WO2002018500A1 - Agents anti-salissures extraits d'algues marines - Google Patents
Agents anti-salissures extraits d'algues marines Download PDFInfo
- Publication number
- WO2002018500A1 WO2002018500A1 PCT/KR2001/001460 KR0101460W WO0218500A1 WO 2002018500 A1 WO2002018500 A1 WO 2002018500A1 KR 0101460 W KR0101460 W KR 0101460W WO 0218500 A1 WO0218500 A1 WO 0218500A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- methanol
- extract
- sinicola
- fraction
- ishige
- Prior art date
Links
- 239000002519 antifouling agent Substances 0.000 title claims description 19
- 241000195493 Cryptophyta Species 0.000 title description 2
- 241000631638 Ishige sinicola Species 0.000 claims abstract description 27
- 239000000284 extract Substances 0.000 claims abstract description 18
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 39
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 10
- 239000012141 concentrate Substances 0.000 claims description 6
- 239000011877 solvent mixture Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000001914 filtration Methods 0.000 claims description 4
- 239000000843 powder Substances 0.000 claims description 3
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims 2
- 239000000706 filtrate Substances 0.000 claims 2
- 239000006286 aqueous extract Substances 0.000 claims 1
- 230000003373 anti-fouling effect Effects 0.000 abstract description 14
- 239000000203 mixture Substances 0.000 abstract description 4
- 241000199919 Phaeophyceae Species 0.000 abstract description 2
- PIILXFBHQILWPS-UHFFFAOYSA-N tributyltin Chemical compound CCCC[Sn](CCCC)CCCC PIILXFBHQILWPS-UHFFFAOYSA-N 0.000 abstract 2
- 241000237536 Mytilus edulis Species 0.000 description 15
- 241000196253 Ulva prolifera Species 0.000 description 13
- 239000002032 methanolic fraction Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 7
- 238000000034 method Methods 0.000 description 5
- 239000012223 aqueous fraction Substances 0.000 description 4
- 239000010410 layer Substances 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000013535 sea water Substances 0.000 description 3
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 230000001464 adherent effect Effects 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- VLXGYEMZRIGDRH-UHFFFAOYSA-N n-[3-[4-(2-aminoethyl)-2,6-dibromophenoxy]propyl]-1-cyanoformamide Chemical compound NCCC1=CC(Br)=C(OCCCNC(=O)C#N)C(Br)=C1 VLXGYEMZRIGDRH-UHFFFAOYSA-N 0.000 description 2
- 239000003973 paint Substances 0.000 description 2
- 230000009528 severe injury Effects 0.000 description 2
- 235000015170 shellfish Nutrition 0.000 description 2
- OYDCCWNLILCHDJ-ZZXKWVIFSA-N 4-(sulfooxy)-cinnamic acid Chemical compound OC(=O)\C=C\C1=CC=C(OS(O)(=O)=O)C=C1 OYDCCWNLILCHDJ-ZZXKWVIFSA-N 0.000 description 1
- 241000251468 Actinopterygii Species 0.000 description 1
- 241000132092 Aster Species 0.000 description 1
- 241001474374 Blennius Species 0.000 description 1
- 208000006558 Dental Calculus Diseases 0.000 description 1
- 241000631928 Ishigeaceae Species 0.000 description 1
- 241000218922 Magnoliophyta Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241001643667 Orpha Species 0.000 description 1
- 241000243142 Porifera Species 0.000 description 1
- 241000098105 Pseudoceratina purpurea Species 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 241001148683 Zostera marina Species 0.000 description 1
- 239000012620 biological material Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 239000000598 endocrine disruptor Substances 0.000 description 1
- 231100000049 endocrine disruptor Toxicity 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 229940093499 ethyl acetate Drugs 0.000 description 1
- 235000019439 ethyl acetate Nutrition 0.000 description 1
- 239000002024 ethyl acetate extract Substances 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 238000005194 fractionation Methods 0.000 description 1
- 239000013505 freshwater Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 229910001385 heavy metal Inorganic materials 0.000 description 1
- 239000005556 hormone Substances 0.000 description 1
- 229940088597 hormone Drugs 0.000 description 1
- 230000001788 irregular Effects 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000000401 methanolic extract Substances 0.000 description 1
- 235000020638 mussel Nutrition 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- OYDCCWNLILCHDJ-UHFFFAOYSA-N p-sulfooxy cinnamic acid Natural products OC(=O)C=CC1=CC=C(OS(O)(=O)=O)C=C1 OYDCCWNLILCHDJ-UHFFFAOYSA-N 0.000 description 1
- 230000003449 preventive effect Effects 0.000 description 1
- 238000010298 pulverizing process Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
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
- A01N65/00—Biocides, pest repellants or attractants, or plant growth regulators containing material from algae, lichens, bryophyta, multi-cellular fungi or plants, or extracts thereof
- A01N65/03—Algae
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1612—Non-macromolecular compounds
- C09D5/1625—Non-macromolecular compounds organic
Definitions
- the present invention relates to an environment- friendly antifouling agent using extract of an alga. More particularly, antifouling activity of extract from an alga with the scientific name of Ishige sinicola, which has excellent antifouling ability.
- Antifoulant is an agent used in combination with paint to prevent adhesion and growth of marine adherent organisms (eg. sea animals, plants or microbes) on the surface of vessels and so on.
- marine adherent organisms eg. sea animals, plants or microbes
- the marine adherent organisms cause an increase in the rate of corrosion of the surface of the vessels and so on.
- the irregular surface of a vessel has a direct correlation to the frictional resistance of a ship. Hence, when such oceanic fouling organisms adhere to the surface and grow, the frictional resistance of a ship is raised. As a result, the consumption of fuel increases to bring enormous loss in expense.
- TBT Tributiltin
- U.S. Patent No. 5,607,741 discloses an antifouling agent comprising the extract from a kind of angiosperm, Zostera marina, called Zosteric acid. Also, it has been reported that Ceratinamine, extracted from a kind of sponge called Psammaplysilla purpurea, has antifouling activity. However, it was found that the antifouling actions of these substances were inadequate for practical uses.
- antifouling agents are essential substances that protect and assist in the oceanic resource development, but continuing usage of currently available antifouling agents containing tin or copper will become a threat to the marine environment and bring about fatal effects to the oceanic ecosystem in the long run.
- the object of the present invention is to provide a novel antifouling agent using the extract from a marine alga, being environment-friendly since it is extracted from biomaterial, which is capable of substituting TBT and yet is environmentally safe.
- Fig. 1 is a schematic diagram illustrating the individual step to obtain active fractions from Ishige sinicola .
- Ishige sinicola belongs to Ishigeaceae family of Ichordariales order of Phaeophyceae class of Phaeopyta phylum on the classification system and has a scientific name of Ishige sinicola (Setchell et Gardner) Chihara. This plant has a heteromorphic alternation of generation in life cycle and thallus is composed of parenchyma with different cell structures interconnected. Aster is also like the thallus with a ramified formation. The color of the thallus is a dark yellow and its surface has a slippery secretion. Ishige sinicola is found in the tropical to temperate regions, especially in the tidal zone.
- Ishige sinicola used in this invention was collected from October 1998 to July 2000 in different coastal areas of Korea, including Sokcho, Daechon, Koje Island, Wando, Busan, and Seonsanpo.
- the extraneous matters attached to the thallus of the collected ishige sinicola was carefully removed with a soft brush and the alga was washed in fresh water then dried completely at room temperature. Thereafter, the alga was finely ground, which was then .used for the test.
- the combined aqueous layer was treated with aqueous ammonia to pH 10 and extracted twice with a solvent mixture (3:1) of chloroform and methanol (5 ml) .
- the organic extract was designated as Fraction IV.
- the aqueous layer was designated as Fraction V.
- the respective fractions were then screened for their antifouling activities through examining the adhesion of Enteromorpha prolifera' s spores and the repulsion against attachment of Mytilus edulis (mussels) . Test of antifouling effect
- Enteromorpha prolifera was collected from a seaweed farm located on the coastal areas of Kimhae, Korea and Mytilus edulis was collected on the coastal areas of Busan. Enteromorpha prolifera was examined for the growth rate of its thallus and the adhesion of its spores. Mytilus edulis was examined for the repulsion against attachment of its pes and the adhesion in larvae stage.
- Ishige sinicola was used in a powder form prepared by completely drying at room temperature for 3 to 7 days and finely grinding. 1 g of dry ground Ishige sinicola was added to 50 ml of methanol and left for 1 day at room temperature. The methanol layer was separated and concentrated. About 40 mg of the concentrate was dissolved in 1 ml of methanol to form a methanol fraction, which was used for the test. The substances insoluble in methanol were added to distilled water in the same amount as methanol and left for 1 day.
- the resulting aqueous layer was separated and concentrated. A 40 mg of the concentrate was dissolved in 1 ml of distilled water to form an aqueous fraction, which was used for the test.
- a thallus of Enteromorpha prolifera was cut into pieces with a size of 5 mm and cultured for 15 days in PES (Provasoli's enrichment, Jap. Soc . Plant Physiol, 1968, 63-75) to determine its optimal growth time.
- the pieces of Enteromorpha prolifera were measured for their sizes every 2 days. On the 7 th day, the results showed the highest growth rate per day of 12.1 ⁇ 2.7%, at which the size was 9.2 ⁇ 0.7 mm.
- the methanol fraction of Ishige sinicola showed a significant preventive effect of spore adhesion. The results are shown in Table 1. Table 1
- the test for the repulsion against attachment of Mytilus edulis' pes was performed according to the method of Hyashi & Miki (J. Mar. Biotechnol . 4, 127- 130) .
- the used Mytilus edulis was cultivated and fully matured one having a size of 4.5 ⁇ 0.2 cm.
- One ⁇ l of the Ishige sinicola extract (40 mg/ml) was diluted with a 10-fold volume of seawater and examined for repulsion against attachment of Mytilus edulis' pes.
- the methanol fraction of Ishige sinicola showed a significant repulsion effect against attachment of Mytilus edulis .
- Table 2 The results are shown in Table 2.
- Test for adhesion of larvae of Mytilus edulis The test for the adhesion of larvae of Mytilus edulis was performed according to the method of Kitamura (Noppon Suisan Gakkaishi, 58, 75-78). Whatman paper was used as an attachment substrate. The Whatman filter papers were absorbed with various concentrations of methanol extract from Ishige sinicola and soaked in seawater for 4 days . In the experiment , it was observed that the adhesion of larvae of Mytilus edulis was perfectly blocked by the methanol fraction of Ishige sinicola at a concentration of more than 0.8 mg/ml. The results are shown in Table 3. The data shows the proportion of the adhered larvae to the total larvae used in the initial seawater.
- Fractionation of antifouling substances Following the procedures illustrated in Fig. 1, the dried and powdered Ishige sinicola was fractionated into Fractions I to V. Each Fraction was examined for its ability to prevent the adhesion of spores of Enteromorpha prolifera and to repulse the attachment of Mytilus edulis' pes. The results are shown in Table 4. Table 4
- the antifouling agent containing extract from a marine alga according to the present invention shows an excellent antifouling effect against oceanic fouling organisms, such as Enteromorpha prolifera and Mytilus edulis .
- This environment-friendly antifouling agent is expected to substitute for TBT which has a problem associated with disruption of ecosystems.
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Biotechnology (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Mycology (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Microbiology (AREA)
- Agronomy & Crop Science (AREA)
- Natural Medicines & Medicinal Plants (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Paints Or Removers (AREA)
Abstract
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
AU2001286280A AU2001286280A1 (en) | 2000-08-31 | 2001-08-29 | Anti-fouling agent extracted from marine algae |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
KR10-2000-0051136A KR100386417B1 (ko) | 2000-08-31 | 2000-08-31 | 해조류의 추출물을 이용한 환경 친화적인 방오제 |
KR2000/51136 | 2000-08-31 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2002018500A1 true WO2002018500A1 (fr) | 2002-03-07 |
Family
ID=19686390
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/KR2001/001460 WO2002018500A1 (fr) | 2000-08-31 | 2001-08-29 | Agents anti-salissures extraits d'algues marines |
Country Status (3)
Country | Link |
---|---|
KR (1) | KR100386417B1 (fr) |
AU (1) | AU2001286280A1 (fr) |
WO (1) | WO2002018500A1 (fr) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110119774A1 (en) * | 2007-09-20 | 2011-05-19 | Tel Hashomer Medical Research Infrastructure And S | Compositions of aquatic origin for prevention of cell adhesion and methods of using same |
CN107306998A (zh) * | 2017-06-10 | 2017-11-03 | 威海温喜生物科技有限公司 | 一种水稻专用拌种剂 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100745021B1 (ko) * | 2006-09-27 | 2007-08-01 | 신라대학교 산학협력단 | 넓패 추출물을 함유하는 여드름 피부용 화장료 조성물 |
DE102007030406A1 (de) * | 2007-06-29 | 2009-01-08 | Henkel Ag & Co. Kgaa | Verminderung der Adhäsion von biologischem Material durch Algenextrakte |
KR101528548B1 (ko) * | 2014-06-12 | 2015-06-12 | 대진건설(주) | 해조류를 이용한 고내수성 및 고접착력 친환경 도료 조성물 및 이를 이용한 도장방법 |
KR102486727B1 (ko) * | 2022-08-19 | 2023-01-10 | (주)베누스타 | 희토류를 포함하는 기능성 분말과 목초액과 해조류 농축액을 이용한 친환경 도료의 제조방법 |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991009915A1 (fr) * | 1989-12-22 | 1991-07-11 | Courtaulds Coatings (Holdings) Limited | Composition de revetement anti-fouling |
US5143545A (en) * | 1991-09-20 | 1992-09-01 | The United States Of America As Represented By The Secretary Of The Navy | Antifouling marine coatings |
US5607741A (en) * | 1992-12-11 | 1997-03-04 | Arch Development Corporation | Phenolic acid sulfate esters for prevention of marine biofouling |
US5695552A (en) * | 1993-12-09 | 1997-12-09 | Research Foundation Of State University Of New York | Aquatic antifouling compositions and methods |
US5861435A (en) * | 1994-09-16 | 1999-01-19 | Nippon Paint Co., Ltd. | Method for preventing settlement of aquatic fouling organisms |
US5989323A (en) * | 1993-12-09 | 1999-11-23 | The Research Foundation Of State University Of New York | Aquatic antifouling compositions and methods |
Family Cites Families (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0390009A (ja) * | 1989-08-31 | 1991-04-16 | Lion Corp | 藻類発生抑制物質 |
JPH08104833A (ja) * | 1994-10-03 | 1996-04-23 | Oobusu Kk | 船舶用塗料 |
JPH11180813A (ja) * | 1997-12-19 | 1999-07-06 | Ichimaru Pharcos Co Ltd | 海藻抽出物含有抗菌・防腐剤 |
JP2000119297A (ja) * | 1998-10-09 | 2000-04-25 | Marine Biotechnol Inst Co Ltd | 新規物質エピジオキシステロール |
-
2000
- 2000-08-31 KR KR10-2000-0051136A patent/KR100386417B1/ko not_active Expired - Fee Related
-
2001
- 2001-08-29 WO PCT/KR2001/001460 patent/WO2002018500A1/fr active Application Filing
- 2001-08-29 AU AU2001286280A patent/AU2001286280A1/en not_active Abandoned
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO1991009915A1 (fr) * | 1989-12-22 | 1991-07-11 | Courtaulds Coatings (Holdings) Limited | Composition de revetement anti-fouling |
US5143545A (en) * | 1991-09-20 | 1992-09-01 | The United States Of America As Represented By The Secretary Of The Navy | Antifouling marine coatings |
US5607741A (en) * | 1992-12-11 | 1997-03-04 | Arch Development Corporation | Phenolic acid sulfate esters for prevention of marine biofouling |
US5695552A (en) * | 1993-12-09 | 1997-12-09 | Research Foundation Of State University Of New York | Aquatic antifouling compositions and methods |
US5989323A (en) * | 1993-12-09 | 1999-11-23 | The Research Foundation Of State University Of New York | Aquatic antifouling compositions and methods |
US5861435A (en) * | 1994-09-16 | 1999-01-19 | Nippon Paint Co., Ltd. | Method for preventing settlement of aquatic fouling organisms |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US20110119774A1 (en) * | 2007-09-20 | 2011-05-19 | Tel Hashomer Medical Research Infrastructure And S | Compositions of aquatic origin for prevention of cell adhesion and methods of using same |
US9737571B2 (en) * | 2007-09-20 | 2017-08-22 | Tel Hashomer Medical Research Infrastructure And Services Ltd. | Compositions of aquatic origin for prevention of cell adhesion and methods of using same |
CN107306998A (zh) * | 2017-06-10 | 2017-11-03 | 威海温喜生物科技有限公司 | 一种水稻专用拌种剂 |
Also Published As
Publication number | Publication date |
---|---|
KR100386417B1 (ko) | 2003-06-02 |
AU2001286280A1 (en) | 2002-03-13 |
KR20020017653A (ko) | 2002-03-07 |
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