CN104877421A - Polyethyleneglycol-containing fluorinated polysiloxane modification acrylic acid antifouling paint and preparing method thereof - Google Patents
Polyethyleneglycol-containing fluorinated polysiloxane modification acrylic acid antifouling paint and preparing method thereof Download PDFInfo
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- CN104877421A CN104877421A CN201510315198.7A CN201510315198A CN104877421A CN 104877421 A CN104877421 A CN 104877421A CN 201510315198 A CN201510315198 A CN 201510315198A CN 104877421 A CN104877421 A CN 104877421A
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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
- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
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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
- 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
- C09D5/1675—Polyorganosiloxane-containing compositions
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- 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
- C08L2205/03—Polymer mixtures characterised by other features containing three or more polymers in a blend
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Abstract
The invention relates to a polyethyleneglycol-containing fluorinated polysiloxane modification acrylic acid antifouling paint and a preparing method of the paint. The paint consists of the following ingredients in percentage by weight: 84 to 96 percent of polyethyleneglycol-containing acrylic acid prepolymers, 2 to 14 percent of poly-dimethoxydimethylsilane oligomers and 2 to 14 percent of perfluoropolyether oligomers. The paint provided by the invention can be solidified into a film at the room temperature through polycondensation, the use is convenient, a heat source is not needed, the energy consumption is reduced, and in addition, the paint provided by the invention contains PEG (polyethylene glycol) chain segments with the protein-resistant and antibacterial characteristics, so that better anti-biological adhesion performance is realized.
Description
Technical field
The present invention relates to a kind of vinylformic acid antifouling paint and preparation method thereof, particularly a kind of fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol and preparation method thereof.
Background technology
Long-term submergence boats and ships in the seawater can be subject to halobiontic stained.When after boats and ships attachment marine organisms, surface friction drag can be caused to increase, reduce ship's speed, increase fuel consumption, and then cause unnecessary financial loss.Solve the method for marine biofouling many, wherein most effective means applies marine antifouling coating exactly.
Traditional marine antifouling coating falls behind, pollutes large and be eliminated action time short morning due to its technique.Although organotin is obvious from polishing class coating anti-fouling effect, organotin stable existence and accumulating in water, can cause some organisms deformities, also likely enter food chain, become potential safety hazard affect human health and ecology.Along with Marine Environmental Protection Committee's (MEPC) forbidding organotin-based paints, development environment friendly marine antifouling coating becomes inexorable trend.
In numerous environmentally friendly marine antifouling coating, the low surface energy coatings containing fluorine/silicon receives much concern.It combines the excellent properties of organosilicon coating and fluorocarbon coating, has that surface energy is low, Young's modulus is low, antifouling working lipe is long, a feature of nontoxic and good mechanical property.But this kind of coating is owing to cannot cut off the attachment of microorganism from root, its antibiont broad spectrum is lower.In order to improve biorefractive broad spectrum, need to cut off halobiontic attachment from root.The first step of marine organisms attachment is exactly the attachment of marine microorganism, and the key of this step is exactly protein and the combining of matrix.In order to reach antibacterial object, some structure with anti-microbial activity or functional groups can be introduced in matrix resin.Patent CN103788287 describes a kind of antibacterial modified low surface energy type marine antifouling coating resin.By organofluorine compound and the mode synthetic resins of quaternary ammonium salt by chemical bonding with germicidal action, this resin not only has lower surface energy, stoping the attachment of bacterium and microorganism by adding the quaternary ammonium salt with germicidal action, well having cut off halobiontic attachment from root.But quaternary ammonium salt still has certain toxicity, and easy adsorption activity negatively charged ion and losing efficacy.
There are some researches show, the coating containing polyoxyethylene glycol (PEG) group can show good anti-protein capability.PEG, can form one deck hydration layer at coatingsurface when contacting with water, thus block protein and contact with matrix phase, can cut off biodeterioration from root.Therefore, organic fluorinated silicone resin is combined with the PEG with anti-protein adsorption ability, antifouling coating not only can be made to obtain the advantages such as organic fluorinated silicone resin low surface energy, low elastic modulus and good mechanical property, its biorefractive broad spectrum can be improved again simultaneously.
Summary of the invention
One of the object of the invention is to provide a kind of fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol.
Two of object of the present invention is the preparation method providing this antifouling paint.
For achieving the above object, the present invention adopts following technical scheme:
Containing a fluorinated silicone modified vinylformic acid antifouling paint for polyoxyethylene glycol, it is characterized in that this system component and weight percentage are:
Containing the acrylic polymer 84 ~ 96% of polyoxyethylene glycol,
Poly-dimethoxysilane oligopolymer 2 ~ 14%,
PFPE oligopolymer 2 ~ 14%;
The weight percentage sum of above each component is 100%;
The described acrylic polymer containing polyoxyethylene glycol is the prepolymer formed through Raolical polymerizable by the mass ratio of 5:4:1 by butyl acrylate, methyl methacrylate and allyl polyglycol;
Described poly-dimethoxysilane oligopolymer is hydroxy silicon oil and the 3-isocyanate group propyl-triethoxysilicane mol ratio by 1:2 ~ 2.1, the oligopolymer formed under the effect of catalyst dibutyltin dilaurylate;
Described PFPE oligopolymer is two hydroxypropyl PFPE and the 3-isocyanate group propyl-triethoxysilicane mol ratio by 1:2 ~ 2.1, the oligopolymer formed under the effect of catalyst dibutyltin dilaurylate.
Above-mentioned allyl polyglycol, its number-average molecular weight scope is 1000-4000.
Above-mentioned hydroxy silicon oil number-average molecular weight scope is 1000-8000.
Above-mentioned two hydroxypropyl PFPE, its number-average molecular weight scope is 700-2000.
Prepare a method for the above-mentioned fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol, it is characterized in that the concrete steps of the method are:
A. butyl acrylate, methyl methacrylate and allyl polyglycol and azo-initiator are dissolved in the mixed solvent of dimethylbenzene and butylacetate, stir and be heated to 85 ° of C, insulation 2h; Add initiator subsequently, be warming up to 110 ° of C and react 2h, the obtained acrylic polymer containing polyoxyethylene glycol; Each raw material dosage scope is as follows:
Butyl acrylate 19 ~ 44%,
Methyl methacrylate 16 ~ 38%,
Allyl polyglycol 3 ~ 13%,
Initiator 0.15 ~ 3.5%,
The mass percentage sum of each raw material is 100% above;
B. hydroxy silicon oil and 3-isocyanate group propyl-triethoxysilicane are dissolved in tetrahydrofuran (THF) by the mol ratio of 1:2 ~ 2.1, add the dibutyl tin laurate of catalyst levels, stir and be heated to 65 ° of C, insulation 5h, obtained poly-dimethoxysilane oligopolymer;
C. two hydroxypropyl PFPE and 3-isocyanate group propyl-triethoxysilicane are dissolved in tetrahydrofuran (THF) by the mol ratio of 1:2 ~ 2.1, add the dibutyl tin laurate of catalyst levels, stir and be heated to 65 ° of C, insulation 2h, obtained PFPE oligopolymer;
D. step a, b and c gained are mixed containing the acrylic polymer of polyoxyethylene glycol, poly-dimethoxysilane oligopolymer and PFPE oligopolymer, make the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol.
Above-mentioned azo-initiator can select the one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl etc.
Fluorinated silicone modified vinylformic acid antifouling paint containing PEG of the present invention can also comprise color stuffing, and filler can select titanium dioxide, silicon-dioxide, talcum powder etc.; Pigment can select mineral dye and pigment dyestuff, as carbon black, iron oxide yellow etc.
PEG chain segment is incorporated in organic fluorinated silicone resin by the present invention, promotes the antifouling property of coating from root, and this coating is nontoxic, and duration of service is long, meets present environmental protection condition.Coating provided by the invention is at room temperature just by condensation curing film forming, easy to use, without the need to thermal source, reduces energy consumption, and the PEG chain segment containing anti-albumen, antimicrobial characteristic in coating provided by the invention, thus has good antibiont tack.
Accompanying drawing explanation
Fig. 1 is anti-bacteria test result and explanation.(a) blank glass sheet; (b) DC3140; C () singly organizes A; (d) embodiment 4; (e) embodiment 5; (f) embodiment 6; (g) embodiment 7; (h) embodiment 8.
Fig. 2 is anti-algae test result.The chlorophyll content of DC3140, BOH and embodiment 4-embodiment 8 coating sample.
Specific embodiment
Embodiment 1
Present embodiments provide the synthetic method containing PEG prepolymer A: 20 g dimethylbenzene and 20 g N-BUTYL ACETATEs are joined in the there-necked flask that agitator, constant voltage separating funnel, reflux exchanger are housed, be warming up to 85 ° of C.After taking 20 g dimethylbenzene, 20 g N-BUTYL ACETATEs, 1.6 g AIBN, 50 g butyl acrylates, 40 g methyl methacrylates, 10 g allyl polyglycol mixed dissolutions, slowly instill in there-necked flask in 1.5 h, dropwise follow-up continuation of insurance temperature 2 h.Be warming up to 110 ° of C, then after taking 0.4 g AIBN, 20 g dimethylbenzene, 20 g N-BUTYL ACETATE mixed dissolutions respectively, slowly instill in there-necked flask in 0.5 h, dropwise follow-up continuation of insurance temperature 2 h.Cooling discharge, obtains the hydroxyl acrylic prepolymer A containing PEG, in white emulsion state.
Embodiment 2
Present embodiments provide the synthetic method of poly-dimethoxysilane oligopolymer B: join in the there-necked flask that agitator, constant pressure funnel, reflux exchanger are housed by 15.1870 g tetrahydrofuran (THF)s and 15.0000 g hydroxy silicon oils, oil bath pan is warming up to 65 ° of C.After taking 5.1870 g 3-isocyanate group propyl-triethoxysilicanes, 0.0063 g dibutyl tin laurate mixed dissolution again, slowly be added dropwise to vigorous stirring in there-necked flask, dropwise follow-up continuation of insurance temperature 5 h, cooling discharge obtains α, the polydimethylsiloxane oligopolymer B of ω-triethoxyl silane end-blocking, in water white transparency oily.
Embodiment 3
Present embodiments provide the synthetic method of PFPE oligopolymer C: join in the there-necked flask that agitator, constant pressure funnel, reflux exchanger are housed by 12.6870 g tetrahydrofuran (THF)s and the two hydroxypropyl PFPE of 7.5000 g, oil bath pan is warming up to 65 ° of C.After taking 5.1870 g 3-isocyanate group propyl-triethoxysilicanes, 0.0063 g dibutyl tin laurate mixed dissolution again, slowly be added dropwise in there-necked flask in 10 minutes with vigorous stirring, dropwise follow-up continuation of insurance temperature 2 h, cooling discharge obtains, the PFPE oligopolymer of-triethoxyl silane end-blocking is denoted as PFU, in pale yellow transparent oily.
Embodiment 4-embodiment 8
Take the A of different mass, B, component C dissolve after mixing, stir 2h, then by gained resin-coating on the slide glass processed.Each component proportion following (table 1):
The each embodiment component proportion of table 1
Embodiment 9
Contact angle and surface energy are tested: by coated sample hold over night in close drying space, thermofixation 6 h in the baking oven every other day under 90 ° of C.The sample handled well selects water and methylene iodide to test contact angle respectively, and gauging surface energy, the direct cured product of this process commercialization silicone resin DC3140 and component A is as reference.Acquired results is in table 2:
Table 2 embodiment contact angle and surface energy
Embodiment 10
Young's modulus characterizes: Young's modulus adopts in-situ nano mechanical test instrument to levy, and acquired results is in table 3.Fouling organism desorption power after attachment is subject to coating elastic modulus E and surface energy γ c joint effect, with (E γ c)
1/2proportional, i.e. (E γ c)
1/2be worth less, fouling organism is more difficult to be attached on low surface energy antifouling coating.
Table 3 embodiment Young's modulus
See Fig. 1, be anti-bacteria test result figure.Antibacterial test adopts intestinal bacteria to test, the sample be coated on slide glass is immersed in intestinal bacteria suspension, take out after 24h and clean, then with crystal violet solution, intestinal bacteria being dyeed, the sample microscopic examination bacterial adhesion situation processed.
See Fig. 2, algae-resistant is adhered to experiment and is adopted boat-shaped diatom Navicula to test, and boat-shaped diatom is at 25 ° of C, and illumination condition is cultivate 20 days under 2000 Lux, and with artificial seawater, (dilution acquisition diatom concentration is that the algae liquid of 1 × 104cells mL-1 is for subsequent use.Coating sample soaks two days in artificial seawater, then take out and be placed in culture dish respectively, the algae liquid respectively getting 30 ml 1 × 104cells mL-1 joins in culture dish, coating sample is immersed in algae liquid and cultivates 8 days in being placed in illumination box (25 ° of C, illumination condition is 2000 Lux).Afterwards by coating sample taking-up artificial seawater repeatedly rinsing wash away the diatom do not adhered to completely, dry rear 5 mL acetone of respectively getting and soak and be attached with the coating sample of diatom, extract diatom chlorophyll.Extracting solution adopts twin-beam ultraviolet spectrophotometer to characterize, and calculates chlorophyll content.
Can be found out by above result and antibacterial and anti-algae experimental result accompanying drawing, embodiment 4-embodiment 8 surface energy is lower, close to commercialization organosilicon DC3140; Modular ratio DC3140 is less, is beneficial to fouling organism desorption; Antibacterial and the anti-algae effect of embodiment 4-embodiment 8 is all better than DC3140.
As described in the above embodiment the present invention, other adopting method same or analogous with it and component to obtain have parents' marine antifouling coating of biological resistance, all in scope.
Claims (6)
1., containing a fluorinated silicone modified vinylformic acid antifouling paint for polyoxyethylene glycol, it is characterized in that this system component and weight percentage are:
Containing the acrylic polymer 84 ~ 96% of polyoxyethylene glycol,
Poly-dimethoxysilane oligopolymer 2 ~ 14%,
PFPE oligopolymer 2 ~ 14%;
The weight percentage sum of above each component is 100%;
The described acrylic polymer containing polyoxyethylene glycol is the prepolymer formed through Raolical polymerizable by the mass ratio of 5:4:1 by butyl acrylate, methyl methacrylate and allyl polyglycol;
Described poly-dimethoxysilane oligopolymer is hydroxy silicon oil and the 3-isocyanate group propyl-triethoxysilicane mol ratio by 1:2 ~ 2.1, the oligopolymer formed under the effect of catalyst dibutyltin dilaurylate;
Described PFPE oligopolymer is two hydroxypropyl PFPE and the 3-isocyanate group propyl-triethoxysilicane mol ratio by 1:2 ~ 2.1, the oligopolymer formed under the effect of catalyst dibutyltin dilaurylate.
2. the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol according to claim 1, it is characterized in that described allyl polyglycol, its number-average molecular weight is 1000-4000.
3. the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol according to claim 1, is characterized in that described hydroxy silicon oil number-average molecular weight is 1000-8000.
4. the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol according to claim 1, it is characterized in that described two hydroxypropyl PFPE, its number-average molecular weight is 700-2000.
5. prepare a method for the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol according to any one of claim 1 to 4, it is characterized in that the concrete steps of the method are:
A. butyl acrylate, methyl methacrylate and allyl polyglycol and azo-initiator are dissolved in the mixed solvent of dimethylbenzene and butylacetate, stir and be heated to 85 ° of C, insulation 2h; Add initiator subsequently, be warming up to 110 ° of C and react 2h, the obtained acrylic polymer containing polyoxyethylene glycol; Each raw material dosage scope is as follows:
Butyl acrylate 19 ~ 44%,
Methyl methacrylate 16 ~ 38%,
Allyl polyglycol 3 ~ 13%,
Initiator 0.15 ~ 3.5%,
The mass percentage sum of each raw material is 100% above;
B. hydroxy silicon oil and 3-isocyanate group propyl-triethoxysilicane are dissolved in tetrahydrofuran (THF) by the mol ratio of 1:2 ~ 2.1, add the dibutyl tin laurate of catalyst levels, stir and be heated to 65 ° of C, insulation 5h, obtained poly-dimethoxysilane oligopolymer;
C. two hydroxypropyl PFPE and 3-isocyanate group propyl-triethoxysilicane are dissolved in tetrahydrofuran (THF) by the mol ratio of 1:2 ~ 2.1, add the dibutyl tin laurate of catalyst levels, stir and be heated to 65 ° of C, insulation 2h, obtained PFPE oligopolymer;
D. step a, b and c gained are mixed containing the acrylic polymer of polyoxyethylene glycol, poly-dimethoxysilane oligopolymer and PFPE oligopolymer, make the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol.
6. the preparation method of the fluorinated silicone modified vinylformic acid antifouling paint containing polyoxyethylene glycol according to claim 2, is characterized in that described azo-initiator can select the one in Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), 2,2'-Azobis(2,4-dimethylvaleronitrile), azo-bis-iso-dimethyl etc.
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Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107298751A (en) * | 2016-04-15 | 2017-10-27 | 信越化学工业株式会社 | Fluorine-containing system: compositions and its manufacture method, fluorine-containing active energy ray-curable composition and article |
| CN107955524A (en) * | 2017-11-22 | 2018-04-24 | 上海大学 | Organic silicon antifouling paint of the quaternary ammonium salt containing PEG/ and preparation method thereof |
| CN108148204A (en) * | 2017-12-21 | 2018-06-12 | 广东顺德墨赛生物科技有限公司 | Perfluoropolyether-polyethylene glycol blocked copolymer, preparation method and applications |
| CN109517132A (en) * | 2017-09-19 | 2019-03-26 | 中昊晨光化工研究院有限公司 | A kind of compound and preparation method thereof with anti-pollution |
| CN109593422A (en) * | 2018-10-10 | 2019-04-09 | 中山大学 | A kind of water-soluble low surface energy marine antifouling coating |
| CN110218519A (en) * | 2019-05-09 | 2019-09-10 | 华南理工大学 | A kind of static state anti-pollution self demixing organosilicon coating and the preparation method and application thereof |
| CN116535972A (en) * | 2023-06-14 | 2023-08-04 | 哈尔滨工程大学 | Dual-functional organosilicon-acrylate antifouling paint, antifouling coating, preparation method and application thereof |
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Cited By (12)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN107298751A (en) * | 2016-04-15 | 2017-10-27 | 信越化学工业株式会社 | Fluorine-containing system: compositions and its manufacture method, fluorine-containing active energy ray-curable composition and article |
| CN107298751B (en) * | 2016-04-15 | 2021-10-26 | 信越化学工业株式会社 | Fluorine-containing acrylic composition, method for producing same, fluorine-containing active energy ray-curable composition, and article |
| CN109517132A (en) * | 2017-09-19 | 2019-03-26 | 中昊晨光化工研究院有限公司 | A kind of compound and preparation method thereof with anti-pollution |
| CN109517132B (en) * | 2017-09-19 | 2020-05-01 | 中昊晨光化工研究院有限公司 | Compound with anti-pollution effect and preparation method thereof |
| CN107955524A (en) * | 2017-11-22 | 2018-04-24 | 上海大学 | Organic silicon antifouling paint of the quaternary ammonium salt containing PEG/ and preparation method thereof |
| CN108148204A (en) * | 2017-12-21 | 2018-06-12 | 广东顺德墨赛生物科技有限公司 | Perfluoropolyether-polyethylene glycol blocked copolymer, preparation method and applications |
| CN108148204B (en) * | 2017-12-21 | 2020-10-20 | 广东永诺医疗科技有限公司 | Perfluoropolyether-polyethylene glycol block copolymer, preparation method and application thereof |
| CN109593422A (en) * | 2018-10-10 | 2019-04-09 | 中山大学 | A kind of water-soluble low surface energy marine antifouling coating |
| CN110218519A (en) * | 2019-05-09 | 2019-09-10 | 华南理工大学 | A kind of static state anti-pollution self demixing organosilicon coating and the preparation method and application thereof |
| CN110218519B (en) * | 2019-05-09 | 2020-04-28 | 华南理工大学 | Static anti-fouling self-layering organic silicon coating and preparation method and application thereof |
| CN116535972A (en) * | 2023-06-14 | 2023-08-04 | 哈尔滨工程大学 | Dual-functional organosilicon-acrylate antifouling paint, antifouling coating, preparation method and application thereof |
| CN116535972B (en) * | 2023-06-14 | 2024-03-29 | 哈尔滨工程大学 | Dual-functional organosilicon-acrylate antifouling paint, antifouling coating, preparation method and application thereof |
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Application publication date: 20150902 |