Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1999-08-24
2001-03-13
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...
C523S177000, C524S430000, C524S431000, C524S432000, C524S556000, C524S558000
Reexamination Certificate
active
06201040
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates generally to an antifouling coating composition which can control the dissolution rate of a coating film and which can exert antifouling properties for a long period of time.
2. Description of Related Art
Heretofore, a resin having a carboxylate of tin has been used as a binder for an antifouling coating composition. However, since such resins can be harmful, the replacement of the tin carboxylate resin with another resin has been required in some instances. Thus, various resins, mainly having carboxylates of copper and zinc, have been investigated. For example, some typical alternative resins have been suggested in Japanese Patent Application Laid-Open Nos. 57464/1987 and 209005/1996, both of which are incorporated herein by reference in their entirety.
However, it is difficult to obtain sufficient control the erosion rate of a coating film obtained from each of these resins, and furthermore, while such resins can exert antifouling properties to some extent, a problem can arise that the antifouling properties cannot be maintained over an extended time period.
SUMMARY OF THE INVENTION
An object of the present invention is to provide an antifouling coating composition which permits control of the dissolution rate of a coating film and which can exert antifouling properties for a long period of time.
The present invention is directed to an antifouling coating composition comprising an antifouling resin (A) obtained by reacting a base resin including, in one molecule, a carboxyl group and a group having a polyalkylene glycol structure of the following formula (1)
(C
m
H
2m
O)
n
R
1
(1)
wherein R
1
is hydrogen, or a straight-chain, branched or cyclic alkyl group or aralkyl group having 1 to 20 carbon atoms, m is an integer of 1 to 4, and n is an integer of 1 to 100, with an oxide or a hydroxide of a metallic atom that is at least divalent in the presence of water, the water being included in an amount of 1 to 30% by weight based on the weight of the solids of the base resin, and an antifouling agent (B).
Additional advantages, features and modifications will readily occur to those skilled in the art. Therefore, the invention in its broader aspects is not limited to the specific details, and representative devices, shown and described herein. Accordingly, various modifications may be made without departing from the spirit or scope of the general inventive concept as defined by the appended claims and their equivalents.
DETAILED DESCRIPTION OF A PREFERRED EMBODIMENT
In the present invention, an antifouling resin (A) can be obtained by reacting a base resin including, in one molecule, a carboxyl group and a group having a polyalkylene glycol structure represented by the above-mentioned general formula (1) with an oxide or a hydroxide of a metallic atom that is at least divalent in the presence of water in an amount of 1 to 30% by weight based on the weight of the solids of the base resin.
The above-mentioned base resin possesses the group having the polyalkylene glycol structure represented by the above-mentioned general formula (1), which improves self-polishing property without impairing the physical properties of the coating composition. In the above-mentioned general formula (1), m is in integer of 1 to 4, and n is an integer of 1 to 100, respectively. If m is in excess of 4 or if n is in excess of 100, the improvement effect of the self-polishing property may not be as dramatic or noticeable.
Examples of the above-mentioned base resin include one or more of polyester resins, polyurethane resins and polyamide resins. A particularly suitable base resin is an acrylic polymer obtained by copolymerizing a carboxyl group-containing monomer and another monomer copolymerizable therewith, or by copolymerizing a carboxyl group-containing monomer, a monomer having a group with a polyalkylene glycol structure and another monomer copolymerizable therewith in the presence of a radical polymerization initiator in accordance with any customer's method, such as by employing solution polymerization.
Examples of the above-mentioned carboxyl group containing monomer include one or more of (meth)acrylic acid, crotonic acid, itaconic acid, maleic acid and fumaric acid.
Examples of the above-mentioned monomer having the group with the polyalkylene glycol structure include one or more of methoxyethyl (meth)acrylate, hydroxyethyl (meth)acrylate, methoxypolyethylene glycol (meth) acrylate, nonylphenoxpolyethylene glycol (meth)acrylate and methoxypolyethylene glycol (meth) acrylate.
Examples of the above-mentioned other monomer copolymerizable therewith include one or more of vinyl aromatic compounds such as styrene, Q-methylstyrene, vinyltoluene and achlorostyrene; alkyl esters and cycloalkyl esters having 1 to 24 carbon atoms of acrylic acid and methacrylic acid such as methyl (meth)acrylate, ethyl (meth)acrylate, n-propyl (meth)acrylate, iso-propyl (meth)acrylate, (n-, iso- and tert- )butyl (meth)acrylate, hexyl (meth)acrylate, cyclohexyl (meth)acrylate, 2-ethylhexyl (meth)acrylate, n-octyl (meth)acrylate, decyl (meth)acrylate, lauryl (meth)acrylate, stearyl (meth)acrylate, isobornyl (meth)acrylate; perfluoroalkyl (meth)acrylates such as perfluorobutylethyl (meth) acrylate, perfluoroisononylethyl (meth) acrylate and perfluorooctylethyl (meth)acrylate; and fluoroolefins. In addition, a so-called macromonomer which is a polymer of one or more monomers thereof and which has a polymerizable unsaturated group at one terminal end can also be mentioned as a suitable polymerizable monomer.
Examples of the solvent which can be used in the solution polymerization of the above-mentioned monomer mixture include one or more of alkylbenzene derivatives such as benzene, toluene and xylene; acetate solvents such as ethyl acetate, propyl acetate, butyl acetate, amyl acetate, methoxybutyl acetate, methyl acetoacetate, ethyl acetoacetate, methyl CELLOSOLVE ACETATE, CELLOSOLVE ACETATE, diethylene glycol acetate monomethyl ether and CARBITOL ACETATE; ether solvents such as dioxane, ethylene glycol diethyl ether, ethylene glycol dibutyl ether and diethylene glycol diethyl ether; alcoholic solvents such as methanol, ethanol, propanol, isopropanol and (n-, iso- and tert-)butanols; and ketone solvents such as acetone, methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone. They can be used singly or in the form of a mixture of two or more thereof.
Examples of the radical polymerization initiator include one or more of peroxides such as benzoyl peroxide, di-t-butyl hydroperoxide, tert-butyl hydroperoxide, cumyl peroxide, cumene hydroperoxide, diisopropylbenzene hydroperoxide, tertbutyl peroxybenzoate, lauryl peroxide, acetyl peroxide and tert-butylperoxy-2-ethyl hexanoate; and azo compounds such as &agr;,&agr;′-azobisisobutyronitrile, &agr;,&agr;′-azobis-2-methylbutyronitrile, azobisdimethylvaleronitrile and azobiscyclohexanecarbonitrile.
The weight-average molecular weight of the base resin obtained as described above in some embodiments is usually in the range of 1,000 to 200,000, preferably 2,000 to 100,000, more preferably 2,000 to 50,000. If the weight-average molecular weight is less than 1,000, or about 1,000 drying properties may be poor, so that weathering resistance and durability of the coating film deteriorate. On the other hand, if the molecular weight is more than 200,000 or about 200,000, the finished appearance may tend to deteriorate, as well as the coating film may lack sufficient self-polishing and sufficient antifouling properties may be difficult to obtain.
Furthermore, if the above-mentioned base resin includes a group having a polyalkylene glycol structure, in order to optimize the improvement of self-polishing performance, preferably at least 0.005 mol of an alkylene glycol unit is contained in 100 g of the base resin.
In the present invention, the resin (A) can be obtained, for example, by reacting the base resin obtained as described above with an oxide or a hydroxide of an at least
Kawai Hiroyuki
Kitajima Masakazu
Yamashita Hiroshi
Cain Edward J.
Kansai Paint Co. Ltd
Rader Fishman & Grauer
Wyrozebski Katarzyna
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