Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – At least one aryl ring which is part of a fused or bridged...
Reexamination Certificate
2001-10-31
2003-12-16
Wu, David W. (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
At least one aryl ring which is part of a fused or bridged...
C524S080000, C524S081000, C524S832000, C525S301000
Reexamination Certificate
active
06664324
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a resin solution composition which comprises an acid-modified butene-1/&agr;-olefin copolymer and which is suitable for paint or adhesive applications.
BACKGROUND OF THE INVENTION
Crystalline polybutene-1, which has excellent tensile characteristics, etc., is traditionally used as a material for pipes and films. However, being sparingly soluble in organic solvents, crystalline polybutene-1 is not readily usable for paint or adhesive applications except by means of powder coating.
In the meantime, with regard to a coating-forming agent usable as a component of solution-type paints, adhesives or the like, a modified polybutene-1 has been developed to take advantage of the characteristics of crystalline polybutene-1 and to ensure remarkable coating properties. To give an example, Japanese Patent publication No. Hei 4-27245 proposes a modified polybutene-1 obtained by graft-modifying polybutene-1 with an unsaturated carboxylic acid or an anhydride thereof.
Nevertheless, a solution composition of this modified polybutene-1 lacks storage stability. When stored at 25° C., the solution composition gelates in as short as 10 days, only to degrade the solution fluidity. For this reason, such a composition is not suitable for use as paints, adhesives or the like, where a coating should be formed in a uniform thickness.
Further, in paint or adhesive applications, this modified polybutene-1, which has a high melting temperature, cannot ensure satisfactory coating properties (e.g. adhesion property, water resistance, gasohol resistance) after low-temperature baking or heat sealing is practiced at 100° C. or lower.
Hence, taking advantage of superior characteristics of a modified polybutene-1, the present invention intends to provide a resin solution composition suitable for paint or adhesive applications, which composition can show good storage stability and form a coating with remarkable properties as a paint or adhesive, with the resin having a low melting temperature.
SUMMARY OF THE INVENTION
In order to achieve the above object, the inventors of the present invention have made intensive researches and completed the present invention.
To be specific, the present invention relates to a resin solution composition for paints or adhesives which comprises an acid-modified butene-1/&agr;-olefin copolymer obtained by modifying a butene-1/&agr;-olefin copolymer with an unsaturated carboxylic acid or an acid anhydride thereof. The butene-1/&agr;-olefin copolymer comprises 65 to 85 mol % butene-1 component and 15 to 35 mol % &agr;-olefin component as polymerizable components, the &agr;-olefin component having 2 to 8 carbon atoms and being other than butene-1 component. The acid-modified butene-1/&agr;-olefin copolymer comprises the unsaturated carboxylic acid or the acid anhydride thereof in a proportion of 0.5 to 5% by weight, and wherein the acid-modified butene-1/&agr;-olefin copolymer is dissolved in an organic solvent, in a solid content of 10 to 30% by weight.
In an embodiment of the present invention, the acid-modified butene-1/&agr;-olefin copolymer may have a weight average molecular weight (Mw) in the range of 50,000 to 200,000.
In another embodiment of the present invention, the acid-modified butene-1/&agr;-olefin co-polymer may have a melting temperature in the range of 70° C. to 100° C.
In still another embodiment of the present invention, the organic solvent may comprise an alicyclic hydrocarbon having 5 to 8 carbon atoms in a proportion of 10 to 90% by weight.
In yet another embodiment of the present invention, the organic solvent may comprise an aromatic hydrocarbon in a proportion of 10 to 90% by weight.
In further another embodiment of the present invention, the resin solution composition may further comprise, as a curing agent, a compound having two or more epoxy groups per molecule.
DETAILED DESCRIPTION OF THE INVENTION
A butene-1/&agr;-olefin copolymer used in the present invention comprises, as polymerizable components, 65 to 85 mol % butene-1 component, and 15 to 35 mol % C
2
-C
8
&agr;-olefin component other than butene-1 component.
As the C
2
-C
8
&agr;-olefin component other than butene-1 component, there may be mentioned ethylene, propylene, hexene-1, heptene-1, octene-1, 4-methylpentene-1 and the like, which may be used alone or in combination. Specific examples of the butene -1/&agr;-olefin copolymer include, for example, butene-1/ethylene copolymer, butene-1/propylene copolymer, butene-1/ethylene/propylene terpolymer and butene-1/ethylene/octene-1 terpolymer. Of the above-mentioned &agr;-olefin components, ethylene, propylene and octene-1 are suitable because of the versatility of copolymers.
The content of butene-1 is in the range of 65 to 85 mol %, preferably 70 to 80 mol %. The content of the &agr;-olefin component ranges from 15 to 35 mol %, preferably from 20 to 30 mol %. Where the butene-1 content is less than 65 mol % (where the content of the &agr;-olefin component exceeds 35 mol %), the final acid-modified butene-1/&agr;-olefin copolymer has a low mechanical strength and a weak cohesive force. As a result, the coating shows an inferior adhesion property to polyolefins. On the other hand, where the butene-1 content is over 85 mol % (where the content of the &agr;-olefin component is less than 15 mol %), the final acid-modified butene-1/&agr;-olefin copolymer has a melting temperature of 100° C. or higher. In this case, the coating shows a poor adhesion property after low-temperature baking or heat sealing is practiced at 100° C. or lower in paint or adhesive applications. Besides, depending on the molecular weight, the final acid-modified butene-1/&agr;-olefin copolymer shows an insufficient solubility in an organic solvent and, hence, a poor storage stability. It should be noted that the melting temperature of a polybutene-1 homopolymer is in the range of 122 to 130° C., whereas that of a polybutene-1 homopolymer modified with an unsaturated carboxylic acid or its anhydride ranges from 110 to 125° C.
This butene-1/&agr;-olefin copolymer can be modified with an unsaturated carboxylic acid or an anhydride thereof to give an acid-modified butene-1/&agr;-olefin copolymer.
The unsaturated carboxylic acid or its anhydride used herein includes unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, itaconic acid and citraconic acid; unsaturated carboxylic anhydrides such as maleic anhydride, itaconic anhydride, citraconic anhydride and endomethylenetetrahydrophthalic anhydride. They may be used alone or in combination. Considering the adhesion property of the coating and the price, maleic anhydride is particularly suitable.
This acid-modified butene-1/&agr;-olefin copolymer contains the unsaturated carboxylic acid or its anhydride in a proportion of 0.5 to 5% by weight, preferably 1 to 4% by weight. If the proportion of the unsaturated carboxylic acid or its anhydride is below 0.5% by weight, the acid-modified butene-1/&agr;-olefin copolymer not only shows a poor solubility in an organic solvent but also limits the adhesion property of the coating. Conversely, where the proportion of the unsaturated carboxylic acid or its anhydride exceeds 5% by weight, the coating properties are unsatisfactory. In particular, increase of polarity degrades the water resistance.
The butene-1/&agr;-olefin copolymer is modified with the unsaturated carboxylic acid or its anhydride in a known manner. In a typical reaction, the butene-1/&agr;-olefin copolymer is allowed to react with the unsaturated carboxylic acid or its anhydride in the presence or absence of a solvent (e.g. toluene, xylene) with or without addition of a radical initiator (e.g. benzoyl peroxide, dicumyl peroxide, di-tert-butyl peroxide, lauroyl peroxide, cumene hydroxyperoxide, 2,2′-azobis(isobutyronitrile)). This reaction is carried out under heating at as high as 70 to 250° C.
Preferably, the resulting acid-modified butene-1/&agr;-olefin copolymer has a weight average molecular weight (Mw) ranging from 50,000 to 200,000, particu
Isomoto Kenichiro
Maekawa Shoji
Masuda Takafumi
Toyo Kasei Kogyo Company Limited
Wu David W.
Wu Henry S.
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