Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
1998-12-03
2001-07-24
Lipman, Bernard (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
Reexamination Certificate
active
06265508
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to a metal surface treatment agent which is used for applying in advance a metal surface as an adherend in adhering a macromolecular material to a metal by using an adhesive.
BACKGROUND OF THE INVENTION
In adhesion of a macromolecular material to a metal, as compared with the adhesion to a base metal such as cobalt, chromium, nickel, titanium, iron, and copper, or an alloy thereof, the adhesion to a chemically stable noble metal such as gold, platinum, and palladium, or a noble metal alloy containing such a noble metal as a major component is extremely difficult, and hence, the present situation is that any thoroughly satisfactory adhesion technologies have not yet been established.
As attempts for improving the adhesive properties to a noble metal, there have been proposed some methods for applying a primer onto a metal surface as an adherend, a method for sandblasting to physically roughing a metal surface as an adherend, a method for plating a metal surface as an adherend with tin, a method for subjecting a metal surface as an adherend to oxidation processing, and the like.
Of these methods, the method for applying a primer onto a metal surface as an adherend is simplest, and examples of such method include a method in which 6-(4-vinylbenzyl-n-propyl)amino-1,3,5-triazine-2,4-dithione (hereinafter referred to as “VBATDT”) is used as a primer to be applied, as disclosed in Japanese Patent Laid-Open No. 64-83254, and method in which a polymerizable monomer containing a thiophosphoric acid group therein is used as a primer to be applied, as disclosed in Japanese Patent Laid-Open No. 1-138282 and Japanese Patent Laid-Open No. 3-310122.
Although many of the above-described conventional technologies are admitted to have an effect for increasing the adhesive strength under dry conditions, they involve such a defect that the water resistance or durability is poor.
Of the methods for applying a primer onto a metal surface as an adherend, the method of using VBATDT can not be said to be sufficient in an effect for improving the adhesive properties to any of base metals or noble metals; and while the method of using a monomer containing a thiophosphoric acid group therein is admitted to have an effect for improving the adhesive properties, this method not only has a problem in storage or handling of the primer, because the substance itself is unstable, but also involves such a problem that the water resistance or durability is inferior.
SUMMARY OF THE INVENTION
Thus, an object of the present invention is to provide a metal surface treatment agent which can impart a high adhesive strength with superior durability to various metals including base metals to noble metals in adhesion of a macromolecular material to a metal by extremely simple processing and is good in storage stability.
In order to achieve the above-described object, the present inventor made extensive and intensive investigations. As a result, while paying attention to a polymerizable monomer containing a phosphoric acid ester group therein which is inferior in adhesive properties to noble metals but superior in adhesive properties to base metals, a polymerizable monomer was combined with a polymerizable monomer containing a thiophenecarboxylic acid ester group therein which is superior in adhesive properties to a noble metal. As a result, a success was achieved in making a metal surface treatment agent which is superior in adhesive properties to various metals including base metals to noble metals, has superior adhesive properties to various metals and superior durability by synergistic effects thereof, as compared with the case in which an individual monomer is used, is good in storage stability, and is easy for handling, leading to accomplishment of the present invention.
That is, the present invention is to provide a metal surface treatment agent comprising from 0.001 to 10% by weight of a polymerizable monomer containing a thiophenecarboxylic acid ester group therein and from 0.001 to 10% by weight of a polymerizable monomer containing a phosphoric acid ester group therein dissolved in an organic solvent.
DETAILED DESCRIPTION OF THE INVENTION
As the polymerizable monomer containing the thiophenecarboxylic acid ester group therein, compounds represented by the following chemical formulae can be used:
wherein R
1
is H or CH
3
; R
2
is H, Cl, COOH, COCl, CONH
2
, or CN; and n is an integer of 2 to 16.
Specific examples include 2-thiophenecarboxylic acid-2-(meth)acryloyloxyethyl ester, 2,5-thiophenedicarboxylic acid hydrogen-2-(meth)acryloyloxyethyl ester, 2,5-thiophenedicarboxylic acid di(2-(meth)acryloyloxyethyl) ester, 2-thiophenecarboxylic acid-4-(meth)acryloyloxybutyl ester, 2,5-thiophenedicarboxylic acid hydrogen-4-(meth)acryloyloxybutyl ester, 2,5-thiophenedicarboxylic acid di(4-(meth)acryloyloxybutyl) ester, 2-thiophenecarboxylic acid-6-(meth)acryloyloxyhexyl ester, 2,5-thiophenedicarboxylic acid hydrogen-6-(meth)acryloyloxyhexyl ester, 2,5-thiophenedicarboxylic acid di(2-(meth)acryloyloxyhexyl) ester, 2-thiophenecarboxylic acid-8-(meth)acryloyloxyoctyl ester, 2,5-thiophenedicarboxylic acid hydrogen-8-(meth)acryloyloxyoctyl ester, 2,5-thiophenedicarboxylic acid-di(8-(meth)acryloyloxyoctyl)ester, 2-thiophenecarboxylic acid-10-(meth)acryloyloxydecyl ester, 2,5-thiophenedicarboxylic acid hydrogen-10-(meth)acryloyloxydecyl ester, 2,5-thiophenedicarboxylic acid-di(10-(meth)acryloyloxydecyl) ester, 2-thiophenecarboxylic acid-12-(meth)acryloyloxydodecyl ester, 2,5-thiophenedicarboxylic acid hydrogen-12-(meth)acryloyloxydodecyl ester, 2,5-thiophenedicarboxylic acid-di(12-(meth)acryloyloxydodecyl) ester, 2-thiophenecarboxylic acid-14-(meth)acryloyloxytetradecyl ester, 2,5-thiophenedicarboxylic acid hydrogen-14-(meth)acryloyloxytetradecyl ester, 2,5-thiophenedicarboxylic acid-di(14-(meth)acryloyloxytetradecyl) ester, 2-thiophenecarboxylic acid-16-(meth)acryloyloxyhexadecyl ester, 2,5-thiophenedicarboxylic acid hydrogen-16-(meth)acryloyloxyhexadecyl ester, and 2,5-thiophenedicarboxylic acid-di(16-(meth)acryloyloxyhexadecyl) ester.
Of these compounds are particularly preferred 2-thiophenecarboxylic acid-2-(meth)acryloyloxyethyl ester, 2,5-thiophenedicarboxylic acid hydrogen-2-(meth)acryloyloxyethyl ester, 2,5-thiophenedicarboxylic acid di(2-(meth)acryloyloxyethyl) ester, 2-thiophenecarboxylic acid-10-(meth)acryloyloxydecyl ester, 2,5-thiophenedicarboxylic acid hydrogen-10-(meth)acryloyloxydecyl ester, and 2,5-thiophenedicarboxylic acid-di(10-(meth)acryloyloxydecyl) ester because their raw materials are readily available and do not require complicated synthesis methods.
In addition, as the polymerizable monomer containing the phosphoric acid ester group therein, compounds represented by the following chemical formula can be used:
wherein R
1
is H or CH
3
;
and n is an integer of 2 to 16.
Specific examples include 2-(meth)acryloyloxyethyl phosphate, 4-(meth)acryloyloxybutyl phosphate, 6-(meth)acryloyloxyhexyl phosphate, 8-(meth)acryloyloxyoctyl phosphate, 10-(meth)acryloyloxydecyl phosphate, 12-(meth)acryloyloxydodecyl phosphate, 14-(meth)acryloyloxytetradecyl phosphate, and 16-(meth)acryloyloxyhexadecyl phosphate.
Of these compounds are particularly preferred 2-(meth)acryloyloxyethyl phosphate and 10-(meth)acryloyloxydecyl phosphate because their raw materials are readily available and do not require complicated synthesis methods.
Examples of the organic solvent which dissolves therein the polymerizable monomer containing the thiophenecarboxylic acid ester group therein and the polymerizable monomer containing the phosphoric acid ester group include acetone, methyl ethyl ketone, tetrahydrofuran, dioxane, ethyl acetate, methyl methacrylate, chloroform, dichloromethane, benzene, and toluene. These compounds can be used singly or in admixture of two or more thereof.
A suitable concentration of the polymerizable monomer containing the thiophenecarboxylic acid ester group therein and a suitable concentration of the polymerizable monomer containing the phosphoric acid ester
GC Corporation
Lipman Bernard
Oblon, Spivak, McCelland, Maier & Neustadt, P.C.
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