Reactive diluent and curable resin composition

Details Reactive diluent and curable resin composition Reactive diluent and curable resin composition

2002-04-19

2004-07-27

Zalukaeva, Tatyana (Department: 1713)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Polymers from only ethylenic monomers or processes of...

C526S219000, C526S237000, C526S272000, C525S330300, C525S330400, C525S330500, C525S387000, C554S167000, C554S223000, C554S224000, C554S227000

Reexamination Certificate

active

06767980

ABSTRACT:

FIELD OF THE INVENTION
The present invention relates to a reactive diluent composition, a curable resin composition containing the same, and uses of them. More particularly, the invention relates to a reactive diluent composition for curable resins which may be cured by heating or irradiation with an activated energy ray, a curable resin composition containing said reactive diluent composition, an activated energy ray-curable resin composition, and an activated energy ray-curable ink composition for ink-jet printing.
PRIOR ART
In the curing technology utilizing heat or an activated energy ray such as ultraviolet rays, an electron beam, or the like, a solventless curable composition employing a reactive diluent in lieu of the conventional organic solvent is attracting attention. Activated energy ray curing, in particular, is energy saving, space saving, and timesaving, to mention a few of its advantages, so that its scope of use is expanding.
Among constituent members of a curable resin composition, a polymerizable monomer used for reducing the viscosity and enhancing the adhesiveness of the resin composition, among other purposes, is known as a reactive diluent and a variety of such polymerizable monomers have been developed.
The reactive diluents so far developed can be classified into two types, namely the radical-cure type, represented by (meth)acrylic esters and vinyl compounds, and the cationic-cure type, represented by vinyl ethers, epoxy compounds, and alicyclic ethers.
But reactive diluents of the radical-cure type generally are disadvantageous in that 1) these are subject to the inhibition of polymerization by oxygen, 2) undergo a marked shrinkage in volume on curing, 3) have intense odors and a high skin-irritating potential, and 4) are somewhat poor in the adhesion to metals. Reactive diluents of the cationic cure type are disadvantageous in that 1) these are susceptible to polymerization inhibition due to moisture and bases, 2) the polymerization reaction continues to proceed even after the irradiation with ray (dark reaction), 3) the cationically curable resin and the catalyst required are expensive, and 4) the species commercially available are limited, among other drawbacks. Therefore, a reactive diluent free of the above disadvantages has been demanded.
Japanese Kohyo Publication Hei-07-505439 is directed to a radiation-curable coating composition comprising (a) a (meth)acryloyl group-containing polyfunctional acrylate oligomer or monomer; (b) a vinyl ether monomer, and (c) an effective amount of a free radical initiator. Thus, this literature discloses the use of a radically curable acrylate and a cationically curable vinyl ether in combination. But the mere such combination is unable to fully overcome the above-mentioned disadvantages of reactive diluents, and there is a room for devising.
SUMMARY OF THE INVENTION
Having been developed in the above state of the art, the present invention has a object to provide a reactive diluent composition which overcomes the drawbacks of both the radical-cure and the cationic-cure reactive diluents and can be applied in a broad variety of uses such as paints, inks, adhesives, pressure sensitive adhesives, surface modifiers, and molding materials; a curable resin composition containing the same; an activated energy ray-curable resin composition; and an activated energy ray-curable ink composition for ink-jet printing.
The inventors of the present invention made various investigations about reactive diluents and found that by using a vinyl ether group-containing (meth)acrylic ester containing a cationic-cure vinyl ether group and a radical-cure (meth)acryloyl group within each molecule and a hydroxyl-containing polymerizable compound and/or a divinyl ether in combination, not only the above-mentioned drawbacks of the radical-cure reactive diluent having only a radical-curable group and those of the cationic-cure reactive diluent having only a cationically curable group can be overcome but there can be obtained a cured artifact with better curability, improved adhesion to the substrate, and better surface hardness and solvent resistance than the cured artifact obtainable by using said radical-cure reactive diluent and cationic-cure reactive diluent as an admixture or by using a vinyl ether group-containing (meth)acrylic ester alone. It has also been found that even in the case of a reactive diluent composition comprising the vinyl ether group-containing (meth)acrylic ester of general formula (1), which is obtainable by subjecting a hydroxyl group-containing vinyl ether and a (meth)acrylic ester to transesterification reaction, said hydroxyl group-containing polymerizable compound and divinyl ether come into existence so that the same operation and effect as above can be obtained. Furthermore, a curable resin composition comprising such a reactive diluent composition comprising a vinyl ether group-containing (meth)acrylic ester and a hydroxyl group-containing polymerizable compound and/or a divinyl ether or a vinyl ether group-containing (meth)acrylic ester prepared by said transesterification reaction and a curable resin having at least one heat-curable or activated energy ray-curable polymeric group and an activated energy ray-curable resin composition comprising said reactive diluent composition are excellent in curability and can be improved adhesion, so that these can be used with advantage in various applications. Furthermore, it has been found that such reactive diluent compositions are suitable for use as an ingredient of the activated energy ray-curable ink for ink-jet printing use and that an activated energy ray-curable ink composition for ink-jet printing use which contains such a reactive diluent composition has many advantages such as low viscosity, low odor, low skin-irritating, good stability and high sensitivity to
as well as excellent curability and is very satisfactory in post-printing fundamental characteristics. The present invention has been developed on the basis of the above findings.
While the curable resin for use in the present invention is comprised of a macromonomer or prepolymer, a form of the macromonomer or prepolymer is not particularly restricted but includes such as a solid (powder), a liquid and so forth. The preferred form of said reactive diluent composition is liquid (a liquid state) at 25° C.
DETAILED DESCRIPTION OF THE INVENTION
The present invention is now described in detail.
The reactive diluent composition according to the present invention comprises
a vinyl ether group-containing (meth)acrylic ester represented by the following general formula (1):
CH
2
═CR
1
—COO—R
2
—O—CH═CH—R
3
  (1)
wherein R
1
represents a hydrogen atom or a methyl group; R
2
represents an organic residue of 2 to 20 carbon atoms; R
3
represents a hydrogen atom or an organic residue of 1 to 11 carbon atoms
and a hydroxyl group-containing polymerizable compound.
The vinyl ether group-containing (meth)acrylic ester for use as a component of the reactive diluent composition according to the present invention may be any compound that can be represented by the above general formula (1), wherein the substituent R
1
is hydrogen or methyl, the substituent R
2
is an organic residue containing 2 to 20 carbon atoms, and the substituent R
3
is hydrogen or an organic residue containing 1 to 11 carbon atoms. Such vinyl ether group-containing (meth)acrylic esters can be used each independently or in a combination of two or more species.
The organic residue of 2 to 20 carbon atoms as represented by R
2
in the above general formula (1) is preferably a linear, branched, or cyclic alkylene group of 2 to 20 carbon atoms, an alkylene group of 2 to 20 carbon atoms and an oxygen atom in the form of an ether bond and/or an ester bond, or an aromatic group containing 6 to 11 carbon atoms which may optionally be substituted. Among these, an alkylene group of 2 to 6 carbon atoms or an alkylene group containing 2 to 9 carbon atoms and an oxygen atom in the form of an ether bond can be used with advantage.
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