US 7,321,051 B2
Composition of vinyl ether group-containing (meth) acrylic ester and production method thereof
Keiji Yurugi, Osaka (Japan); and Hiroko Yamaguchi, Osaka (Japan)
Assigned to Nippon Shokubai Co., Ltd., Osaka (Japan)
Filed on Oct. 22, 2001, as Appl. No. 9/982,861.
Claims priority of application No. 2000-322575 (JP), filed on Oct. 23, 2000.
Prior Publication US 2002/0143120 A1, Oct. 03, 2002
Int. Cl. C07C 69/52 (2006.01)
U.S. Cl. 560—205  [560/220] 3 Claims
 
1. A method of producing a vinyl ether group-containing (meth) acrylic ester represented by the following 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 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, R3 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, and which comprises reacting a hydroxyl group-containing vinyl ether represented by the following formula (2):
R3—CH═CH—O—R2—OH  (2)
in the formula, R2 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 R3 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):
CH2═CR1—COOR4  (3):
in the formula, R1 represents a hydrogen atom or a methyl group and R4 represents a straight, branched or cyclic alkyl group containing 1 to 8 carbon atoms and at least one compound selected from the group consisting of a divinyl ether represented by the following formula (4):
R3—CH═CH—O—R2—O—CH═CH—R3  (4)
in the formula, R2 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 the two R3 groups are the same or different and each 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,
a 2-substituted-1,3-dioxo compound represented by the following formula (5):

OG Complex Work Unit Drawing
in the formula, R2 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 R3 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, and
an unsaturated bond-containing vinyl ether represented by the following formula (6):
R3—CH═CH—O—R5 (6)
in the formula, R3 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; R5 represents an organic residue containing an unsaturated bond represented by —CR6═CR7; and R6 and R7 are the same or different and each represents a hydrogen atom or an organic residue.