Provided are an antifouling film, which includes silica particles (a), a polymer (b) having an acrylamide structure and at least one substituent selected from the group consisting of SO.sub.3M and COOM, and a polymer (c) having an acrylamide structure and a hydrocarbon group having 2 to 20 carbon atoms, and a composition for forming an antifouling film, an antifouling film laminate, and a method for manufacturing an antifouling film which are applications of the antifouling film. M represents a hydrogen atom or represents an atom or an atomic group which can become a cation by being dissociated.

First embodiment of a (meth)acrylic copolymer in the present invention includes following: a (meth)acrylic copolymer having at least one kind of constitutional unit selected from the group consisting of a constitutional unit (A1) having at least one kind of structure (I) selected from the group consisting of structures represented by the following formula (1), formula (2), or formula (3) and a constitutional unit (A2) having a triorganosilyloxycarbonyl group and a constitutional unit (B) derived from a macromonomer (b):

##STR00001## (where, X represents O, S, or NR.sup.14, R.sup.14 represents a hydrogen atom or an alkyl group, R.sup.1 and R.sup.2 each represent a hydrogen atom or an alkyl group having from 1 to 10 carbon atoms, R.sup.3 and R.sup.5 each represent an alkyl group having from 1 to 20 carbon atoms, a cycloalkyl group, or an aryl group, and R.sup.4 and R.sup.6 each represent an alkylene group having from 1 to 10 carbon atoms).

Provided is a silyl polymer-based antifouling coating composition that is capable of forming a coating film in which cracking is inhibited from occurring for a long period from the early stage of immersion in seawater and fresh water and enables to maintain excellent coating film consumption for a long term. The antifouling coating composition includes: a copolymer (A) containing a structural unit (a-1) derived from styrene or the like, a structural unit (a-2) derived from glycidyl (meth)acrylate, and optionally a structural unit (a-3) derived from another ethylenically unsaturated monomer; a polymer (B) containing a structural unit (b-1) derived from a monomer represented by the following Formula (b1): ##STR00001##
wherein X is a hydrogen atom or a carboxyl group; R.sup.1 is a hydrogen atom or a methyl group; R.sup.2 to R.sup.6, which may be the same as or different from each other, are C.sub.1-C.sub.6 straight or branched chain alkyl; and n is an integer of 0 or 1 or more; and an antifoulant.

The present invention relates to an antifouling coating composition, an antifouling coating film, a substrate with an antifouling coating film and a production process for the substrate. The antifouling coating composition includes a hydrolyzable polymer (A) having a structural unit represented by the following formula (1) and having a weight-average molecular weight of 1000 to 5000 and an antifouling agent (B) including (b1) 4-bromo-2-(4-chlorophenyl)-5-(trifluoromethyl)-1H-pyrrole-3-carbonitrile, and has a volatile organic compound (VOC) content of not more than 400 g/L. ##STR00001## [In the formula (1), M represents zinc or copper, and R.sup.1 independently represents a hydrogen atom or a methyl group.]

The present invention relates to derivatives of , -disubstituted amide compounds which comprise a substituted aryl at the carbon such that the substituent provides a means for attachment or incorporation of the compound to or in a polymer. The provision of such a substituent on the aryl has surprisingly been found not only to permit attachment to or incorporation n a polymer but also retention of useful antifouling activity. In embodiments, the substituent is selected from hydroxyl, ethers, esters, carboxyls, alkylsilyls and alkenyls. Experiments demonstrate that antifouling activity can be as good or better as the corresponding unsubstituted compound and that polymers functionalized so as to include or be formed from the substituted compound can be used to reduce settlement.

A copolymer of triisopropylsilyl (meth)acrylate with a (meth)acrylic acid derivative having a Mn of 6,000-100,000 and a Mw/Mn of up to 2.0 is provided. A paint composition comprising the copolymer and a relatively small amount of an organic solvent has a low viscosity.

Provision of hydroxyl group functionalized quaternary ammonium halides, photocurable or hydrolytically curable urethane based polymers thereof and their use as antifouling agents.

A surface-treating agent including at least one perfluoro(poly)ether group containing silane compound of any of the formulae (A1), (A2), (B1), (B2), (C1) and (C2):

##STR00001##

wherein, each of symbols is as defined in the specification, and wherein a proportion of the perfluoro(poly)ether group containing silane compound having a molecular weight of 3,000 or less in the perfluoro(poly)ether group containing silane compounds of any of the above general formulae is 9 mol % or less.

An antifouling coating composition contains a silyl ester-based polymer and water, wherein the silyl ester-based polymer has a triorganosilyl group, the antifouling coating composition has a volatile organic compound (VOC) content of 100 g/L or less, an oxyalkylene unit is present in the antifouling coating composition, and a molar ratio ((a) (b)) of a triorganosilyl group (a) to an oxyalkylene unit (b) measured by .sup.13C-NMR with respect to the antifouling coating composition is 40.0:60.0 to 48.5:51.5.

[Problem] To provide a curable organopolysiloxane antifouling composite coating film obtained by using a urethane resin anticorrosive coating film excellent in curability instead of one or two organopolysiloxane intermediate coating film layers (Tie Coats) to layer an organopolysiloxane antifouling coating film excellent in both interlayer adhesiveness with the anticorrosive coating film and antifouling performance; and an antifouling substrate coated with the composite coating film. [Solution] An antifouling composite coating film, comprising a laminated urethane resin anticorrosive coating film and antifouling coating film, (I) the urethane resin anticorrosive coating film being formed from an anticorrosive paint composition comprising a main agent selected from the group consisting of polyols and glycidyl ethers, and an isocyanate curing agent, (II) the antifouling coating film being formed from a curable polysiloxane composition comprising specific components (a), (b), and (c).