Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Reexamination Certificate
1999-09-22
2002-10-08
Zitomer, Fred (Department: 1713)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
C106S015050, C106S018300, C106S018320, C106S018340, C106S018360, C523S177000, C525S328200, C525S337000, C525S383000, C525S509000
Reexamination Certificate
active
06462102
ABSTRACT:
TECHNICAL FIELD
The present invention relates to a resin for use in an antifouling coating to be applied to ships, fishing nets and the like, and to an antifouling coating containing said resin.
BACKGROUND ART
An aquatic life, such as barnacles, ascidians, serpulas, Saxidomus bivalves, Bugula bryozoans, green laver and sea lettuce, tends to attach itself to various bodies or structures in the water, causing various kinds of damages. For instance, attachment of such an aquatic life to the hull of a ship will reduce the velocity of the ship, causing an increase in the rate of fuel consumption. When such an aquatic life has attached itself to a fishing net or the like, they may clog meshes of the net and cause death of fish, as is well known.
Therefore, antifouling coatings are used to prevent such an aquatic life from attaching itself to those bodies or structures in the water and growing thereon. As such antifouling coatings, coatings which comprise a polymer having trialkyltin moieties as a vehicle are known. Such antifouling coatings are excellent since the rate of elution of the antifoulant can be controlled at a minimum level necessary for maintaining the antifouling effect and thus the antifoulant can be eluted at a constant rate over a long period of time.
Said antifouling coatings, when applied to ships, for instance, release the tin compound as the result of hydrolysis, in the weakly alkaline milieu of seawater, of the trialkyltin-containing polymer used as vehicle, whereupon the vehicle becomes soluble in water and the coatings are eroded and smoothened. The coatings thus contribute to reducing the resistance due to friction with seawater and reducing the rate of fuel consumption. However, for fear that the trialkyltin compound so eluted should adversely affect the ecosystem, it has been demanded that the development of antifouling coatings which have low toxicity against mammals and thus can be used safely and, at the same time, are capable of insuring the long-sustained antifouling effect.
As compounds meeting such demand, complexes of boron-containing compounds with amines are known.
For example, U. S. Pat. No. 3,211,679 (1965) discloses an antifouling composition for use in seawater which contains, as an active ingredient, not less than 25% by weight of a complex of triphenylborane with a substituted or unsubstituted pyridine of the following general formula (5):
(wherein R
8
represents a hydrogen atom, a halogen atom, a lower alkyl group, an amido group, a cyclic hydrocarbon group or a heterocyclic group), each in meta or para position, or with an aliphatic amine.
Japanese Kokai Publication Sho-39-28579 discloses, as compounds capable of inhibiting growth of microorganisms, complexes of triphenylborane (in which each phenyl group may optionally have a halogen or lower alkoxy substituent in para position), tritolylborane or trinaphthylborane with an amine having a PK
b
value of not more than 10.
Japanese Kokoku Publication Sho-54-1571 discloses tetraphenylborane complexes represented by the following general formula (6):
(wherein X represents a potassium atom, an ammonium group, or a quaternized nitrogen-containing group which may be in the form of a nitrogen-containing heterocyclic group).
Japanese Kokoku Publication Sho-62-25710 discloses, as antifoulant compounds, complexes of tetraarylboranes represented by the following general formula (7):
(wherein R
9
represents a hydrogen atom, a halogen atom or a lower alkyl group, R
10
represents a halogen atom, a lower alkyl group or a lower alkenyl group and R
11
represents a heterocyclic amine), with an ammonium or heterocyclic compound.
Japanese Kokoku Publication Sho-62-24022 discloses, as antifoulant compounds for use in underwater antifouling coatings, tetraphenylborane derivatives represented by the following general formula (8):
(wherein R
12
represents a lower alkyl group).
Japanese Kokai Publication Hei-07-133207 discloses an antifouling composition for fishing nets and implements which comprises triphenylborane-pyridine complex as an essential ingredient.
Japanese Kokai Publication Hei-08-295608 discloses an antifouling composition for fishing nets which comprises one or more triphenylborane-alkylamine complexes represented by the following general formula (9):
(wherein R
13
represents an alkyl group containing 3 to 30 carbon atoms, as active ingredients), and further an organic solvent for dissolving said active ingredients. Japanese Kokai Publication Hei-08-295609, also, discloses an antifouling composition for fishing nets which comprises an organic solvent and a complex of triphenylborane with a primary amine having an n-octadecyl group.
Japanese Kokai Publication Hei-08-295829 discloses an underwater antifouling coating which contains, as an active antifouling ingredient, a complex compound represented by the following general formula (10):
(wherein R
14
is a lower alkyl group, a lower alkoxy group or a halogen atom, n is 1, 2 or 3 and A represents a heterocyclic compound, which may optionally have a substituent or substituents selected from among lower alkyl, carboxyl, aminocarbonyl and so on, or ammonia or an amine compound of the formula R
15
R
16
NH (in which R
15
and R
16
may be the same or different and each independently represents a hydrogen atom, an alkyl group or a cyclohexyl group)).
Japanese Kokai Publication Hei-09-78007 discloses an underwater antifouling coating which contains, as an active ingredient, a triphenylborane-hydroxyalkylamine complex represented by the following general formula (11):
(wherein X represents a hydroxyalkyl group and n represents an integer of 1 to 3).
However, among the compounds referred to above, the complex of triphenylborane with pyridine or a pyridine derivative is scarcely soluble in organic solvents and, therefore, said complex component is generally contained in the coatings in a suspended state. The problem is that such coatings are difficult to handle since prolonged storage results in precipitation of said complex component.
Other complexes of boron-containing compounds with amine each is a single molecule compound and, therefore, the problem is that even when coatings are formed using a coating which contains the above-mentioned complex compound, it is difficult to control the rate of elution of said complex compound in water, so that the antifouling effect can hardly be maintained for a long period of time.
Japanese Kokai Publication Hei-11-199801 discloses an antifouling coating composition comprising a polymer containing a triarylborane coordinated to N atom as a vehicle. However, this coating composition has drawbacks that the antifouling effect can be maintained for only 3 to 6 months and that the resin itself is insufficiently self-polishing type.
On the other hand, Japanese Kokai Publication Hei-06-25560 discloses the combined use of a heavy metal compound and the copper salt of 2-pyridinethiol-1-oxide for antifouling coatings. This technology is characterized in that the antifouling coatings contain the salt of copper and a fundamental compound having the pyrithione skeleton. However, said technology intends to produce antifouling effects by merely blending such pyrithione skeleton-containing compound with a resin; it does not aim to provide the so-called functional polymer which has the basic feature of controlled hydrolysis and sustained release characteristics.
SUMMARY OF THE INVENTION
In view of the prior art mentioned above, the present invention has its object to provide a resin for use in an antifouling coating wherein an eluted antifoulant substance has low toxicity, an antifouling effect is based on a functional polymer having hydrolysis and sustained release characteristics highly controlled and very excellent antifouling effects over a long period of time are obtained, as well as an antifouling coating in which said resin is employed.
The present invention is related to a resin for use in an antifouling coating which comprises a polymer obtained by polymerizing a polymerizable unsaturated monomer(s) and having, at si
Arai Tomokazu
Kushi Yoshinori
Nakamura Isao
Yamamori Naoki
Yokoi Junji
Connolly Bove & Lodge & Hutz LLP
Nippon Paint Co. Ltd.
Zitomer Fred
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