Polyurethane adhesive composition for film lamination

1 . A polyurethane adhesive composition comprising:

a polyol component comprising 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

an isocyanate component comprising the combination of at least one aliphatic or alicyclic isocyanate-functionalized compound and at least one hydrolyzable alkoxysilane compound having no epoxide group, and/or the reaction product of at least one aliphatic or alicyclic isocyanate-functionalized compound and at least one hydrolyzable alkoxysilane 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 polyurethane 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, and preferably is isosorbide.

3 . The polyurethane adhesive composition according to claim 1 , 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.

4 . The polyurethane adhesive composition according to claim 1 , wherein the hydrolyzable alkoxysilane compound having no epoxide group comprises a functional group that is reactive toward isocyanate groups.

5 . The polyurethane 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.

6 . The polyurethane adhesive composition according to claim 1 , wherein the ratio by weight of the polyol and isocyanate components is from 15:1 to 1:5.

7 . A one-, two- or multiple-part polyurethane adhesive system comprising a polyurethane prepolymer being the reaction product of the polyurethane adhesion composition according to claim 1 .

8 . A two- or multiple-part polyurethane adhesive system comprising the polyurethane adhesive composition according to claim 1 .

9 . The two- or multiple-part polyurethane adhesive system according to claim 8 , wherein the polyurethane adhesive system comprises at least one solvent or comprises no solvent.

10 . The two- or multiple-part polyurethane adhesive system according to claim 8 wherein the polyurethane adhesive composition is cured and has 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.

11 . The two- or multiple-part polyurethane adhesive system according to claim 8 wherein the polyurethane adhesive composition is cured and has a bonding strength to polyethylene of no less than 5 N/15 mm after stored at 40° C. for 7 days and sterilized at 131° C. for 30 min according to DIN 53357.

12 . The two- or multiple-part polyurethane adhesive system according to claim 8 , wherein the polyurethane adhesive composition is cured and has a bonding strength to polyethylene of no less than 5 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.

13 . A flexible packaging material comprising a first layer comprised of a first polyolefin or first polyester; a second layer comprised of a second 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 a cured reaction product of the polyurethane adhesion composition according to claim 1 bonding the first layer to the second layer.

14 . A method of making a flexible film laminate, comprising:

combining the components of 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.