Hydrolyzable resin containing aldehyde bounded thereto and self-

Details Hydrolyzable resin containing aldehyde bounded thereto and self- Hydrolyzable resin containing aldehyde bounded thereto and self-

1998-03-09

1999-06-22

Yoon, Tae

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

523122, 5253287, 526315, C09J20102, C08F 1638

Patent

active

059143576

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 aldehyde compounds such as benzaldehyde 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 aldehyde in a controlled manner while the remaining hydrolyzed resin is gradually consumed by dissolving in water.


DISCLOSURE OF THE INVENTION

It is well-known in the organic chemistry that an primary amine reacts with an aldehyde to form a Schiff base. The present invention utilizes this reaction to bind the aldehyde to the vehicle resin in a hydrolyzable form.
According to the present invention, there is provided a vehicle resin for use in antifouling paints comprising a vinyl polymer having a plurality of primary amino groups in the form of a Schiff base in the molecule. The resin having a plurality of primary amino groups in the form of a Schiff base may be produced by reacting an aldehyde with the corresponding vinyl polymer having a plurality of primary amino groups. Alternatively, the vinyl polymer Schiff base may be produced by reacting a primary amine monomer with an aldehyde and then copolymering the resulting monomer with other comonomers.


DESCRIPTION OF THE PREFERRED EMBODIMENTS

The first method for producing the vinyl polymer having a plurality of primary amino groups in the form of a Schiff base in the molecule comprises reacting an aldehyde with the corresponding vinyl polymer having primary amino groups. The vinyl polymer having primary amino groups may be produced, in turn, by copolymerizing a primary amine monomer-acid addition salt such as allylamine hydrochloride or 2-aminoethyl (meth)acrylate hydrochloride with other comonomers and then treating the resulting polymer with an alkali to regenerate the primary amine function. We have found that when using aminostyrenes (o-, m- and p-) as the primary amine monomer, the primary amino group-containing vinyl polymer can be directly produced by the copolymerization method.
The above-mentioned primary amine monomers are examples of those monomers producing a vinyl polymer having the primary amino group at the end of pendant groups thereof. Polymers having primary amino groups which are directly attached to the polymer backbone chain, i.e. polymers comprising a number of recurring units corresponding to vinylamine which does not occur as an isolated monomer may also be produced by using N-vinylacrylamide as a starting monomer. Since the acrylolyl double bond is relatively less reactive than the vinyl double bond, this monomer acts as a monofunctional monomer under certain conditions to produce vinyl po

REFERENCES:
patent: 3177171 (1965-04-01), Gruber et al.
patent: 4178430 (1979-12-01), Bilow

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