Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
2001-05-07
2003-02-18
Cain, Edward J. (Department: 1714)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C524S439000, C524S440000, C524S441000
Reexamination Certificate
active
06521677
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to radiation-curable metal particles comprising a radiation-curable group linked by a silyl group to a metal and, to a liquid curable resin composition comprising a poly-functional (meth)acrylic compound and these metal oxide particles. More particularly, the present invention relates to a liquid curable resin composition which can produce cured products with a high refractive index by application to fabricated plastic articles or films and can also produce anti-reflection films.
BACKGROUND OF INVENTION
Conventionally, a hard coat treatment has been applied as means for protecting surfaces of fabricated plastic materials such as plastic optical parts, touch panels, and film-type liquid crystal elements, as well as coated surfaces such as floors and walls inside buildings. UV curable acrylic-type hard coat materials such as polyester acrylate, urethane acrylate, and epoxy acrylate have been used as such hard coat materials. When used alone, however, these hard coat materials could not sufficiently improve mar resistance, slip characteristics, and stain resistance of the above-mentioned plastic surfaces and coated surfaces.
A method of adding inorganic fillers such as silica or organic fillers such as polyethylene powder and polycarbonate powder and a method of adding additives such as silicone are well known as the method for improving mar resistance, slip characteristics, and stain resistance of fabricated plastic surfaces.
However, the method of adding inorganic or organic fillers has drawbacks such as an increased haze value and impaired appearance of resulting coating films. The method of adding silicone can improve slip characteristics of coating surfaces, but not mar resistance due to abrasive wheels. In addition, a hard coat applied to a touch panel or the like requires an after-treatment step with alkali etching. This may involve hydrolysis of commonly used silicone additives with alkali, resulting in impaired appearance of coatings or peeling of coatings from fabricated plastic materials.
With regard to a thermosetting resin material with a high refractive index, Japanese Patent Pubication No. 12489/1990 discloses a high refractive index resin used for lenses. The resin comprises a polymer obtained by the reaction of a vinyl compound and an urethanized (meth)acrylic monomer which is obtained by the reaction of a (meth)acrylic monomer having a halogen substituted aromatic ring and a polyfunctional isocyanate compound. Although the resin has a high refractive index, its abrasion resistance is insufficient.
On the other hand, with regard to a photopolymerizable cross-linking coating materials, Japanese Patent Application Laid-open No. 169833/1987 discloses a photocurable monomer comprising polyacrylate of dipentaerythritol. Coatings with sufficient hardness can be obtained in a short period of time using this monomer. However, because the coatings have a refractive index of 1.55 or less, the monomer may produce interference stripes if coated over the substrate with a high refractive index such as polycarbonate, polyester carbonate, polyethylene terephthalate, or poly-1,4-cyclohexane dimethylane terephthalate. Thus, this material is inadequate for use with optical products requiring high resolution.
PROBLEMS TO BE SOLVED BY THE INVENTION
An object of the present invention is to provide a liquid curable resin composition which can produce transparent cured products with a high refractive index, high hardness, and superior abrasion resistance, and can be suitably used as a coating material.
Another object of the present invention is to provide a liquid curable resin composition suitable for producing a hard coat over the surface of fabricated plastic materials.
Other objects and features of the present invention will become apparent from the following detailed description of the present invention.
SUMMARY OF THE INVENTION
The present invention provides radiation-curable metal particles comprising a radiation-curable group linked by a silyl group to a metal, in particular where said metal is not inclusive of silicon metal Also provided are methods to prepare such particles.
In addition, the present invention provides compositions that comprise the above-noted particles. Preferred compositions provided by the present invention are compositions that, after radiation cure, provide products of high transparency, low haze, and a refractive index of more than 1.55.
Furthermore, the present invention provides articles made by curing the above compositions, including articles comprising coatings and films formed from such compositions. In particular articles having antireflection properties are provided.
DETAILED DESCRIPTION OF THE INVENTION
Herein certain terms are used to define certain chemical aspects. These terms are defined below.
A (meth)acrylic compound is a compound comprising a (meth)acryloyl group, whereby it is noted that a (meth)acrylol group, by definition, comprises an unsaturated bond.
When reference is made to groups in the periodic table of elements, reference is made to the periodic table appearing on the inside front cover of “CRC Handbook of Chemistry and Physics”, 78th ed. 1997-1998, and to the “New Notation” noted thereon.
Consequently, the groups are numbered in arabic notation, for example group 11 is the group consisting of copper, silver and gold, group 2 is the group that includes magnesium, calcium and barium etc. Furthermore, in this application, group 3 is considered to include elements 57-71 and elements 89-103, i.e. the lanthanides and actinides.
The present invention provides a radiation-curable metal particle comprising a radiation-curable group linked by a silyl group to a metal, which hereinafter will also be referred to as “component B”. It will be appreciated by one of ordinary skill in the art that “component B” may refer to a single particle, multiple particles, or a mixture of particles.
The present invention further provides compositions comprising these particles. Such radiation-curable compositions may be any suitable radiation-curable composition, and may further comprise a (meth)acrylic compound (hereinafter also referred to as “component (A)”). The composition may, independent of the presence of component (A), also comprise a radiation polymerization initiator (hereinafter also referred to as “component (C)”).
Component (A) can be any suitable (meth)acrylic compound. Preferably, component(A) comprises at least three (meth)acryloyl groups in the molecule, more preferably from 3 to 10 (meth)acryloyl groups, even more preferably from 4 to 10 (meth)acryloyl groups, and most preferably from 4 to 8 (meth)acryloyl groups.
Given as examples of such a (meth)acrylic compound are trimethylolpropane tri(meth)acrylate, trimethylolpropane trioxyethyl (meth)acrylate, tris(2-hydroxyethyl)isocyanurate tri(meth)acrylate, pentaerythritol tri(meth)acrylate, pentaerythritol tetra(meth)acrylate, dipentaerythritol hexa(meth)acrylate, and the like.
As examples of commercially available products of the (meth)acrylic compound having at least three (meth)acryloyl groups in the molecule, Kayarad DPHA, DPCA-20, DPCA-30, DPCA-60, DPCA-1 20, D-310, D-330, PET-30, GPO-303, TMPTA, THE-330, TPA-330 (manufactured by Nippon Kayaku Co., Ltd.), Aronix M-315, M-325 (manufactured by Toagosei Co., Ltd.), and the like can be given.
The proportion of the (meth)acrylic compound having at least three (meth)acryloyl groups in the molecule used as the component (A) in the composition of the present invention is in the range preferably from 1 to 99 wt %, more preferably from 10 to 90 wt %, and particularly preferably from 30 to 70 wt %. The number of (meth)acryloyl groups in the molecule is preferably from 4 to 10, and more preferably from 4 to 8.
The particles of component (B) comprise a radiation-curable group linked by a silyl group to a metal. The metal can be any suitable metal, and is preferably a metal selected from the metals listed in groups 2-16 from the periodic table of elements exclusive of silicon metal. Preferably t
Eriyama Yuichi
Nishikawi Isao
Ukachi Takashi
Yashiro Takao
Cain Edward J.
DSM N.V.
Pillsbury & Winthrop LLP
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