl diisocyanate (XDI), an adduct thereof, an oligomer thereof, and a mixture of above.

6 . The adhesive composition according to claim 3 , wherein the hydrolyzable alkoxysilane compound having no epoxide group comprises a functional group that is reactive toward isocyanate groups.

7 . The adhesive composition according to claim 1 , wherein the hydrolyzable alkoxysilane compound having no epoxide group is selected from α-aminomethyltrimethoxysilane, α-aminomethylmethyldimethoxysilane, α-aminomethyldimethylmethoxysilane, α-aminomethyltriethoxysilane, α-aminomethylmethyldiethoxysilane, α-aminomethyldimethylethoxysilane, γ-aminopropyltrimethoxysilane, γ-aminopropylmethyldimethoxysilane, γ-aminopropyldimethylmethoxysilane, γ-aminopropyltriethoxysilane, γ-aminopropylmethyldiethoxysilane, γ-aminopropyldimethylethoxysilane, N-2(aminoethyl)α-aminomethyltrimethoxysilane, N-2(aminoethyl)α-aminomethylmethyldimethoxysilane, N-2(aminoethyl)α-aminomethyldimethylmethoxysilane, N-2(aminoethyl)α-aminomethyltriethoxysilane, N-2(aminoethyl)α-aminomethylmethyldiethoxysilane, N-2(aminoethyl)α-aminomethyldimethylethoxysilane, bis-(trimethoxysilylpropyl) amine, bis-(methyldimethoxysilylpropyl) amine, bis-(dimethylmethoxysilylpropyl) amine, bis-(triethoxysilylpropyl) amine, bis-(methyldiethoxysilylpropyl) amine, bis-(dimethylethoxysilyipropyl) amine, and mixture thereof.

8 . The adhesive composition according to claim 1 , wherein the isocyanate component further comprises at least one aliphatic or alicyclic isocyanate-functionalized compound.

9 . The adhesive composition according to claim 1 , wherein the adhesive composition comprises one or more additives selected from the group consisting of solvents, catalysts, thermal plastic resins, deformers, plasticizers, compatible tackifiers, fillers, antioxidants, pigments, stabilizers, waxes, and mixture thereof.

10 . A cured adhesive obtainable by curing an adhesive composition according to claim 1 .

11 . The cured adhesive according to claim 10 , having a bonding strength to polyethylene of no less than 3 N/15 mm after being stored at 40° C. for 7 days according to DIN 53357.

12 . The cured adhesive according to claim 10 , having a bonding strength to polyethylene of no less than 3 N/15 mm after stored at 40° C. for 7 days and sterilized at 131° C. for 30 min according to DIN 53357.

13 . The cured adhesive according to claim 10 , having a bonding strength to polyethylene of no less than 3 N/15 mm after stored at 40° C. for 7 days and sterilized with oleic acid at 131° C. for 30 min according to DIN 53357.

14 . A flexible packaging material comprising a first layer comprised of a first polyolefin or first polyester; a second layer comprised of a second foil, a third layer comprised of a polyolefin which may be the same or different from the first polyolefin, a second polyester which may be the same as or different from the first polyester, or a metal foil; and cured reaction products of the two-component polyurethane adhesive of claim 1 bonding the second layer to the third layer.

15 . A method of making a flexible film laminate, comprising:
combining the components of the two-component polyurethane adhesive composition according to claim 1 at a predetermined weight ratio to form an adhesive mixture, disposing the adhesive mixture on at least a portion of one surface of a first flexible film, joining the first flexible film and a second flexible film wherein the adhesive mixture is interposed between the first flexible film and the second flexible film; and curing the adhesive mixture.

16 . The adhesive composition according to claim 1 , wherein the heterocyclic polyol is isosorbide.

Assignees

• Henkel Ag & Co Kgaa

Inventors

• Blodau Marcel
• Franken Marcel
• Tomke Stefan
• Flores Penalba Sonia
• Eckstein Andrea

Classifications

• C09J2475/00

  Presence of polyurethane · CPC title

• C09J5/00

  Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers · CPC title

• C08G18/792

  formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates · CPC title

• C08G18/755

  and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate · CPC title

• C08G18/4216

  from mixtures or combinations of aromatic dicarboxylic acids and aliphatic dicarboxylic acids and dialcohols · CPC title