GB2234250A - Antifouling agent for fishnets - Google Patents
Antifouling agent for fishnets Download PDFInfo
- Publication number
- GB2234250A GB2234250A GB9006932A GB9006932A GB2234250A GB 2234250 A GB2234250 A GB 2234250A GB 9006932 A GB9006932 A GB 9006932A GB 9006932 A GB9006932 A GB 9006932A GB 2234250 A GB2234250 A GB 2234250A
- Authority
- GB
- United Kingdom
- Prior art keywords
- isothiazolone
- alkyl
- compound
- composition according
- antifouling composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom not containing sulfur-to-oxygen bonds, e.g. polysulfides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/26—Oxidation products of dithiocarbamic acid derivatives, e.g. thiuram sulfides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Thiazole And Isothizaole Compounds (AREA)
Abstract
An antifouling composition for fishnets comprises (a) a compound (I> <IMAGE> wherein Y is (C1-C18) alkyl or (C3-C12) cycloalkyl, optionally substituted with hydroxy, halo, cyano, alkylamino, dialkylamine, arylamino, carboxy, carbalkoxy, alkoxy, aryloxy, alkylthio, arylthio, haloalkoxy, cycloalkylamino, carbamoxy, or isothiazolonyl; an unsubstituted or halo-substituted (C2-C8) alkenyl or alkynyl; a (C7-C10) aralkyl optionally substituted with halogen, (C1-C4) alkyl or (C1-C4) alkoxy; or an aryl optionally substituted with halogen, nitro, (C1-C4) alkyl, (C1-C4) alkoxy, phenoxy, hydroxy, trihalomethyl, (C1-C4) alkyl-acylamino, carb (C1-C4) alkoxy or sulfamyl, and X' and X<2> are each H, (C1-C4) alkyl or halogen; and (b) one or both of (i) a compound (II> (II) R' -Sm - R' wherein each R' is (C1-C20) alkyl and m is 2 to 10; (ii) a compound (III> <IMAGE> wherein each R<2> is (C1-C4) alkyl. The combination provides antifouling with low toxicity to fish and pollution.
Description
ANTIFOULING AGENT FOR FISHNETS
The present invention relates to a heavy metal-free antifouling solution for fish nets that effectively prevents the attachment of marine fouling organisms to nets, either for use in cultivation farms or for stationary net fishery, as well as to items submerged in water such as accessories for fishnets.
Fishnets for use in cultivation farms or in stationary net fishery and ropes used with them are submerged in seawater for a prolonged period and are prone to be infested with extensive attachments of marine fouling organisms including seaweeds, barnacles, tube worms, polyzoans and mollusks. The attachment of these marine fouling organisms prevents economical use of fishnets and costs lots of labour and money in maintenance work. It has therefore been desired to develop an antifouling agent for fishnets that remains effective and economical for a prolonged period and which is simple to use without causing pollution of the environment.
With a view to attaining this objective, various studies and proposals have been made and it is generally known that a series of organotin compounds (e.g.
trialkyl or triphenyl tin compounds) are effective for practical purposes.
However, most of the previously proposed organotin compounds are highly toxic and products containing them might cause damage to users if not handled carefully. They are also disadvantageous from the viewpoint of the need to prevent environmental pollution. For thesc reasons, the advent of a heavy metaland pollution-free antifouling agent for fishnets has been strongly desired.
Japanese Patent Publication No. 50984/1986 shows an antifouling agent for marine structures that contains 3-isothiazolone as an effective ingredient.
Japanese Patent Application (OPI) No.3460411981 (the term OPI as used herein means an unexamined published Japanese patent application) shows a marine antifouling agent or an antifouling solution for fishnets that employs tetrachloroisophthalonitrile. Japanese Patent Application (OPI) No.8150511981 shows a marine antifouling agent or an antifouling solution for fishnets that employs a dialkyl sulfide or tetraalkylthiuram disulfide compound. Japanese
Patent Application (OPI) No. 118006/1981 shows a marine antifouling agent or an antifouling solution for fishnets that employs a combination of the three components mentioned above.However, these compounds, when taken individually, are not satisfactory for practical purposes since they are comparatively low in their ability to prevent attachment of marine antifouling organisms. In addition, very few of them exhibit a desired antifouling efficacy against a broad spectrum of fouling organisms. Although some of the proposals made in the above listed patents are being commercialized, there still is a need to develop an antifouling agent for fishnets that is potentially low in environmental hazard and toxicity to fish and which yet shows satisfactory results in practical applications.
In one aspect, the present invention provides an antifouling composition for fish nets comprising (a) at least one compound of the formula (I)
wherein Y is (C1-C18)alkyl or (C3-C12)cycloalkyl each optionally substituted with one or more of hydroxy, halo, cyano, alkylamino, dialkylamine, arylamino, carboxy, carbalkoxy, alkoxy, aryloxy, alkylthio, arylthio, haloalkoxy, cycloalkylamino, carbamoxy, or isothiazolonyl; an unsubstituted or halo-substituted (C2-C8)alkenyl or alkynyl; a (C7
C10)aralkyl optionally substituted with one or more of halogen, (C1-C4)alkyl or (C1
C4)alkoxy; or an aryl optionally substituted with one or more of halogen, nitro, (C1 C4)alkyl, (C -C4)alkoxy, phenoxy, hydroxy, trihalomethyl. (C1-C4)alkyl-acylamino, carb(C1-C4)alkoxy or sulfamyl, and X' and X2 are each independently H, (C1-C4)alkyl or halogen; and (b) one or both of
(i) at least one compound of the formula(ll)
(II) R'-Sm- R'
wherein each R' is independently (01-C20)alkyl and m is an integer of from 2
to 10; (i) at least one compound of the formula (III)
wherein each R2 is independently (C1-Clr)alkyl.
Preferably, the antifouling composition of the invention additionally comprises tetrachloroisophthalonitrile.
The invention also provides a method of preventing or inhibiting the growth of marine fouling organisms on fishnets submerged in water, comprising incorporating onto a fishnet a composition according to any preceding claim in an amount effective to adversely affect the growth of said marine fouling organisms.
According to the studies conducted by the present inventors, compounds of the general formulas (I), (11) and (Ill) and tetrachloroisophthalonitrile, when taken individually, are low in their ability to prevent attachment of marine antifouling organisms and hence are not satisfactory for use in practical applications.
However, when the compound (I) and one or both of the compounds (II) and (m) are used in combination, or if they are combined with tetrachloroisophthalonitrile, unexpectedly high synergistic effects are exhibited and antifouling agents that contain them show balanced effects in practical applications while presenting low toxicity to fish and minimal risk of environmental pollution.
Examples of the compound represented by the general formula (I), in which it is preferred that at least one of X' and X2 is halogen, include: 5chlorophenyl-2-n-decyl-3-isothiazolone, 5-chloro-2-phenethyl-3-isothiazolone, 4bromo-2-n-dodecyl-3-isothiazolone, 4,5-dichloro-2-n-octyl-3-isothiazolone, 4 methyl- 5-chloro-2-(4'-chlorobenzyl)-3-isothiazolone, 4,5-dichloro-2-(4'-chlorobenzyl)-3-isothiazolone, 4,5-dichloro-2.(4'-chlorophenyl)-3-isothiazolone, 4,5 dichloro.2-(2'-methoxy-3'-chlorophenyl)-3.isothiazolone, 4,5-dibromo-2-(4'chlorobenzyl)-3-isothiazolone, 4-methyl-5-chloro-2-(4'hydroxyphenyl)-3isothiazolone, 4,5-dichloro-2-n-he xyl-3-isothiazolone, and 5-chloro-2-(3',4' dichlorophenyl)-3-isothiazolone. Of course, these are not the sole examples of compound (I) that can be used in the present invention.
Examples of the compound represented by the general formula (z) include: diethyl pentasulfide, dipropyl tetrasulfide, diisopropyl trisulfide, di-t-butyl ditetrasulfide, dihexyl pentasulfide, dioctyl tetrasulfide, di-t-nonyl pentasulfide.
di-t-dodecyl pentasulfide, ditetradecyl tetrasulfide, dinonadecyl tetrasuifide, and di..tb.tyl decasulfide. Of course, these are not the sole examples of compound (eel) that can be used in the present invention.
Examples of the compound represented by the general formula (z) include: tetrae tbylthiuram disulfide, tetraisopropylthiuram disulfide, and tetra-n
butylthiuram disulfide. Of course, these are not the sole examples of compound that that can be used in the present invention.
The antifoulant composition of the invention is customarily incorporated in a solvent such as xylene1 solvent naphtha, diethylbenzene, pseudocumene, mesitylene, triethylbenzene and butyl acetate, with zylene, solvent naphtha, pseudocumene or butyl acetate being preferred.
The mixing proportions of the compound m and or both of the compounds (11) and (m), and tetrachloroisophthalonitrile if this is used, and the total amount of
their use are not limited to any values since these factors will vary both with the
antifouling performance required of the final product and with the conditions of
the environment in which it is used. Normally, these compounds and optional
tetrachloroisophthalonitrile are used in amounts giving a total active ingredient
concentration ranging from 3 to 30 parts, desirably from 8 to 20 parts, per 100 parts of
the final product.
The mixing proportions of the compound (I) and or both of the compounds (II) and (m) and the optional component tetrachloroisophthalonitrile can be varied in
accordance with the specific conditions of the environment in which the
antifouling agent of the present invention is used. Additional ingredients that
are known to be effective and safe may also be incorporated and this offers the
advantage that more balanced effects are anticipated against various marine
fouling organisms.
The antifouling solution for fishnets of the present invention can be prepared ,VltN ease. Compound (I) and one or both of the compounds (II) and (m), and optionally tetrachloroisophthalonitrile may be dissolved in solvents such as xylene, solvent naphtha and pseudocumene together with resins such as natural resins, oily resins, synthetic resin and synthetic rubber-base resins that are employed in ordinary paints, and optional additives such as colorants and plasticizers that may be incorporated as required. Advantageous resins include polyacrylics, polybutenes, rosins, coumarone resins, polyvinyl chloride, chlorinated rubbers, alkyd resins, and ethylene/vinyl acetate copolymer resins.
The following examples are given for illustrating the formulation of the antifouling agent for fishnets of the present invention. It should however be noted that the present invention is by no means limited by these examples. In the following examples, the amounts of all ingredients incorporated are expressed in weight percent.
EXAMPLE 1 4,5-Dichloro-2-n-octyl-3.isothiazolone 5% Tetraethylthiuram disulfide 10%
Acrylic resin (in 50% xylene solution) 20%
Xylene 65%
EXAMPLE 2 6-chloro-2-n-decyl-3-isothiazolone 5%
Di-t-nonyl pentasulfide 10%
Acrylic resin (in 50% xylene solution) 22%
Xylene 63%
EXAMPLE 3 4,5-Dichloro-2-(4'-chlorobenzyl)-3-isothiazolone 5%
Tetraethylthiuram disulfide 10%
Acrylic resin (in 50% xylene solution) 22%
Polybutene 5%
Xylene 48%
Pseudocumene 10%
EXAMPLE 4 4,5-Dichloro-2-(4'-chlorophenyl)-3-isothiazolone 3% 4-Methyl-5-chloro-2-(4'-hydroxyphenyl)-3-isothiazolone 29G Tetraethylthiuram disulfide 10%
Acrylic resin (in 50% zylene solution) 22%
Xylene 53%
Pseudocumene 10%
EXAMPLE 5 4-Bromo-2-n-decyl-3-isothiazolone 5%
Tetraethylthiuram disulfide 6% Di-Sdodecyl pentasulfide 6%
Acrylic resin (in 50% xylene solution) 22%
Coumarone 3%
Xylene 58%
EXAMPLE 6 4-Methyl- 5.chloro-2.(4'chlorobenzyl)-3-isothiazolone 5%
Tetraethylthiuram disulfide 6%
Di-t-nonyl pentasulfide 6%
Acrylic resin (in 50% xylene solution) 22%
Xylene 51%
Pseudocumene 10%
EXAMPLE 7 4,5-Dichloro-2-n-octyl-3-isothiazolone 3% 5.Chloro-2-phenethyl-3-isothiazolone 2%
Tetraethylthiuram disulfide 6%
Di-t-nonyl pentasulfide 6%
Acrylic resin (in 50% xylene solution) 22%
Xylene 61%
EXAMPLE 8 4,5-Dichloro-2-n-octyl-3-isothiazolone 5%
Di-t-nonyl pentasulfide 5%
Tetrachloroisophthalonitrile 5%
Acrylic resin (in 50% xylene solution) 22%
Xylene 43%
Pseudocumene 20%
EXAMPLE 9 4,5-Dichloro-2-(4'-chlorophenyl)-3-isothiazolone 5% Di.t-nonyl pentasulfide 5%
Tetrachloroisophthalonitrile 5%
Acrylic resin (in 50% xylene solution) 22%
Xylene 43%
Pseudocumene 20%
EXAMPLE 10 4,5-Dichloro-2-(4'-chlorobenzyl)-3-isothiazolone 5%
Tetraethylthiuram disulfide 5%
Tetrachloroisophthalonitrile 5%
Acrylic resin (in 50% xylene solution) 22%
Xylene 43%
Pseudocumene 20% EXAMPLE 11 4,5-Dichloro-2-n-hexyl-3-isothiazolone 3% 4,5-Dichloro-2-n-tridecyl-3-isothiazolone 296 Tetraethylthiuram disulfide 5% Tetrachloroisophthalonitrile 5%
Acrylic resin (in 50% xylene solution) 22%
Xylene 43%
Pseudocumene 20% EXAMPLE 12 4,5-Dichloro- 2-n-octyl-3-isothiazoione 5%
Di-t-nonyl pentasulfide 3%
Tetraethylthiuram disulfide 3%
Tetrachloroisophthalonitrile 5%
Acrylic resin (in 50% xylene solution) 22%
Xylene 42%
Pseudocumene 20%
The efficacy of the above-noted formulations of antifouling agent was tested in the experiment described below. As comparisons, the following formulations were also tested for their efficacy.
COMPARATIVE EXAMPLE 1 4,5-Dichloro-2-n-octyl-3-isothiazolone 15%
Acrylic resin (in 50% xylene solution) 22%
Xylene 63%
COMPARATIVE EXAMPLE 2 4,5-Dichloro-2-(4'-chlorobenzyl)-3-isothiazolone 15%
Acrylic resin (in 50% xylene solution) 22%
Xylene 63% COMPARATIVE EXAMPLE 3 5.Chloro-2-phenethyl-3-isothiazolone 15% Acrylic resin (in 50% xylene solution) 22%
Xylene 63%
COMPARATIVE EXAMPLE 4 4,5-Dichloro-2-n-hexyl-3-isothiazolone 5% 4,5-Dichloro-2-n-tridecyl-3-isothiazolone 10%
Acrylic resin (in 50% xylene solution) 22%
Xylene 63%
EXPERIMENT
Polyethylene fishnets (6 knots, 400 dJ60 yarns) were dip-coated with the antifouling formulations prepared in Examples 1 - 12 and Comparative Examples 1 - 4.After being dried with air, the nets were submerged about 1 m below sea level in Tanabe Bay, Kii, Wakayama, Japan in early September of 1987 and held there for 4 months in order to investigate the time-dependent attachment of marine fouling organisms on the nets. The results were evaluated by the following criteria.
Rating Attachment of fouling organisms 1 none 2 less than 18 3 lessthan5% 4 from 5% to less than 10% 5 10-20% 6 20-50% 7 more than 50% The results are shown in Table 1 below.
TABLE 1
Time (month) 1 2 3 4 Formulation Example 1 1 2 2 3 2 1 2 3 4 3 1 2 2 3 4 1 2 3 4 5 1 2 3 4 6 1 1 2 3 7 1 1 2 3 8 1 1 2 3 9 1 1 2 3 10 1 1 2 3 11 1 1 2 3 12 1 1 1 1 Comparative Example 1 4 5 7 2 4 5 7 3 4 5 7 - 4 4 5 7 Untreated 7 - - - As the data in Table I shows, the formulations that incorporated the compound (I) and one or both of the compounds (II) and (III), or those which contained tetrachloroisophthalonitrile in addition to these compounds provided high-performance antifouling agents for fishnets that exhibited persistent synergistic effects against attachment of marine antifouling organisms in a balanced and hence practically effective way while ensuring much improved safety by causing only low toxicity to fish.
Claims (9)
1. Antifouling composition for fishnets comprising (a) at least one compound of the formula (I)
wherein Y is (C1-C18)alkyl or (C3-C12)cycloalkyl each optionally substituted with one or more of hydroxy, halo, cyano, alkylamino, dialkylamine, arylamino, carboxy, carbalkoxy, alkoxy, aryloxy, alkylthio, arylthio, haloalkoxy, cycloalkylamino, carbamoxy, or isothiazolonyl; an unsubstituted or halo-substituted (C2-C8)alkenyl or alkynyl; a (C7
C10)aralkyl optionally substituted with one or more of halogen, (C1-C4)alkyl or (C1
C4)alkoxy; or an aryl optionally substituted with one or more of halogen, nitro, (C1 C4)alkyl, (C1-C4)alkoxy, phenoxy, hydroxy, trihalomethyl, (C1-C4)alkyl-acylamino, carb(C1-C4)alkoxy or sulfamyl, and X' and X2 are each independently H, (C-C4)alkyl or halogen; and (b) one or both of
(i) at least one compound of the formula(ll)
(II) R'- Sm- R'
wherein each R' is independently (C-C20)alkyl and m is an integer of from 2
to 10; (i) at least one compound of the formula(lll)
wherein each R2 is independently (c1-c4)alkyl.
2. Antifouling composition according to Claim 1, further comprising tetrachloroisophthalonitrile
3. Antifouling composition according to Claim 1 or 2, wherein at least one of X' and X2 in the compound of formula (I) is halogen.
4. Antifouling composition according to any preceding Claim, wherein said at least one compound of formula (I) is one or more of 5-chlorophenyl-2-n-decyl-3-isothiazolone, 5-chloro-2-phenethyl-3-isothiazolone, 4-bromo-2-n-dodecyl-3-isothiazolone, 4,5dichloro-2-n-octyl-3-isothiazolone, 4-methyl-5-chloro-2-(4'-chlorobenzyl)-3isothiazolone, 4,5-dichloro-2-(4'-chloro-benzyl)-3-isothiazolone, 4,5-dichloro-2 (4'-chlorophenyl)-3-isothiazolone, 4,5-dichloro-2-(2'-methoxy-31-chlorophenyl)- 3-isothiazolone, 4,5-dibromo-2-(4'-chlorobenzyl)-3-isothiazolone, 4-methyl-5chloro-2-(4'hydroxyphenyl)-3-isothiazolone, 4,5-dichloro-2-n-hexyl-3isothiazolone, or 5-chloro-2-(3',4'-dichlorophenyl)-3-isothiazolone.
5. Antifouling composition according to any preceding Claim, wherein said at least one compound of formula (II) is one or more of diethyl pentasulfide, dipropyl tetrasulfide, diisopropyl trisulfide, di-t-butyl ditetrasulfide, dihexyl pentasulfide, dioctyl tetrasulfide, di-t-nonyl pentasulfide, di-t-dodecyl pentasulfide, ditetradecyl tetrasulfide, dinonadecyl tetrasulfide, and di-t-butyl decasulfide.
6. Antifouling composition according to any preceding Claim wherein said at least one compound of the formula (III) is one or more of tetraethylthiuram disulfide, tetraisopropylthiuram disulfide, and tetra-n-butylthiuram disulfide.
7. Antifouling composition according to any preceding Claim further comprising a solvent which is one or more of xylene, solvent naphtha, diethylbenzene, pseudocumene, mesitylene, triethylbenzene and butyl acetate.
8. Antifouling composition according to any preceding Claim wherein the total amount of the compounds of formulae (I), (II) and/or (III) and, if present, tetrachloroisophthalonitrile, in the composition is from 3 to 30 parts by weight, preferably from 8 to 20 parts by weight.
9. A method of preventing or inhibiting the growth of marine fouling organisms on fishnets submerged in water, comprising incorporating onto a fishnet a composition according to any preceding Claim in an amount effective to adversely affect the growth of said marine fouling organisms.
1 0. Antifouling composition for fishnets substantially as hereinbefore described.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP1074924A JP2790309B2 (en) | 1989-03-29 | 1989-03-29 | Aquatic fouling organism adhesion inhibitor |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| GB9006932D0 GB9006932D0 (en) | 1990-05-23 |
| GB2234250A true GB2234250A (en) | 1991-01-30 |
| GB2234250B GB2234250B (en) | 1992-04-08 |
Family
ID=13561403
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB9006932A Expired - Fee Related GB2234250B (en) | 1989-03-29 | 1990-03-28 | Antifouling agent for fishnets |
Country Status (5)
| Country | Link |
|---|---|
| JP (1) | JP2790309B2 (en) |
| KR (1) | KR0143560B1 (en) |
| CA (1) | CA2012308A1 (en) |
| GB (1) | GB2234250B (en) |
| SG (1) | SG64892G (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2255343A (en) * | 1991-01-31 | 1992-11-04 | Rohm & Haas | Improvements relating to marine stainproofing agents |
| US5472483A (en) * | 1994-11-18 | 1995-12-05 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
| EP0712576A1 (en) * | 1994-11-21 | 1996-05-22 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115340626B (en) * | 2022-10-07 | 2024-05-24 | 广东省漆色彩新型材料有限公司 | Sterilization and antifouling resin grafted with phenolic isothiazolinone acrylate monomer and preparation method thereof |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4127687A (en) * | 1976-07-19 | 1978-11-28 | Rohm And Haas Company | Prevention of fouling of marine structures such as boat hulls |
| JPS5634604A (en) * | 1979-08-29 | 1981-04-06 | Yoshitomi Pharmaceut Ind Ltd | Antifouling agent |
| JPS5681505A (en) * | 1979-12-06 | 1981-07-03 | Yoshitomi Pharmaceut Ind Ltd | Antifouling solution for fishing net |
| JPS56118006A (en) * | 1980-02-23 | 1981-09-16 | Yoshitomi Pharmaceut Ind Ltd | Antifouling solution for fish net |
| JPS62115072A (en) * | 1985-11-13 | 1987-05-26 | Nippon Paint Co Ltd | Underwater antifouling paint |
-
1989
- 1989-03-29 JP JP1074924A patent/JP2790309B2/en not_active Expired - Lifetime
-
1990
- 1990-03-15 CA CA 2012308 patent/CA2012308A1/en not_active Abandoned
- 1990-03-22 KR KR1019900003898A patent/KR0143560B1/en not_active IP Right Cessation
- 1990-03-28 GB GB9006932A patent/GB2234250B/en not_active Expired - Fee Related
-
1992
- 1992-06-27 SG SG64892A patent/SG64892G/en unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2255343A (en) * | 1991-01-31 | 1992-11-04 | Rohm & Haas | Improvements relating to marine stainproofing agents |
| GB2255343B (en) * | 1991-01-31 | 1994-04-06 | Rohm & Haas | Improvements relating to marine stainproofing agents |
| US5472483A (en) * | 1994-11-18 | 1995-12-05 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
| EP0712576A1 (en) * | 1994-11-21 | 1996-05-22 | Asahi Denka Kogyo Kabushiki Kaisha | Antifouling agent |
Also Published As
| Publication number | Publication date |
|---|---|
| GB9006932D0 (en) | 1990-05-23 |
| KR900013853A (en) | 1990-10-22 |
| GB2234250B (en) | 1992-04-08 |
| CA2012308A1 (en) | 1990-09-29 |
| JP2790309B2 (en) | 1998-08-27 |
| KR0143560B1 (en) | 1998-07-15 |
| SG64892G (en) | 1992-10-02 |
| JPH02255605A (en) | 1990-10-16 |
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| Date | Code | Title | Description |
|---|---|---|---|
| PCNP | Patent ceased through non-payment of renewal fee |
Effective date: 19980328 |