CN106700787A - Environmentally-friendly ocean antifouling paint based on self-polishing polymer/butenolide and derivatives thereof - Google Patents

Environmentally-friendly ocean antifouling paint based on self-polishing polymer/butenolide and derivatives thereof Download PDF

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Publication number
CN106700787A
CN106700787A CN201610011805.5A CN201610011805A CN106700787A CN 106700787 A CN106700787 A CN 106700787A CN 201610011805 A CN201610011805 A CN 201610011805A CN 106700787 A CN106700787 A CN 106700787A
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environment
polymer
butenolide
friendly
fouling agent
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钱培元
马春风
李泳新
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CHINA OCEAN MINERAL RESOURCES R&D ASSOCIATION
Hong Kong University of Science and Technology HKUST
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CHINA OCEAN MINERAL RESOURCES R&D ASSOCIATION
Hong Kong University of Science and Technology HKUST
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    • 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
    • C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
    • C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/20—Carboxylic acid amides
    • 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
    • C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
    • C09D143/04—Homopolymers or copolymers of monomers containing silicon
    • 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
    • C09D193/00—Coating compositions based on natural resins; Coating compositions based on derivatives thereof
    • C09D193/04—Rosin
    • 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
    • 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
    • C09D5/1637—Macromolecular compounds
    • C09D5/165—Macromolecular compounds containing hydrolysable groups
    • 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
    • C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
    • C09D5/1662—Synthetic film-forming substance
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/61—Additives non-macromolecular inorganic
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2248—Oxides; Hydroxides of metals of copper
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2265—Oxides; Hydroxides of metals of iron
    • C08K2003/2272—Ferric oxide (Fe2O3)
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2296—Oxides; Hydroxides of metals of zinc
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2205/00—Polymer mixtures characterised by other features
    • C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
    • C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Inorganic Chemistry (AREA)
  • Paints Or Removers (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)

Abstract

The invention discloses a preparation method and application of an environmentally-friendly ocean antifouling paint based on self-polishing polymer/butenolide and derivatives thereof. Controlled release of an environmentally-friendly anti-fouling agent in the paint serves as the main line, the used polymer is self-polishing polymer which can achieve self-refreshing through side group hydrolysis-polymer ablation in the ocean environment, and the fact that the anti-fouling agent can be released continuously and constantly. The used anti-fouling agent is prepared through artificial synthesis by referring to the chemical structure of marine streptomyces metabolite, and the problem that the natural anti-fouling agent has low content in living bodies, and is complex in extraction process and low in yield is overcome. Especially, the anti-fouling agent has short half-life period in the ocean and can be degraded easily, and can be degraded into non-toxic compounds quickly after being released to seawater, and is not accumulated in the living bodies. The problems that the conventional anti-fouling agent pollutes the environment and destroys the marine ecological balance and the like are overcome. The environmentally-friendly ocean antifouling paint based on self-polishing polymer/butenolide and derivatives thereof has significant application prospects in the field of environmentally-friendly ocean antifouling paint.

Description

It is a kind of based on from polishing polymer/butenolide and its derivative it is environment-friendly Marine antifouling coating
Technical field
It is more particularly to a kind of based on polishing polymer/butenolide certainly the present invention relates to a kind of marine antifouling coating And its preparation method and application of the environment-friendly marine antifouling coating of derivative；The application mainly marine antifouling coating technology Field.
Background technology
Marime fouling refers to that marine microorganism and animals and plants grow the biology to be formed in hull or marine facility adsorption Dirt, it is to ocean shipping and the exploration of marine resources, exploitation, using bringing many adverse effects。According to incompletely statistics, it is complete at present The annual economic loss caused by marine biofouling in the world reaches multi-billion dollar.Marine biofouling has turned into restriction ocean Economic development and one of technical bottleneck of coast defence safety is safeguarded, be domestic and international marine field all problem demanding prompt solutions.Organotin Class killing livestock property material is effective antifouling paint, but such coating has been prohibitted the use of because of destruction marine ecology.Development environment friend Good antifouling paint is imperative.Wherein, it is important research side to find new, low toxicity or nontoxic anti-fouling activity material To.But, although having filtered out various environment-friendly anti-fouling agents at present, it can also reach validity, wide spectrum in laboratory Property and hypotoxicity, but because effect of antifouling phase is too short and can not be applied in sea experimentation.Its key restriction factors is：Such as What solves the compatibility and controlled release of the anti-fouling agent and coating resin, realize low content effectively etc..
Summary of the invention
The purpose of the present invention is directed to the deficiency of existing antifouling paint and technology, there is provided one kind based on from polishing polymer/ Environment-friendly marine antifouling coating of butenolide and its derivative and preparation method thereof.
Another object of the present invention is to provide a kind of solution bioantifouling agent and coating resin compatibility and controlled release Method and its application.
It is a kind of based on anti-from the environment-friendly ocean of polishing polymer/butenolide and its derivative that the present invention is provided Dirty coating, has considered the anti-fouling system being made up of macromolecule matrix material and anti-fouling agent, especially pays close attention to anti-fouling agent with height The matching of molecule resin.Transformed from polishing polymer and to natural anti-fouling agent structure by the way that selection is suitable, solved Both compatibilities and its controlled release, so that natural products base anti-fouling agent slowly can be released constantly from coating Put, reach the purpose of long-acting and anti-fouling.Due to the system in marine environment will play from polishing polymer surface self refresh and The antibiont attachment double action of Marine Natural Product Antifoulants agent, makes antifouling capacity, antifouling time further improve, in green ring Protect, high-performance marine antifouling paint aspect has very important application.
The purpose of the present invention is achieved through the following technical solutions：
From polishing polymer：10~89.9 weight portions
The weight portion of butenolide or derivatives thereof 0.1~50
The weight portion of composite anti-fouling agent 0~50
The weight portion of color stuffing 0~20
The weight portion of auxiliary agent 0~10
The weight portion of solvent 10~20
Described is acrylic acid copper, zinc acrylate resin and acrylic silane ester polymer (formula 1) from polishing polymer, and X group is Zn-OCOR or Cu-OCOR, R group is-C2H5,C4H9,C7H15,C6H5,C6H11,C19H29Deng；X can also be-SiR3, R for- CH3,C2H5,C3H7or C4H9Deng.
Formula 1：From the structural formula of polishing antifouling polymer
The butenolide structural formula be formula 2 shown in,
Formula 2：The structural formula (n values are 1~6) of butenolide class anti-fouling agent
The butenolide derivant structure formula is：
Formula 3：Butenolide derivant structure formula (n=1~6)
The composite anti-fouling agent is cuprous oxide, cuprous sulfocyanide, copper pyrithione, ZPT, pyridine for described in Triphenylborane, 4,5- dichloro-s-Kathon, medetomidine, 2- (p- chlorphenyl) -3- cyano group - 4- bromos -5- trifluoromethyls-pyrroles, one or more in 2,4,6- trichlorophenyls-N-phenylmaleimide.
The auxiliary agent is chlorinated paraffin, rosin, dioctyl phthalate, castor oil, bentonite, polyamide wax, gas phase One or more in silica.
The solvent is dimethylbenzene, n-butanol, methyl iso-butyl ketone (MIBK), butanone, DAA, the one kind in vinylacetate Or it is various.
Compared with prior art, the present invention has advantages below and beneficial effect：
(1) present invention serves as theme around how solving controlled release of the bioantifouling agent in coating, the polymerization for being used Thing is that the polymer can be by side base hydrolysis in the seawater so that it becomes hydrophilic by hydrophobic from polishing polymer, With the carrying out of hydrolysis, surface is fallen off so as to realize self-renewing, so as to ensure that anti-fouling agent energy continued for constant discharges.Solve Existing antifouling paint film forming matter is not exclusively adapted to the bonding of novel antifouling agent so that anti-fouling agent effect cannot fully demonstrate this One problem.
(2) anti-fouling agent used in the present invention is transformed by the chemical constitution to marine streptomyces metabolin, can With by artificial synthesized such antifouling active compounds or its analogue, so as to solve natural products anti-fouling agent in biology Content is relatively low in body, extraction process is complicated, low-yield the problems such as.
(3) half-life short, degradable in ocean of the anti-fouling agent in the present invention, being released to after seawater can quickly decompose or drop It is non-toxic compound to solve, and is not built up in vivo.Toxic action of the conventional antifouling agents to aufwuch is overcome, and Pollution environment, destruction marine ecology has very important application preceding the problems such as balance in environment-friendly marine antifouling coating field Scape.
Brief description of the drawings
Fig. 1 shows first ocean board experiment result, is tested in Hong Kong Waters in 2015.2-2015.10.
Fig. 2 shows butenolide class anti-fouling agent release rate from polymer.
Fig. 3 shows second ocean board experiment result, is tested in Hong Kong Waters in 2015.2-2015.10.
Fig. 4 shows the 3rd ocean board experiment result, is tested in Hong Kong Waters in 2015.2-2015.10.
The content of the invention and specific embodiment
To more fully understand the present invention, the present invention is described in further detail with reference to embodiment, but the present invention Implementation method not limited to this.
Embodiment 1
95g zinc acrylate polymers, 5g butenolides are mixed with the stirring of 20g dimethylbenzene, antifouling paint is made, according to GB/T5370-2007《Anti-fouling paint model shallow sea soak test method》, carried out in Hong Kong Waters during 2015.2 to 2015.10 Shallow sea panel experiment, as a result as shown in Figure 1.Hanging plate photo in figure shows sample 8 months without marine organism growth, illustrates base Hanging plate photo display sample in antifouling paint prepared by the anti-fouling agent has good antifouling figure is given birth to for 8 months without marine organisms Effect long.
Zinc acrylate resin of the invention has good butenolide release rate from polymer is polished.Fig. 2 is bent release rate The comparing of line, for non-reactive polymer such as methyl methacrylate, butenolide substantially no longer discharges after 7 days, Even if adding soluble rosin, it also is difficult to be discharged into briny environment.Polymer is polished certainly for zinc acrylate resin, its energy 60 Its successor so can steadily discharge.
Embodiment 2
35g zinc acrylate polymers, 10g butenolides, 10g zinc oxide, 2g iron oxide reds and 20g dimethylbenzene are stirred Mixing is mixed, antifouling paint is made, by way of brushing, the film forming on epoxy resin board exists in 2015.2 to 2015.10 periods Hong Kong Waters have carried out shallow sea panel experiment, as a result as shown in Figure 3.Hanging plate photo display sample in figure is given birth to for 8 months without ocean Thing grows.
Embodiment 3
By 15g acrylic silanes ester polymer, 5g butenolides, 20g cuprous oxide, 8g zinc oxide, 2g iron oxide reds And the stirring mixing of 20g MEKs, antifouling paint is made, by way of brushing, the film forming on epoxy resin board, in 2015.2 Shallow sea panel experiment is carried out in Hong Kong Waters to 2015.10 periods, as a result as shown in Figure 4.Hanging plate photo display sample in figure This 8 months without marine organism growth.
Embodiment 4
25g copper acrylate polymers, 10g butenolides, 15g zinc oxide, 1g iron oxide reds and 20g dimethylbenzene are stirred Mixing is mixed, antifouling paint is made, by way of brushing, the film forming on epoxy resin board has carried out shallow sea extension in Hong Kong Waters Plate tests (2015.2-2015.10), and 8 months without marine organism growth.
Embodiment 5
By 10g zinc acrylate polymers, 10g rosin, 30g butenolides, 10g zinc oxide, 2g iron oxide reds and 20g Dimethylbenzene stirring mixing, is made antifouling paint, and by way of brushing, the film forming on epoxy resin board is carried out in Hong Kong Waters Shallow sea panel experiment (2015.2-2015.10), 8 months without marine organism growth.
Above-described embodiment is the present invention preferably implementation method, but embodiments of the present invention are not by the embodiment Limitation, it is other it is any without departing from Spirit Essence of the invention and the change, modification, replacement made under principle, combine, simplification, Equivalent substitute mode is should be, is included within protection scope of the present invention.For example, using the composition of present disclosure, Its content can change within the specific limits, or add other auxiliary materials or carrier equivalent etc..It is presently disclosed with can Produced with any of conventional preparation method for coating, the material composition for being used can voluntarily pacify conventional method and prepare or from market Purchase.Change in terms of these is all without departing from Spirit Essence of the invention and principle.

Claims (7)

1. a kind of based on the environment-friendly marine antifouling coating for polishing polymer/butenolide and its derivative certainly, its feature It is that it is comprising following components：
2. environment-friendly marine antifouling coating according to claim 1, it is characterised in that from polishing antifouling polymer be third Olefin(e) acid copper, zinc acrylate resin and acrylic silane ester polymer (formula 1),
Wherein, X group is Zn-OCOR or Cu-OCOR, and R group is-C2H5,C4H9,C7H15,C6H5,C6H11,C19H29Deng；Or X for- SiR3, R is-CH3,C2H5,C3H7orC4H9。
3. environment-friendly marine antifouling coating according to claim 1, it is characterised in that the butenolide structural formula It is the compound of formula 2,
4. environment-friendly marine antifouling coating according to claim 1, it is characterised in that the butenolide derivative Structural formula is formula 3：
Wherein n=1~6.
5. environment-friendly marine antifouling coating according to claim 1, it is characterised in that the composite anti-fouling agent is described It is cuprous oxide, cuprous sulfocyanide, copper pyrithione, ZPT, triphenylboron pyridine alkane, 4,5- dichloro- -2- are just pungent Base -4- isothiazoline -3- ketone, medetomidine, 2- (p- chlorphenyl) -3- cyano group -4- bromos -5- trifluoromethyls-pyrroles, 2,4, One or more in 6- trichlorophenyls-N-phenylmaleimide.
6. environment-friendly marine antifouling coating according to claim 1, it is characterised in that the auxiliary agent is chlorinated paraffin, pine Perfume (or spice), dioctyl phthalate, castor oil, bentonite, polyamide wax, one or more in aerosil.
7. environment-friendly marine antifouling coating according to claim 1, it is characterised in that the solvent is dimethylbenzene, positive fourth Alcohol, methyl iso-butyl ketone (MIBK), butanone, DAA, one or more in vinylacetate.
CN201610011805.5A 2015-11-12 2016-01-05 Environmentally-friendly ocean antifouling paint based on self-polishing polymer/butenolide and derivatives thereof Pending CN106700787A (en)

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US201562254695P 2015-11-12 2015-11-12
US62/254,695 2015-11-12

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111040087A (en) * 2019-12-31 2020-04-21 常州大学 Preparation method of self-polishing antifouling resin
CN111218187A (en) * 2020-03-06 2020-06-02 中国科学院宁波材料技术与工程研究所 Environment-friendly fluorine-silicon modified acrylic acid antifouling paint with micro-nano-like structure, and preparation method and application thereof
CN115109449A (en) * 2021-03-18 2022-09-27 香港科技大学 Antifouling compound BOC-butenolide with potent ability to inhibit adhesion of marine invertebrate larvae
CN116240728A (en) * 2022-12-30 2023-06-09 佛山港科涂工技术有限公司 Water-based bionic environment-friendly antifouling paint and preparation method and application thereof

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CN101550305A (en) * 2008-04-02 2009-10-07 上海海悦涂料有限公司 Long-life self-polishing antifouling coating
CN102105542A (en) * 2008-07-24 2011-06-22 香港科技大学 Antifouling furan-2-one derivatives
CN104356730A (en) * 2014-10-27 2015-02-18 中国科学院南海海洋研究所 Application of class of butenolide compounds in preparation of marine biofouling prevention coating material

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Publication number Priority date Publication date Assignee Title
CN101541892A (en) * 2007-04-02 2009-09-23 釜山大学校产学协力团 Information processing device and method
CN101550305A (en) * 2008-04-02 2009-10-07 上海海悦涂料有限公司 Long-life self-polishing antifouling coating
CN102105542A (en) * 2008-07-24 2011-06-22 香港科技大学 Antifouling furan-2-one derivatives
CN104356730A (en) * 2014-10-27 2015-02-18 中国科学院南海海洋研究所 Application of class of butenolide compounds in preparation of marine biofouling prevention coating material

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111040087A (en) * 2019-12-31 2020-04-21 常州大学 Preparation method of self-polishing antifouling resin
CN111218187A (en) * 2020-03-06 2020-06-02 中国科学院宁波材料技术与工程研究所 Environment-friendly fluorine-silicon modified acrylic acid antifouling paint with micro-nano-like structure, and preparation method and application thereof
CN111218187B (en) * 2020-03-06 2022-02-11 中国科学院宁波材料技术与工程研究所 Environment-friendly fluorine-silicon modified acrylic acid antifouling paint with micro-nano-like structure, and preparation method and application thereof
CN115109449A (en) * 2021-03-18 2022-09-27 香港科技大学 Antifouling compound BOC-butenolide with potent ability to inhibit adhesion of marine invertebrate larvae
CN116240728A (en) * 2022-12-30 2023-06-09 佛山港科涂工技术有限公司 Water-based bionic environment-friendly antifouling paint and preparation method and application thereof
CN116240728B (en) * 2022-12-30 2024-01-16 佛山港科涂工技术有限公司 Water-based bionic environment-friendly antifouling paint and preparation method and application thereof

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Application publication date: 20170524