Composition of vinyl ether group-containing (meth) acrylic acid ester and production method thereof

Abstract

It is an object of the present invention to provide a vinyl ether group-containing (meth) acrylic ester, which has both radical polymerizability and cation polymerizability, improved in storage stability and stability in handling without impairing its polymerizability or, in other words, provide a stabilized vinyl ether group-containing (meth) acrylic ester. Another object is to provide a method of producing a stabilized vinyl ether group-containing (meth) acrylic ester composition. A further object is to provide a method of stably handing, a method of economically and stably producing and a method of purifying a vinyl ether group-containing (meth) acrylic ester. A vinyl ether group-containing (meth) acrylic ester composition which comprises a radical polymerization inhibitor and a vinyl ether group-containing (meth) acrylic ester represented by the following general formula (1): CH2═CR1-COO—R2-O—CH—CH—R3   (1) in the formula, R1 represents a hydrogen atom or a methyl group, R2 represents an organic residue and R3 represents a hydrogen atom or an organic residue.

1 - 17 . (canceled) 
     
     
         18 . A method of transporting, storing or transferring a vinyl ether group-containing (meth)acrylic ester, which comprises transporting, storing or transferring said vinyl ether group-containing (meth)acrylic ester under the condition such that said vinyl ether group-containing (meth)acrylic ester is placed in a container and a molecular oxygen concentration in the gaseous phase in the container is 0.01 to 15% by volume and said vinyl ether group-containing (meth)acrylic ester being represented by the following formula (1):
   CH 2 ═CR 1 —COO—R 2 —O—CH═CH—R 3   (1)   in the formula, R 1  represents a hydrogen atom or a methyl group, R 2  represents a straight, branched or cyclic alkylene group containing 2 to 20 carbon atoms, an alkylene group containing 2 to 20 carbon atoms and having at least one oxygen atom in the form of an ether linkage and/or an ester linkage within the structure thereof, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted, and R 3  represents a hydrogen atom, a straight, branched or cyclic alkyl group containing 1 to 10 carbon atoms, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted.   
     
     
         19 . A method of producing a vinyl ether group-containing (meth)acrylic ester represented by the following formula (1):
   CH 2 ═CR 1 —COO—R 2 —O—CH═CH—R 3   (1)   in the formula, R 1  represents a hydrogen atom or a methyl group, R 2  represents a straight, branched or cyclic alkylene group containing 2 to 20 carbon atoms, an alkylene group containing 2 to 20 carbon atoms and having at least one oxygen atom in the form of an ether linkage and/or an ester linkage within the structure thereof, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted, and R 3  represents a hydrogen atom, a straight, branched or cyclic alkyl group containing 1 to 10 carbon atoms, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted,   which comprises reacting a hydroxyl group-containing vinyl ether represented by the following formula (2):
   R 3 —CH═CH—O—R 2 —OH  (2) 
   in the formula, R 2  represents a straight, branched or cyclic alkylene group containing 2 to 20 carbon atoms, an alkylene group containing 2 to 20 carbon atoms and having at least one oxygen atom in the form of an ether linkage and/or an ester linkage within the structure thereof, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted, and R 3  represents a hydrogen atom, a straight, branched or cyclic alkyl group containing 1 to 10 carbon atoms, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted,   with a (meth)acrylic ester represented by the following formula (3):
   CH 2 ═CR 1 —COOR 4   (3) 
   in the formula, R 1  represents a hydrogen atom or a methyl group and R 4  represents a straight, branched a cyclic alkyl group containing 1 to 8 carbon atoms,   in an atmosphere such that a molecular oxygen concentration is 0.01 to 10% by volume.   
     
     
         20 . A method of transporting, storing or transferring a vinyl ether group-containing (meth)acrylic ester which comprises transporting, storing or transferring said vinyl ether group-containing (meth)acrylic ester in a lightproof structure while keeping a molecular oxygen concentration in the gaseous phase within said lightproof structure at 0.01 to 22% by volume and said vinyl ether group-containing (meth)acrylic ester being represented by the following formula (1):
   CH 2 ═CR 1 —COO—R 2 —O—CH═CH—R 3   (1)   in the formula, R 1  represents a hydrogen atom or a methyl group, R 2  represents a straight, branched or cyclic alkylene group containing 2 to 20 carbon atoms, an alkylene group containing 2 to 20 carbon atoms and having at least one oxygen atom in the form of an ether linkage and/or an ester linkage within the structure thereof, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted, R 3  represents a hydrogen atom, a straight, branched or cyclic alkyl group containing 1 to 10 carbon atoms, or an aromatic group which contains 6 to 11 carbon atoms and may optionally be substituted.