Compositions: coating or plastic – Coating or plastic compositions – Contains fireproofing or biocidal agent
Patent
1998-03-09
1999-11-16
Green, Anthony
Compositions: coating or plastic
Coating or plastic compositions
Contains fireproofing or biocidal agent
106 1832, 106 1833, 106 1834, 106 1835, 106 1836, 424 7809, 523122, 523177, C09D 514, A01N 2500, A01N 2502
Patent
active
059850124
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND ART
This invention relates to a hydrolyzable resin for use as a vehicle resin of antifouling paints as well as antifouling paints containing said resin.
Antifouling paints containing as a vehicle resin a trialkyltin-containing polymer are known. These resins are advantageous in controlling the release of antifouling agent to a minimum level sufficient to maintain desired antifouling effect at a constant level for a long period of time. In application, the vehicle resin consisting of a trialkyltin-containing polymer is hydrolyzed by the action of weakly alkaline sea water to release the trialkyltin, and at the same time the resin becomes water-soluble so that the paint film is consumed and smoothed. This contributes to the reduction of the frictional resistance of ships against water and, therefore, to the reduction of fuel cost.
The vehicle resins of this type of paints, known as "self-polishing paints", typically consist of copolymers of trialkyltin (meth)acrylate. However, strong concern about the toxic effect of trialkyltin on the ecological system has led to a demand for a new vehicle resin of self-polishing antifouling paints which may replace the trialkyltin-containing polymers.
Most of vehicle resins for self-polishing paints known in the prior art release a metal compound or ion. Recently we have found that some primary amines such as aniline or derivatives thereof exhibit an antifouling activity on a variety of aquatic organisms adhering to ships.
It is, therefore, a principal object of the invention to provide a new type of vehicle resins for use in antifouling paint which release upon hydrolysis an antifouling primary amine in a controlled manner while the remaining hydrolyzed resin is gradually consumed by dissolving in water.
SUMMARY OF THE INVENTION
It is well-known in the organic chemistry that a primary amine reacts with an aldehyde to form a Schiff base and also with a ketone to form a ketimine.
The present invention utilizes these reactions for combining a primary amine to the vehicle resin in a hydrolyzable form.
According to the invention, there is provided a vehicle resin used for antifouling paints comprising a primary amine-bound vinyl polymer which is produced by binding the primary amine to a carbonyl group-containing pendant group possessed by the corresponding vinyl polymer using the above dehydration-condensation reaction. Alternatively the primary amine-bound vinyl polymer may be produced by binding the primary amine to a carbonyl group-containing monomer using the above reaction and then copolymerizing the resulting monomer with other monomers copolymerizable therewith.
The present invention also provides an antifouling paint comprising the above vehicle resin.
In order to produce the primary amine-bound vinyl polymer of the present invention, it is necessary to start from a monomer having an aldehyde or ketone function. Typical examples of aldehyde monomers include acrolein, methacrolein, crotonaldehyde, cinnamaldehyde and 4-vinylbenzaldehyde. It is advantageous for easy handling and for preventing side reactions that such aldehyde monomers as acrolein which is volatile, irritative and unstable be used in the form of a cyclic acetal with ethylene glycol or 1,3-propanediol in the polymerization followed by regenerating the aldehyde function prior to the reaction with the primary amine. Examples of monomers having ketone function include N-(2-acetyl-1,1-dimethylethyl)acrylamide otherwise called diacetoneacrylamide.
The reaction of a primary amine with the aldehyde or ketone group can be performed either prior to or subsequent to the copolymerization of the aldehyde monomer or ketone monomer with other monomers.
Examples of copolymerizable monomers include alkyl (meth)acrylates such as methyl (meth)acrylate, ethyl (meth) acrylate, n-propyl (meth)acrylate, n-butyl (meth)acrylate, t-butyl (meth)acrylate or 2-ethylhexyl (meth)acrylate; and other mnomers such as styrene, .alpha.-methylstyrene, vinyltoluene, (meth)acrylamide, (meth)acrylonitrile, vinyl acetate, vinyl p
REFERENCES:
WPIDS Abstract No. 88-068423, abstract of Japanese Patent Specification No. 63-023906, Feb. 1988.
Nakamura Isao
Yamamori Naoki
Green Anthony
Nippon Paint Co. Ltd.
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