Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Mixing of two or more solid polymers; mixing of solid...
Reexamination Certificate
2001-04-20
2003-04-29
Sellers, Robert E. L. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Mixing of two or more solid polymers; mixing of solid...
C525S122000, C525S330300, C525S330500, C525S330600, C525S333300, C525S333400
Reexamination Certificate
active
06555622
ABSTRACT:
TECHNICAL FIELD
The present invention relates to an epoxy resin composition. More particularly, it relates to an epoxy-terminated vinyl polymer, a composition comprising the polymer and a flexible composition comprising an epoxy resin and a reactive functional group-containing vinyl polymer.
BACKGROUND ART
When combined with a curing agent, epoxy resins give cured products having a three-dimensionally crosslinked structure and thus exhibiting various desirable characteristics. Crosslinked epoxy groups are exploited in a wide range of applications, such as paints, electrics/electronics, civil engineering/building, adhesives, and composite materials, owing to excellence in the balance between heat resistance and mechanical/physical properties and in electrical characteristics adhesive characteristics and corrosion resistance, among others, and to the ease of molding.
On the other hand, epoxy resins are generally hard and brittle by nature and may form cracks upon exposure to stress strain or thermal shock on the occasion of curing or in use, hence epoxy resins are required to be rendered tenacious and flexible. In the field of IC sealing, for instance, where packages are becoming smaller and thinner, improvement in crack resistance is needed.
As a means for providing epoxy resins with flexibility, there maybe mentioned the combined use of a flexible epoxy resin. The flexible epoxy resin includes, among others, diglycidyl esters of long-chain fatty acids such as linoleic acid dimer; polyglycidyl ethers of polyhydric alcohols such as glycerol, pentaerythritol and trimethylolpropane; diglycidyl ethers of polyalkylene glycols such as polyethylene glycol; and the like. However, long-chain fatty acid glycidyl esters are short of alkali resistance and gasoline resistance, although they are excellent in flexibility. Polyalkylene glycol glycidyl ethers also have problems, for example they are inferior in weathering resistance.
It is known that crosslinking functional group-terminated liquid oligomers, when used alone or combined with an appropriate curing agent, give cured products excellent in rubber elasticity. Thus, it is expected that an epoxy-terminated vinyl polymer, if successfully obtained in a simple and easy manner, might serve as a novel flexible epoxy resin excellent in flexibility. Further, vinyl polymers show various characteristics depending on the main chain skeleton thereof and, therefore, are amenable to molecular design according to the use/purpose thereof.
As for the production of epoxy-terminated vinyl polymers, U.S.Pat. No. 4,429,099, for instance, discloses a method which comprises reacting the termini of polyisobutylene with a phenol in the manner of Friedel-Crafts reaction and further utilizing the reactivity of the phenol group to synthesize an epoxy-terminated polyisobutylene. However, low-polarity polymers such as polyisobutylene are poor in compatibility with epoxy resins and, if well dispersed, give a high viscosity.
In view of the above state of the art, it is an object of the present invention to provide a vinyl polymer with an epoxy group terminally introduced therein and an epoxy resin composition in which such polymer is used.
A further object of the invention is to provide an epoxy resin composition having flexibility by adding a vinyl polymer having a terminal reactive functional group to an epoxy resin.
SUMMARY OF THE INVENTION
Thus, according to a first aspect thereof, the invention provides an epoxy resin composition
which comprises a vinyl polymer having a group represented by the following general formula (1) at a main chain terminus
as well as a vinyl polymer having a group represented by the following general formula (1) at a main chain terminus.
In the above formula, R
1
, R
2
and R
3
are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond, and R
1
and R
2
or R
2
and R
3
may be combined together at respective other termini to form a cyclic structure.
In accordance with a second aspect, the invention provides an epoxy resin composition
which comprises (A) an epoxy resin and (B) a vinyl polymer having a main chain produced by living radical polymerization and a reactive functional group at a main chain terminus.
In the following, the present invention is described in detail.
DETAILED DISCLOSURE OF THE INVENTION
The first aspect of the invention lies in an epoxy resin composition comprising a vinyl polymer terminally having a group represented by the general formula (1) shown above, namely an epoxy-terminated vinyl polymer.
In the general formula (1), R
1
, R
2
and R
3
are the same or different and each represents a hydrogen atom, a monovalent hydrocarbon group containing 1 to 10 carbon atoms or a monovalent group containing 1 to 10 carbon atoms as derived from two hydrocarbon groups by being bound together via an ether bond or ester bond, and R
1
and R
2
or R
2
and R
3
may be combined together at respective other termini to form a cyclic structure.
The monomer constituting the main chain of the above vinyl polymer is not particularly restricted but maybe any of various monomers. As examples, there may be mentioned (meth)acrylic monomers such as (meth)acrylic acid, methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, isopropyl (meth)acrylate, n-butyl (meth)acrylate, isobutyl (meth)acrylate, tert-butyl (meth)acrylate, n-pentyl (meth)acrylate, n-hexyl (meth)acrylate, cyclohexyl (meth)acrylate, n-heptyl (meth)acrylate, n-octyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, phenyl (meth)acrylate, toluyl (meth)acrylate, benzyl (meth)acrylate, 2-methoxyethyl (meth)acrylate, 3-methoxybutyl (meth)acrylate, 2-hydroxyethyl (meth)acrylate, 2-hydroxypropyl (meth)acrylate, stearyl (meth)acrylate, glycidyl (meth)acrylate, 2-aminoethyl (meth)acrylate, &ggr;-(methacryloyloxypropyl)trimethoxysilane, (meth)acrylic acid-ethylene oxide adducts, trifluoromethylmethyl (meth)acrylate, 2-trifluoromethylethyl (meth)acrylate, 2-perfluoroethylethyl (meth)acrylate, 2-perfluoroethyl-2-perfluorobutylethyl (meth)acrylate, 2-perfluoroethyl (meth)acrylate, perfluoromethyl (meth)acrylate, diperfluoromethylmethyl (meth)acrylate, 2-perfluoromethyl-2-perfluoroethylmethyl (meth)acrylate, 2-perfluorohexylethyl (meth)acrylate, 2-perfluorodecylethyl (meth)acrylate and 2-perfluorohexadecylethyl (meth)acrylate; styrenic monomers such as styrene, vinyltoluene, &agr;-methylstyrene, chlorostyrene, and styrenesulfonic acid and salts thereof; fluorine-containing vinyl monomers such as perfluoroethylene, perfluoropropylene and vinylidene fluoride; silicon-containing vinyl monomers such as vinyltrimethoxysilane and vinyltriethoxysilane; maleic anhydride, maleic acid and monoalkyl esters and dialkyl esters of maleic acid; fumaric acid and monoalkyl esters and dialkyl esters of fumaric acid; maleimide monomers such as maleimide, methylmaleimide, ethylmaleimide, propylmaleimide, butylmaleimide, hexylmaleimide, octylmaleimide, dodecylmaleimide, stearylmaleimide, phenylmaleimide and cyclohexylmaleimide; nitrile-containing vinyl monomers such as acrylonitrile and methacrylonitrile; amido-containing vinyl monomers such as acrylamide and methacrylamide; vinyl esters such as vinyl acetate, vinyl propionate, vinyl pivalate, vinyl benzoate and vinyl cinnamate; alkenes such as ethylene and propylene; conjugated dienes such as butadiene and isoprene; vinyl chloride, vinylidene chloride, allyl chloride, allyl alcohol and so forth. These may be used singly or a plurality of them may be copolymerized. Preferred among them from the viewpoint of physical properties of products, among others, are styrenic monomers and (meth)acrylic monomers, more preferably (meth)acrylic ester monomers, still more preferably acrylic ester monomers, and butyl acrylate is most preferred. In the practice of the invention, the
Fujita Masayuki
Kitano Kenichi
Nakagawa Yoshiki
Connolly Bove & Lodge & Hutz LLP
Kaneka Corporation
Sellers Robert E. L.
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