Radiation curable laminating adhesives based on cycloaliphatic carboxylic acid functional monomers
Provided are radiation-cured, laminated materials, radiation-curable adhesive compositions suitable for use in forming the laminated materials, and methods of making laminated materials. The radiation-curable composition includes the use of a cycloaliphatic carboxylic acid functional monomer
1 - 60 . (canceled)
61 . A radiation-curable laminating adhesive composition comprising 10 to 90% by weight of at least one cycloaliphatic carboxylic acid functional monomer and 10 to 90% by weight of one or more radiation-curable, non-cycloaliphatic carboxylic acid functional monomers based on the total weight of the composition.
62 . The composition of claim 61 , wherein the at least one cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and hexahydrophthalic anhydride.
63 . The composition of claim 61 , wherein the at least one cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and substituted-hexahydrophthalic anhydride.
64 . The composition according to claim 63 , wherein the substituted-hexahydrophthalic anhydride comprises an alkyl-hexahydrophthalic anhydride.
65 . The composition according to claim 64 , wherein the alkyl-hexahydrophthalic anhydride comprises methylhexahydrophthalic anhydride.
66 . The composition according to claim 61 , wherein the non-cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and succinic anhydride.
67 . The composition according to claim 61 , further comprising at least 50% of one or more radiation-curable, carboxylic acid functional monomers.
68 . The composition according to claim 61 , wherein the composition consists essentially of radiation-curable carboxylic acid functional monomers.
69 . The composition according to claim 61 , wherein the cycloaliphatic carboxylic acid functional monomer is present in an amount of from about 20 to about 80% by weight of the total composition.
70 . The composition according to claim 61 , wherein the cycloaliphatic carboxylic acid functional monomer is present in an amount of from about 30 to about 70% by weight of the total composition.
71 . The composition according to claim 61 , further comprising from about 0.1 to about 10% by weight of at least one photoinitiator.
72 . The composition according to claim 71 , wherein at least one photoinitiator is a polymeric or a polymerizable compound.
73 . The composition according to claim 61 , further comprising at least one flow additive, anti-foaming additive, (meth)acrylate oligomer, non-carboxylic acid functional (meth)acrylate monomer, filler, pigment, dye, titanate compound, or resinous material.
74 . The composition according to claim 61 , wherein the cycloaliphatic carboxylic acid functional monomer is a cycloaliphatic carboxylic acid functional (meth)acrylate monomer.
75 . The composition according to claim 61 , wherein the composition is formulated for curing by EB radiation.
76 . The composition according to claim 61 , wherein the composition is formulated for curing by UV radiation.
77 . A radiation-curable laminating adhesive composition comprising:
10 to 90% by weight of at least one cycloaliphatic carboxylic acid functional monomer having a number average molecular weight of from about 100 to about 3000; and
10 to 90% by weight of one or more radiation-curable, non-cycloaliphatic carboxylic acid functional monomers by weight, the weight being based on the total weight of the composition, wherein the composition is formulated such that when suitably cured in a laminate migration of uncured monomers through layers of the laminate is substantially avoided.
78 . The composition of claim 77 , wherein the at least one cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and hexahydrophthalic anhydride.
79 . The composition of claim 77 , wherein the at least one cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and substituted-hexahydrophthalic anhydride.
80 . The composition according to claim 79 , wherein the substituted-hexahydrophthalic anhydride comprises an alkyl-hexahydrophthalic anhydride.
81 . The composition according to claim 80 , wherein the alkyl-hexahydrophthalic anhydride comprises methylhexahydrophthalic anhydride.
82 . The composition according to claim 77 , wherein the non-cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and succinic anhydride.
83 . The composition according to claim 77 , further comprising at least 50% of one or more radiation-curable, carboxylic acid functional monomers.
84 . The composition according to claim 77 , wherein the composition consists essentially of radiation-curable carboxylic acid functional monomers.
85 . The composition according to claim 77 , wherein the cycloaliphatic carboxylic acid functional monomer is present in an amount of from about 20 to about 80% by weight of the total composition.
86 . The composition according to claim 77 , wherein the cycloaliphatic carboxylic acid functional monomer is present in an amount of from about 30 to about 70% by weight of the total composition.
87 . The composition according to claim 77 , further comprising from about 0.1 to about 10% by weight of at least one photoinitiator.
88 . The composition according to claim 87 , wherein at least one photoinitiator is a polymeric or a polymerizable compound.
89 . The composition according to claim 77 , further comprising at least one flow additive, anti-foaming additive, (meth)acrylate oligomer, non-carboxylic acid functional (meth)acrylate monomer, filler, pigment, dye, titanate compound, or resinous material.
90 . The composition according to claim 77 , wherein the cycloaliphatic carboxylic acid functional monomer is a cycloaliphatic carboxylic acid functional (meth)acrylate monomer.
91 . The composition according to claim 77 , wherein the composition is formulated for curing by EB radiation.
92 . The composition according to claim 77 , wherein the composition is formulated for curing by UV radiation.
93 . A radiation-curable laminating adhesive composition comprising:
from 10 to 100% of at least one cycloaliphatic carboxylic acid functional monomer based on the total weight of the composition, and wherein the cycloaliphatic carboxylic acid functional monomer is the half-ester of 2-hydroxyethylacrylate and a substituted-hexahydrophthalic anhydride.
94 . The composition according to claim 93 , wherein the substituted hexahydrophthalic anhydride comprises alkyl-hexahydrophthalic anhydride.
95 . The composition according to claim 94 , wherein the alkyl-hexahydrophthalic anhydride comprises methylhexahydrophthalic anhydride.
96 . The composition according to claim 93 , comprising 10 to 90% of one or more radiation-curable, non-cycloaliphatic carboxylic acid functional monomers.
97 . The composition according to claim 96 , wherein the non-cycloaliphatic carboxylic acid functional monomer comprises the half ester of 2-hydroxyethyl acrylate and succinic anhydride.
98 . The composition according to claim 93 , comprising at least 50% of radiation-curable, carboxylic acid functional monomers.
99 . The composition according to claim 93 , wherein the composition consists essentially of radiation-curable carboxylic acid functional monomers.
100 . The composition according to claim 93 , wherein the cycloaliphatic carboxylic acid functional monomer is present in the composition in an amount of from about 20 to about 80% by weight of the total composition.
101 . The composition according to claim 93 , wherein the cycloaliphatic carboxylic acid functional monomer is present in the composition in an amount of from about 30 to about 70% by weight of the total composition.
102 . The composition according to claim 93 , further comprising from about 0.1 to about 10% by weight of at least one photoinitiator.
103 . The composition according to claim 102 , wherein at least one photoinitiator is a polymeric or a polymerizable compound.
104 . The composition according to claim 93 , further comprising at least one flow additive, anti-foaming additive, (meth)acrylate oligomer, non-carboxylic acid functional (meth)acrylate monomer, filler, pigment, dye, titanate compound, or resinous material.
105 . The composition according to claim 93 , wherein the cycloaliphatic carboxylic acid functional monomer is a cycloaliphatic carboxylic acid functional (meth)acrylate monomer.
106 . The composition according to claim 93 , wherein the composition is formulated for curing by EB radiation.
107 . The composition according to claim 93 , wherein the composition is formulated for curing by UV radiation.