Saccharide-derived monomer, method for manufacturing the...

Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...

Reexamination Certificate

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C526S266000, C526S297000

Reexamination Certificate

active

06541587

ABSTRACT:

BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to a saccharide-derived monomer, to a method for manufacturing the same and to a highly-dielectric polymer consisting of the said monomer. More particularly, it relates to a highly dielectric polymer especially having a high dielectric constant and an excellent resistance to hygroscopicity useful as a solid electrolyte in the use as a binder for electroluminescence (EL) element, a film condenser dielectric material, polymer batteries, an electrochromic element, an electrolytic condenser, an electric double layer condenser, lithium ion secondary batteries, etc. and also to a saccharide-derived monomer giving the said monomer as well as a method for manufacturing the same.
2. Description of the Related Art
Organic electronic materials such as a binder for EL elements of a dispersed type are requested to have characteristics such as high dielectric property, low hygroscopicity for making their life long, unchangeability of electric characteristic values upon temperature change (heat resistance), and high adhesion to fluorescent substances and electrode surfaces. Under such circumstances, examples of the organic polymer used for a binder for EL elements of a dispersed type are (1) cyanoethylated products of polymers having many hydroxyl groups such as polyvinyl alcohol, cellulose or derivatives thereof and pullulan, (2) homo- or copolymer of cyanoethylated acrylate monomers and (3) homo- or copolymer of vinylidene fluoride (fluorine rubber of a vinylidene fluoride type).
However, the above cyanoethylated products (1) have high hygroscopicity and the life of the EL element of an organic dispersion type (hereinafter, just referred to as “EL element”) is short (reduction of luminance upon luminescence and of luminescent efficiency) whereby, in the manufacture of EL elements, an antihygroscopic countermeasure and a tightly closed sealing of the EL element itself by a non-permeable transparent material are necessary. However, even that is not satisfactory for the life extension whereupon they are entirely unable to be used for EL elements of the so-called packageless type having no tightly closed seal. In the case of the polymer of (2), hygroscopicity is improved as compared with the cyanoethylated products of (1) and, in the EL elements where a tightly closed seal is applied, an effect of improving the life is noted but, in the EL elements of a packageless type, that is still unsatisfactory for practical use. In the case of the fluorine rubber of a vinylidene fluoride type (3), it is less hygroscopic and is used especially for EL elements of a packageless type but there is a serious disadvantage that the dielectric constant is insufficient and a sufficient luminance is hardly available.
The present invention is to solve the above-mentioned problems in the prior art and an object of the present invention is to provide a highly dielectric polymer having both low hygroscopicity and high dielectric property and having electric characteristics required for organic electronic materials and also to provide a saccharide-derived monomer which gives the said polymer.
SUMMARY OF THE INVENTION
The present inventors have carried out an intensive study for polymers having a high dielectric constant and an excellent resistance to hygroscopicity and have found that a polymer having the characteristics of a high dielectric constant and a low hygroscopicity is obtained when a monomer where polymerizable functional group is introduced into hydroxyl group or other functional group contained in a saccharide or a saccharide-derived compound while cyanoethyl group is introduced into all of or a part of the remaining hydroxyl group or other functional group is prepared followed by polymerizing the said monomer whereupon the present invention has been accomplished.
Thus, the above-mentioned object of the present invention can be appropriately achieved by a saccharide-derived monomer in which polymerizable functional group is introduced into hydroxyl group or other functional group contained in a saccharide or a saccharide-derived compound while cyanoethyl group is introduced into all of or a part, of residual hydroxyl group or other functional group and also by a highly dielectric polymer prepared by polymerization of the said monomer.
The said saccharide-derived monomer can be manufactured by a method where cyanoethyl group is introduced into all of or a part of hydroxyl group or other functional group contained in a saccharide or a saccharide-derived compound having polymerizable functional group or by a method where a part of hydroxyl group or other functional group contained in a saccharide or a saccharide-derived compound is protected by a protecting group, then cyanoethyl group is introduced into all of or a part of the residual hydroxyl group or other functional group and, after that, deprotection is carried out and then polymerizable functional group is introduced into the said deprotected hydroxyl group or other functional group whereby the present invention can be achieved.
Further, the object of the present invention can be appropriately achieved by the above-mentioned saccharide-derived monomers in which the polymerizable functional group is an ethylenic unsaturated group and the saccharide or the saccharide-derived compound contains a structure of a cyclic pyranose type or a cyclic furanose type. Now, the present invention will be illustrated in detail as hereunder.
DESCRIPTION OF THE PREFERRED EMBODIMENTS
There is no particular limitation for the saccharide and the saccharide-derived compound of the present invention but natural or synthetic ones may be appropriately selected and used depending upon the required characteristics. Thus, examples of the monosaccharide are trioses such as glycerol aldehyde and dihydroxyacetone; tetroses such as erythrose, erythrofuranose, treose, treofuranose and erythrulose; pentoses such as aldopentose, ketopentose, aldepentopyranose, aldopentofuranose and ketopentofuranose; aldopentoses such as arabopyranose, arabofuranose, xylopyranose, xylofuranose, ribofuranose, ribopyranose, lyxopyranose and lyxofuranose; ketopentoses such as ribulose, ribulofuranose, xylulose and xylulofuranose; hexoses such as aldehexose, aldehexopyranose, alfohexofuranose, ketohexose, ketohexopyranose and ketohexofuranose; alkohexoses such as glucose, glucopyranose, glucofuranose, galactose, galactopyranose, mannose, mannopyranose, talose and talopyranose; hetohexoses such as fructose, fructofuranose, fructopyranose, sorbose, sorbopyranose, tagatose, tagatopyranose, psicose and psicopyranose; aldoheptoses such as glycero-galacto-heptose, glycero-galacto-heptopyranose, glycero-manno-heptose, glycero-manno-heptopyranose, glycero-gluco-heptose and glycero-gluco-heptopyranose; ketoheptoses or heptuloses such as altro-heptulose, altro-hetulopyranose, anhydro-altro-heptulopyranose, manno-heptulose, manno-heptulopyranose, talo-heptulose, talo-heptulopyranose, allo-heptulose, allo-heptulopyranose, altro-heptulose and altro-heptulopyranose; ketooctoses or octuloses such as glycero-manno-octulose, glycero-manno-octulopyranose, glycero-galacto-octulose and glycero-galacto-octulopryanose; ketononoses or nonuloses such as erythro-gluco-nonulose, erythro-gluco-nonulopyranose, erythro-galacto-nonulose and erythro-galacto-nonulopyranose; deoxy sugars; dideoxy sugars; amino sugars; sulfur sugars; branched sugars; acidic sugars; sugar alcohols; sugar esters; sugar ethers; and glycosides such as O-glycoside, N-glycoside and C-glycoside.
Examples of natural oligosaccharides and synthetic oligosaccharides are maltoligosaccharide, celloligosaccharide, isomaltoligosaccharide, gentioligosaccharide, nigeroligosaccharide, laminarioligosaccharide, glucan oligomer, sophoroligosaccharide, chitoligosaccharide, N-acetylchitoligosaccharide, lactoligosaccharide, mellioligosaccharide, inuloligosaccharide, fructan, xylan and mannan. Still more examples are the above-mentioned saccharide compounds and saccharide derivatives where those compo

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