Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From boron reactant having at least one boron to hydrogen or...
Reexamination Certificate
2002-03-27
2004-06-22
Moore, Margaret G. (Department: 1712)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From boron reactant having at least one boron to hydrogen or...
C526S239000, C525S360000
Reexamination Certificate
active
06753397
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a resin composition comprising a boron-containing polymer and in particular to a resin composition comprising a boron-containing polymer useful as an antifouling coating.
BACKGROUND OF THE INVENTION
Aquatic creatures such as barnacles, ascidians, pylopagurus serpulophilus, blue mussels, bugula neritina, green layer and sea lettuce adhere to various substances below the water surface, to cause a wide variety of damage. For example, when these aquatic creatures adhere to the body of a ship, the velocity of the ship is lowered and the fuel cost is increased. Further, it is known that when the aquatic creatures adhere to fishing nets etc., the net maybe clogged to cause death of fish.
For preventing adhesion and growth of aquatic creatures on substances below the water surface, an antifouling coating is used, and there has been used an anti fouling coating comprising seawater-insoluble vinyl resin and alkyd resin as binder resin and a trialkyl tin polymeric compound as a vehicle. However, there is anxiety about the adverse effect of the eluted trialkyl tin on the ecosystem, so there is demand for development of heavy metal-free antifouling coatings and antifouling agents.
Japanese Kokai Publication Hei-7-133207 discloses triphenyl borane-pyridine derivative complex compounds. Further, triphenyl borane-fatty amine complex compounds (Japanese Kokai Publication Hei-8-295608, Japanese Kokai Publication Hei-8-295609 etc.), triphenyl borane-hydroxyl group-containing amine complex compounds (Japanese Kokai Publication Hei-9-78007), triphenyl borane-higher fatty secondary or tertiary amine complex compounds (Japanese Kokai Publication Hei-10-182322) etc. are also proposed.
For the purpose of expressing an antifouling effect for a prolonged period of time with good coating workability, Japanese Kokai Publication Hei-11-322763 discloses triphenyl borane-alkoxyl group-containing amine complex compounds, and Japanese Kokai Publication Hei-11-323206 discloses triphenyl borane-(iso)nicotinate complex compounds.
Further, Japanese Kokai Publication Hei-11-199801 discloses, as a resin composition for heavy metal-free antifouling coatings, an antifouling coating composition comprising N atom-coordinated triaryl borane-containing polymer as a vehicle.
SUMMARY OF THE INVENTION
The object of the present invention is to provide a resin composition comprising a boron-containing polymer useful as an antifouling coating which does not contain heavy metal from an environmental viewpoint.
Thus, the present invention provides a resin composition
which comprises a boron-containing polymer having, in a side chain or at a terminal thereof, at least one group represented by the following formula (1):
in the formula, R
1
is a part of an acid group; R
2
groups are the same or different and each represents a substituted or unsubstituted alkyl or aryl; X represents an oxygen or sulfur atom; Y represents a primary to tertiary amine or a heterocyclic compound containing a substituted or unsubstituted nitrogen atom; and n is 1 or 2.
Preferably, the above R
1
is represented by the following formula (2).
Further, the present invention provides a production method of a boron-containing polymer
which comprises a step of reacting a polymer having at least one acid group in a side chain or at a terminal thereof, with a nitrogen atom-coordinated boron compound represented by the following formula (3):
in the formula, R
2
groups are the same or different and each represents a substituted or unsubstituted alkyl or aryl; and Y represents a primary to tertiary amine or a heterocyclic compound containing a substituted or unsubstituted nitrogen atom.
Preferably, the above acid group is a carboxylic acid group, a sulfonic acid group or a phosphoric acid group.
Furthermore, the present invention provides a production method of a boron-containing polymer
which comprises a step (I) of reacting a polymerizable organic acid with a nitrogen atom-coordinated boron compound represented by the following formula (3):
in the formula, R
2
groups are the same or different and each represents a substituted or unsubstituted alkyl or aryl; and Y represents a primary to tertiary amine or a heterocyclic compound containing a substituted or unsubstituted nitrogen atom,
and a step (II) of polymerizing a monomer component comprising a boron-containing polymerizable monomer obtained in said step (I).
Preferably, said polymerizable organic acid is a polymerizable organic carboxylic acid, a polymerizable organic sulfonic acid or a polymerizable organic phosphoric acid.
Moreover, the present invention provides a resin composition
which comprises a boron-containing polymer obtainable by the above production method of the boron-containing polymer.
Moreover, the present invention provides an antifouling coating
which comprises the above resin composition.
DETAILED DESCRIPTION OF THE INVENTION
The resin composition of the present invention comprises a boron-containing polymer having at least one group represented by the above formula (1) in a side chain or at a terminal thereof.
In the above formula (1), R
1
represents a part of an acid group. The above R
1
is preferably a part of carboxylic acid group, sulfonic acid group or phosphoric acid group represented by the above formula (2). The R
1
is more preferably a part of carboxylic acid group.
The above R
1
constitutes an acid group in the form of —R
1
(X—H)n.
The above X represents an oxygen or sulfur atom. It is preferably an oxygen atom.
In the above formula (1), n is 1 or 2. When a part of acid group as the above R
1
is a part of phosphoric acid group, n can be 2.
In the above formula (1), R
2
groups are the same or different and each represents a substituted or unsubstituted alkyl or aryl. The above alkyl group may be linear or branched.
The number of carbon atoms in the alkyl or aryl group is preferably 1 to 30. If the number of carbon atoms is 30 or more, the antifouling property will be deteriorated when the composition is incorporated into an antifouling coating so that it will be necessary to be incorporated in a large amount, in some cases. Further, the resulting resin composition may be hardly dissolved in an organic solvent and is inferior in handling properties. The number of carbon atoms therein is more preferably 1 to 20.
The substituent group on the above alkyl or aryl includes an alkyl group, carboxyl group, sulfonic acid group, phosphoric acid group, hydroxyl group, alkoxyl group, halogen, nitro group, carbonyl group, amino group, etc. These may be linear or branched.
The above alkyl and substituted alkyl are not particularly limited, and include, for example, methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, etc. The above aryl and substituted aryl include a phenyl group, tolyl group, xylyl group, etc. The phenyl group is preferable from the viewpoint of the antifouling property.
In the above formula (1), Y represents a primary to tertiary amine or a heterocyclic compound containing a substituted-or unsubstituted nitrogen atom.
The above primary to tertiary amine is not particularly limited, and includes, for example, alkyl group-containing amines such as octadecyl amine, capryl amine, lauryl amine, myristyl amine, stearyl amine, dimethyl amine, triethyl amine etc.; acyl group-containing amines such as acetyl amine etc.; alkoxyl group-containing amines such as 3-ethoxypropyl amine, ethoxymethyl amine etc.; aryl group-containing amines such as aniline, hexyl aniline etc.; allyl amine, vinyl amine, aminostyrene, etc.
The above heterocyclic compound containing a nitrogen atom may be polycyclic where one ring is preferably a 4- to 10-memberred ring. The heterocyclic compound can also contain an oxygen atom and/or a sulfur atom as the hetero atom in addition to the nitrogen atom thereof, and the number of hetero atoms including the nitrogen atom may be 1 to 4.
In the relationship with the above primary to tertiary amine, the heterocyclic compound containing a nitrogen atom refers to the one having the nitrogen atom as a hetero a
Nakamura Isao
Yamamori Naoki
Moore Margaret G.
Nippon Paint Co. Ltd.
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