Toughened cyanoacrylate adhesives containing alkene-acrylate copolymers and method for production
AssigneeHenkel Corporation
InventorsJohn Woods, Susanne Morrill
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Abstract
A toughened cyanoacrylate adhesive composition including a cyanoacrylate monomer and an elastomeric copolymer soluble in the monomer, the copolymer being the reaction product of an olefin C2-20 and a (meth)acrylate ester. The invention further discloses novel elastomeric copolymers which do not contain additives or functional groups which can interfere with the cure rate or stability of the adhesive composition in which they are included. Benefits of the copolymers include improved toughness of the cured adhesive composition as measured by Dynamic Mechanical Analysis.
Claims31
A toughened cyanoacrylate adhesive composition substantially free of acidic or basic impurities comprising:
- (i) at least one cyanoacrylate monomer
- (ii) an elastomeric copolymer toughening additive substantially soluble in said cyanoacrylate monomer, said copolymer being the reaction product of an olefin C2-20 and a (meth)acrylate ester and being substantially free of acidic functionalities and acidic or basic impurities, wherein said olefin C2-20 has at least six carbon atoms.
A composition substantially free of acidic or basic impurities useful for toughening adhesives, comprising the reaction product of an olefin C2-20 and a (meth)acrylate ester, said reaction product being substantially free of acidic functionalities and acidic or basic impurities, wherein said olefin C2-20 has at least six carbon atoms.
A process for preparing a curable toughened cyanoacrylate adhesive composition, said composition comprising at least one cyanoacrylate monomer and a copolymer toughening additive substantially free of acidic functionally and acidic or basic impurities and soluble in said cyanoacrylate monomer, said copolymer toughening additive being substantially free of acidic functionalities and acidic or basic impurities and being the reaction product of a (meth)acrylate ester and an olefin C2-20, said process comprising the steps of:
- (a) combining said cyanoacrylate monomer with said copolymer toughening additive;
- and
- (b) subjecting said combined ingredients to conditions sufficient to allow said cyanoacrylate monomer to substantially solvate said copolymer.
A process for copolymerizing a (meth)acrylic ester with an olefin C2-20, wherein said olefin C2-20 has at least six carbon atoms the copolymerized product being substantially free of acidic functionality and acidic or basic impurities, said process comprising the steps of:
- (a) admixing a (meth)acrylic ester, a greater than equimolar amount of a Lewis acid per mole of said (meth)acrylic ester, a free radical initiator and an olefin C2-20 wherein said olefin C2-20 has at least six carbon atoms, and
- (b) heating at a temperature from about 60 to about 80° C. for a time sufficient to permit copolymerization of said ester with said olefin, the mole ratio of said olefin to said (meth)acrylic ester being from about 0.1 to about 10.
A process for esterifying an olefin/(meth)acrylate copolymer or olefin/alkenoic acid copolymer, the esterified product being substantially free of acidic functionality and acidic or basic impurities, said process comprising the steps of:
- (a) reacting said olefin/(meth)acrylate copolymer or said olefin/alkenoic acid copolymer with an alcohol in the presence of a catalytically effective amount of an acid catalyst at a temperature of about 50 to about 180° C. and in the presence of a solvent which is capable of dissolving said copolymer and which is suitable for esterification processes for a time sufficient to convert carboxylic acid functionalities on said copolymer into ester functionalities;
- and
- (b) removing said catalyst from said copolymer following esterification.
Dependencies are inferred from the claim text.