CN115595029A - Amphoteric ion-based environment-friendly marine antifouling paint and preparation method thereof - Google Patents
Amphoteric ion-based environment-friendly marine antifouling paint and preparation method thereof Download PDFInfo
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- CN115595029A CN115595029A CN202211282337.7A CN202211282337A CN115595029A CN 115595029 A CN115595029 A CN 115595029A CN 202211282337 A CN202211282337 A CN 202211282337A CN 115595029 A CN115595029 A CN 115595029A
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- antifouling
- coating
- zwitterionic
- antifouling paint
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- 230000003373 anti-fouling effect Effects 0.000 title claims abstract description 88
- 239000003973 paint Substances 0.000 title claims abstract description 39
- 238000002360 preparation method Methods 0.000 title description 7
- 238000000576 coating method Methods 0.000 claims abstract description 56
- 239000011248 coating agent Substances 0.000 claims abstract description 49
- 230000000844 anti-bacterial effect Effects 0.000 claims abstract description 20
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229920000178 Acrylic resin Polymers 0.000 claims abstract description 16
- 239000004925 Acrylic resin Substances 0.000 claims abstract description 16
- 239000002904 solvent Substances 0.000 claims abstract description 13
- 239000002243 precursor Substances 0.000 claims abstract description 11
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012752 auxiliary agent Substances 0.000 claims abstract description 8
- 239000003899 bactericide agent Substances 0.000 claims abstract description 8
- 238000000034 method Methods 0.000 claims abstract description 8
- 239000006185 dispersion Substances 0.000 claims description 15
- -1 siloxanes Chemical class 0.000 claims description 15
- 125000005369 trialkoxysilyl group Chemical group 0.000 claims description 10
- 150000002500 ions Chemical class 0.000 claims description 9
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 8
- 229910052710 silicon Inorganic materials 0.000 claims description 8
- 239000010703 silicon Substances 0.000 claims description 8
- 239000008096 xylene Substances 0.000 claims description 8
- 238000001723 curing Methods 0.000 claims description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 238000010008 shearing Methods 0.000 claims description 5
- 239000000080 wetting agent Substances 0.000 claims description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 claims description 4
- 229910010413 TiO 2 Inorganic materials 0.000 claims description 4
- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 claims description 4
- 238000004132 cross linking Methods 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- 230000007062 hydrolysis Effects 0.000 claims description 4
- 238000006460 hydrolysis reaction Methods 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 238000003756 stirring Methods 0.000 claims description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 claims description 2
- 229910002808 Si–O–Si Inorganic materials 0.000 claims description 2
- 239000002518 antifoaming agent Substances 0.000 claims description 2
- 238000009833 condensation Methods 0.000 claims description 2
- 230000005494 condensation Effects 0.000 claims description 2
- 239000000417 fungicide Substances 0.000 claims description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 2
- 238000013008 moisture curing Methods 0.000 claims description 2
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 2
- LLHKCFNBLRBOGN-UHFFFAOYSA-N propylene glycol methyl ether acetate Chemical compound COCC(C)OC(C)=O LLHKCFNBLRBOGN-UHFFFAOYSA-N 0.000 claims description 2
- 239000002519 antifouling agent Substances 0.000 abstract description 16
- 239000013535 sea water Substances 0.000 abstract description 7
- 238000004140 cleaning Methods 0.000 abstract description 4
- 238000011065 in-situ storage Methods 0.000 abstract description 3
- 239000000126 substance Substances 0.000 abstract description 3
- 239000003242 anti bacterial agent Substances 0.000 abstract description 2
- 238000003889 chemical engineering Methods 0.000 abstract description 2
- 229920001688 coating polymer Polymers 0.000 abstract description 2
- 239000012847 fine chemical Substances 0.000 abstract description 2
- 230000002035 prolonged effect Effects 0.000 abstract description 2
- 239000011521 glass Substances 0.000 description 40
- 230000001580 bacterial effect Effects 0.000 description 14
- 239000011347 resin Substances 0.000 description 12
- 229920005989 resin Polymers 0.000 description 12
- 239000007788 liquid Substances 0.000 description 11
- 239000002105 nanoparticle Substances 0.000 description 10
- 241000237852 Mollusca Species 0.000 description 7
- 230000000366 juvenile effect Effects 0.000 description 7
- 239000011324 bead Substances 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 238000005498 polishing Methods 0.000 description 5
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 4
- 238000000227 grinding Methods 0.000 description 4
- 239000012528 membrane Substances 0.000 description 4
- UBWPFVBWNNQIQD-UHFFFAOYSA-N CO[Si](CCCOCC(CN1SC(C=CC=C2)=C2C1=O)O)(OC)OC Chemical compound CO[Si](CCCOCC(CN1SC(C=CC=C2)=C2C1=O)O)(OC)OC UBWPFVBWNNQIQD-UHFFFAOYSA-N 0.000 description 3
- 239000003082 abrasive agent Substances 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 231100000252 nontoxic Toxicity 0.000 description 3
- 230000003000 nontoxic effect Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 2
- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000010521 absorption reaction Methods 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- 229960003237 betaine Drugs 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 239000011664 nicotinic acid Substances 0.000 description 2
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 description 2
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 2
- 229920001483 poly(ethyl methacrylate) polymer Polymers 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- FSSPGSAQUIYDCN-UHFFFAOYSA-N 1,3-Propane sultone Chemical compound O=S1(=O)CCCO1 FSSPGSAQUIYDCN-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- KSCAZPYHLGGNPZ-UHFFFAOYSA-N 3-chloropropyl(triethoxy)silane Chemical compound CCO[Si](OCC)(OCC)CCCCl KSCAZPYHLGGNPZ-UHFFFAOYSA-N 0.000 description 1
- RWLDCNACDPTRMY-UHFFFAOYSA-N 3-triethoxysilyl-n-(3-triethoxysilylpropyl)propan-1-amine Chemical compound CCO[Si](OCC)(OCC)CCCNCCC[Si](OCC)(OCC)OCC RWLDCNACDPTRMY-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-UHFFFAOYSA-N 0.000 description 1
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 238000005576 amination reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000013530 defoamer Substances 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- NKSJNEHGWDZZQF-UHFFFAOYSA-N ethenyl(trimethoxy)silane Chemical compound CO[Si](OC)(OC)C=C NKSJNEHGWDZZQF-UHFFFAOYSA-N 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 229920001477 hydrophilic polymer Polymers 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000002401 inhibitory effect Effects 0.000 description 1
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 238000002464 physical blending Methods 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000010069 protein adhesion Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- PZJJKWKADRNWSW-UHFFFAOYSA-N trimethoxysilicon Chemical group CO[Si](OC)OC PZJJKWKADRNWSW-UHFFFAOYSA-N 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
-
- 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
- C09D5/1618—Non-macromolecular compounds inorganic
-
- 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
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
- C09D5/1668—Vinyl-type polymers
-
- 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
- C09D5/1687—Use of special additives
-
- 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
- C08K3/02—Elements
- C08K3/08—Metals
- C08K2003/0806—Silver
-
- 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
- C08K2003/2237—Oxides; Hydroxides of metals of titanium
- C08K2003/2241—Titanium dioxide
-
- 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
- C08K2003/2296—Oxides; Hydroxides of metals of zinc
Abstract
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a zwitterionic environment-friendly marine antifouling paint. The coating comprises the following components in parts by weight: 40-80 parts of moisture-curable acrylic resin, 5-30 parts of zwitterionic precursor siloxane, 2-20 parts of antifouling antibacterial siloxane, 2-50 parts of inorganic nano bactericide, 0-8 parts of aminosilane, 5-20 parts of solvent and 0-5 parts of auxiliary agent. The organic antifouling agent in the coating is chemically bonded in a coating polymer chain in the curing process and becomes a part of a film-forming substance, so that the service life of the antifouling agent is prolonged; the zwitterion precursor siloxane generates zwitterions in situ, and the zwitterions and the organic antifouling agent and/or the inorganic nano antibacterial agent synergistically act to improve the antifouling performance of the coating. The coating can be sprayed and cured at room temperature in a large scale, has high underwater mechanical strength, can be suitable for antifouling coatings of ships, seawater pipelines and other occasions, and is particularly suitable for being used as a hard antifouling coating for cleaning an underwater intelligent robot.
Description
Technical Field
The invention belongs to the technical field of fine chemical engineering, and particularly relates to a marine antifouling paint and a preparation method thereof.
Background
Currently, there are two main types of film-forming resins for commercial marine antifouling coatings: self-polishing resins (mainly acrylic silicone resins) and silicone resins. Acrylic siloxane resinThe hydrolysis of trialkoxysilyl under the condition of weak alkali in seawater generates carboxyl, the hydrophilicity of polymer molecules is increased, the coating enters seawater under the washing of water flow, the diffusion distance of an antifouling agent in the coating to a coating/seawater interface is shortened, and the coating is ensured to keep a certain bactericide concentration for a long time close to the surface, so that the antifouling effect is achieved. However, cu is commonly used in such coatings 2 The content of the O antifouling agent is high, the environmental friendliness is poor, the self-polishing resin can be gradually lost in the using process, and the service life of the self-polishing resin is greatly different in different service environments. The marine antifouling coating based on the organic silicon resin is a fouling release type coating, and as the surface energy of the coating is low, the adhesion force of fouling organisms on the surface of the coating is low, macroscopic fouling organisms can be automatically removed at a certain navigational speed. Although the organic silicon resin antifouling coating is environment-friendly and good, the organic silicon resin antifouling coating has poor static antifouling performance, weak mechanical property and poor recoatability, and limits the application range of the organic silicon resin antifouling coating. Therefore, the development of novel environment-friendly marine antifouling paint is urgently needed.
Currently, the main directions of environmentally friendly marine antifouling paints include: (1) Hydrophilic components such as hydrophilic polymers, zwitterions and the like are introduced into the coating in the hydrophilization direction, the adhesion of macroscopic organisms is reduced mainly by inhibiting the formation of a conditioned membrane and a biological membrane, but the underwater mechanical property of the coating is seriously deteriorated due to too much introduced hydrophilic groups, and the generation of a workpiece membrane and the biological membrane cannot be effectively inhibited due to too few hydrophilic groups; (2) The direction of the nontoxic antifouling agent comprises the application of natural antifouling agents and artificially synthesized nontoxic antifouling agents, but the antifouling agents are quickly released in seawater, are easy to degrade and have short antifouling life; (3) The bionic micro-nano structure surface is antifouling, but the antifouling surface is not easy to prepare in large scale, is easy to wear and is difficult to regenerate. Therefore, the currently reported environmentally friendly marine antifouling coatings face difficulties in practical application.
In the development direction of the environment-friendly marine antifouling paint, the introduction of zwitterions is concerned, the zwitterions have strong hydrophilic capability, easily form high hydrophilicity on the surface or form an amphiphilic surface with a hydrophobic chain segment, have good protein adhesion resistance, and are bionic antifouling groups. The use of zwitterions for the preparation of marine antifouling coatings has been reported: for example, chinese patent CN 2015108299158 reports a betaine-containing zwitterionic modified acrylate self-polishing antifouling paint and a preparation method thereof, and the composition of the paint comprises betaine-containing zwitterionic functionalized acrylic acid self-polishing resin, a composite antifouling agent, a pigment filler, an auxiliary agent and the like. In the invention patent 201711477882.0, a copolymer containing tetravinyl pyridine is synthesized, and then the copolymer reacts with propane sultone to obtain the zwitterion antifouling paint resin. According to the Chinese invention patent 201410680546.6, the quaternary amination reaction is carried out on methoxy polyethylene glycol-b-polyethyl methacrylate dimethyl sulfopropyl betaine-b-polyethyl methacrylate and 3-chloropropyl triethoxysilane, so as to prepare the antifouling and antibacterial coating material containing zwitterions. The invention patent 202080005838.3 in China adopts bis [3- (triethoxysilyl) propyl ] amine to react with a zwitterion monomer to generate a silane coupling agent with zwitterion, and then the silane coupling agent reacts with polyethylene glycol double-end-capped PDMS and hydroxyl end-capped PDMS to prepare the silica gel antifouling paint containing zwitterion. Most of zwitterions in the antifouling paint are introduced by a pre-synthesized zwitterion-containing copolymer, the content of the zwitterions is fixed, the corresponding coating has high water absorption and poor underwater mechanical property; or the amphoteric ion is not enough to be matched with other antifouling agents, and the antifouling performance in the actual ocean cannot meet the use requirement. The antifouling paint is an effective way for improving the antifouling performance of the environment-friendly marine antifouling paint through the compound synergistic effect of the antifouling paint and a nontoxic organic or inorganic antifouling agent, but the antifouling life cannot meet the practical application. The combination of the environment-friendly marine antifouling paint and the underwater intelligent robot cleaning is an ideal method for solving the practical marine application of the paint. However, the coating suitable for cleaning the underwater robot generally needs higher mechanical strength, and the existing resin system for the antifouling coating does not meet the use requirement. Therefore, the amphoteric ion-based environment-friendly marine antifouling coating with excellent antifouling performance and outstanding underwater mechanical performance needs to be further developed.
Disclosure of Invention
The invention aims to provide a zwitter-ion-based environment-friendly marine antifouling paint with good underwater mechanical property, strong antifouling function and long antifouling life and a preparation method thereof.
The invention provides a zwitterionic environment-friendly marine antifouling paint which comprises the following specific components in parts by weight:
moisture curable acrylic resin: 40-80;
zwitterionic precursor siloxanes: 5-30;
organic antifouling antibacterial siloxane: 2-20;
inorganic nano-fungicide: 2 to 50;
amino silane: 0 to 8;
solvent: 5-20;
auxiliary agent: 0-5.
In the amphoteric ion-based environment-friendly marine antifouling paint, the groups for crosslinking in the moisture-curable acrylic resin are trialkoxysilyl groups. The group generates silicon hydroxyl through hydrolysis, and then Si-O-Si bonds are formed through condensation among the silicon hydroxyl, so that the room-temperature curing crosslinking of the coating is realized.
Further, trialkoxysilyl of the moisture-curable acrylic resin is trimethoxysilyl or triethoxysilyl.
Further, the moisture-curable acrylic resin may be derived from a commercially available product such as 818A resin (solids content 68%, viscosity 1300mPa. S, solvent: xylene) from Shanghai Huarong company; it can also be prepared by free radical copolymerization of methyl methacrylate, butyl acrylate, styrene, methacryloxypropyltrimethoxysilane (or vinyltrimethoxysilane) and other monomers.
In the zwitterion-based environment-friendly marine antifouling paint, the zwitterion precursor siloxane is one of (N-triisopropylsilylacylpropyl) -3-aminopropyltrialkoxysilane, (N-methoxyacylethyl) -3-aminopropyltrialkoxysilane and bis (N-methoxyacylethyl) -3-aminopropyltrialkoxysilane; the zwitterion is generated by in-situ hydrolysis in the coating curing or using process and is mainly limited to the surface layer of the coating, so that high water absorption in the coating is avoided, and underwater high mechanical property of the coating is facilitated to be obtained. Meanwhile, the zwitter-ion precursor siloxane can play the functions of a catalyst and a curing agent and promote the coating to be cured and formed into a film.
In the zwitterionic environment-friendly marine antifouling paint, the organic antifouling antibacterial siloxane is at least one of 2- (2-hydroxy-3- (3- (trialkoxysilyl) propoxy) propyl) benzisothiazolin-3-one and 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (trialkoxysilyl) propyl) aniline.
In the zwitterionic environment-friendly marine antifouling paint, trialkoxy groups in the zwitterionic precursor siloxane and the organic antifouling antibacterial siloxane are one of trimethoxy groups or triethoxy groups.
Further, the antibacterial antifouling siloxane disclosed by the invention can be synthesized by adopting an organic synthesis method. Typically, for example, a siloxane containing 1, 2-benzisothiazolin-3-one antibacterial group is obtained by reacting 1, 2-benzisothiazolin-3-one with 3-glycidyloxypropyltrimethoxysilane under the following conditions: anhydrous environment, temperature 70 ℃ and time 40 h.
Furthermore, the antibacterial antifouling siloxane disclosed by the invention contains trialkoxysilyl, can react with moisture-cured acrylic resin in a film forming process, is chemically bonded into a film forming substance network, and avoids the problem of quick release caused by simple physical blending.
In the environment-friendly marine antifouling paint containing zwitterion group, the inorganic nano bactericide is selected from nano ZnO and nano Cu 2 O, nano TiO 2 And/or nano Ag.
In the environment-friendly marine antifouling paint containing the zwitterion group, the auxiliary agent comprises a leveling agent for the paint, a wetting agent and a defoaming agent.
In the amphoteric ion-based environment-friendly marine antifouling paint, the solvent is selected from one of butyl acetate, ethyl acetate, xylene, cyclohexanone and propylene glycol methyl ether acetate.
The invention also provides a preparation method of the amphoteric ion-based environment-friendly marine antifouling paint, which comprises the following specific steps:
firstly, adding the inorganic nano bactericide into the moisture-curing acrylic resin, and carrying out high-speed shearing dispersion or sanding; after the inorganic nano bactericide is dispersed, sequentially adding the organic antifouling antibacterial siloxane, the zwitter ion precursor siloxane, the solvent, the aminosilane and the auxiliary agent, stirring and dispersing for 0.5-1.0 hour to obtain the required coating.
The aminosilane and the auxiliary agent are mainly used for adjusting the curing speed of the coating and the appearance of the coating film, and can be added or not added according to actual conditions.
In the coating composition, the organic antifouling agent is chemically bonded in a coating polymer chain in a curing process to form a part of a film-forming substance, so that the service life of the antifouling agent is prolonged; meanwhile, zwitterion precursor siloxane generates zwitterion in situ, and the zwitterion and the organic antifouling agent and/or the inorganic nano antibacterial agent have synergistic effect to improve the antifouling performance of the coating. The coating can be sprayed and cured at room temperature in a large scale, the type and the using amount of the antifouling agent are convenient to regulate and control, the underwater mechanical strength is high, the pencil hardness is still kept above 1H after the coating is soaked in artificial seawater for nine months, and the coating has excellent antifouling performance.
Specifically, the bacterial load of the coating is reduced by 90-98% compared with that of a blank glass sheet in various antifouling tests in a laboratory; the diatom amount is reduced by 86-99% compared with that of the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 84-97% compared with that of a blank glass sheet; the diatom amount is reduced by 72-92% compared with that of the blank glass sheet; the adhesion amount of the juvenile mollusks is reduced by 82 to 95 percent compared with that of the blank glass sheet. In various antifouling tests in a laboratory, the bacterial load of the better group of coatings is reduced by 98 percent compared with that of a blank glass sheet; the diatom content was reduced by 99% compared to the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 97 percent compared with that of a blank glass sheet; the diatom amount is reduced by 92 percent compared with that of a blank glass sheet; the adhering amount of the juvenile mollusks is reduced by 95 percent compared with that of a blank glass sheet.
The amphoteric ion-based environment-friendly marine antifouling paint disclosed by the invention can be suitable for antifouling coatings of ships, seawater pipelines and other occasions, and is particularly suitable for being used as a hard antifouling coating for cleaning an underwater intelligent robot.
Detailed Description
The invention is further described below by means of specific examples.
Example 1:
30g of nano ZnO, 50g of moisture-curable acrylic resin 818A and 5g of solvent xylene are added into a plastic container, and glass beads are taken as abrasive materials to carry out high-speed shearing dispersion, so as to obtain stable nanoparticle dispersion liquid.
The nanoparticle dispersion, 10g of (N-methoxyacylethyl) -3-aminopropyltriethoxysilane, 3g of 2- (2-hydroxy-3- (3- (trimethoxysilyl) propoxy) propyl) benzisothiazolin-3-one, 2g of aminosilane were mixed, stirred at room temperature to give a homogeneous liquid, which was coated and cured at room temperature for 2 d.
In various antifouling tests of the coating in a laboratory, the bacterial content is reduced by 95 percent compared with that of a blank glass sheet; the diatom content is reduced by 92% compared with that of blank glass sheets. In various antifouling tests in the real sea, the bacterial load is reduced by 86 percent compared with that of a blank glass sheet; the diatom amount is reduced by 88% compared with that of the blank glass sheet; the adhering amount of the juvenile mollusks is reduced by 90 percent compared with that of a blank glass sheet.
Example 2:
5g of nano Cu 2 O, 5g of nano TiO 2 42g of moisture-curable acrylic resin 818A and 11g of xylene solvent are added into a plastic container, and glass beads are used as grinding materials for grinding and dispersing to obtain stable nanoparticle dispersion liquid.
Mixing the nanoparticle dispersion, 25g of (N-triisopropylsilylacylpropyl) -3-aminopropyltrimethoxysilane, 10g of 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (triethoxysilyl) propyl) aniline, 1g of a leveling agent and 1g of a wetting agent, stirring at room temperature to obtain a uniform liquid, and curing at room temperature for 2 d after coating.
In various antifouling tests of a laboratory, the bacterial content of the coating is reduced by 93 percent compared with that of a blank glass sheet; the diatom content was reduced by 86% compared to the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 90 percent compared with that of a blank glass sheet; the diatom amount is reduced by 76% compared with that of the blank glass sheet; the adhering amount of the juvenile mollusks is reduced by 82 percent compared with that of a blank glass sheet.
Example 3:
20g of nano ZnO, 10g of nano Ag, 40g of moisture-curable acrylic resin 818A and 6g of solvent xylene are added into a plastic container, and glass beads are used as abrasive materials for grinding and dispersing to obtain stable nanoparticle dispersion liquid.
The nanoparticle dispersion, 12g of bis (N-methoxyacylethyl) -3-aminopropyltriethoxysilane, 5g of 2- (2-hydroxy-3- (3- (triethoxysilyl) propoxy) propyl) benzisothiazolin-3-one, 3g of 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (trimethoxysilyl) propyl) aniline, 2g of aminosilane, 1g of leveling agent and 1g of defoamer were mixed, stirred at room temperature to obtain a uniform liquid, and cured at room temperature for 2 d after coating.
In various antifouling tests of the coating in a laboratory, the bacterial content is reduced by 96 percent compared with that of a blank glass sheet; the diatom content was 91% lower than that of the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 84 percent compared with that of a blank glass sheet; the diatom content is reduced by 72 percent compared with that of a blank glass sheet; the adhesion amount of the juvenile mollusks is reduced by 89 percent compared with that of a blank glass sheet.
Example 4:
10g of nano ZnO and 2g of nano Cu 2 O, 2g of nano Ag, 60g of moisture-curable acrylic resin 818A and 8g of solvent xylene are added into a plastic container, and glass beads are used as grinding materials to carry out high-speed shearing dispersion to obtain stable nanoparticle dispersion liquid.
The nanoparticle dispersion liquid, 8g of (N-triisopropylsilylacylpropyl) -3-aminopropyltrimethoxysilane, 5g of 2- (2-hydroxy-3- (3- (trimethoxysilyl) propoxy) propyl) benzisothiazolin-3-one, 4g of 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (triethoxysilyl) propyl) aniline, and 1g of a wetting agent were mixed, stirred at room temperature to obtain a uniform liquid, and cured at room temperature for 2 d after coating.
In various antifouling tests of a laboratory, the bacterial load of the coating is reduced by 95 percent compared with that of a blank glass sheet; the diatom content was 91% lower than that of the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 84 percent compared with that of a blank glass sheet; the diatom amount is reduced by 86 percent compared with that of the blank glass sheet; the adhering amount of the juvenile mollusks is reduced by 91 percent compared with that of a blank glass sheet.
Example 5:
5g of nano ZnO and 5g of nano Cu 2 O, 5g of nano TiO 2 5g of nano Ag, 50g of moisture-curable acrylic resin 818A and 10g of solvent xylene are added into a plastic container, and glass beads are taken as abrasive materials to carry out high-speed shearing dispersion to obtain stable nanoparticle dispersion liquid.
The nanoparticle dispersion, 10g of (N-methoxyacylethyl) -3-aminopropyltrimethoxysilane, 3g of 2- (2-hydroxy-3- (3- (trimethoxysilyl) propoxy) propyl) benzisothiazolin-3-one, 3g of 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (triethoxysilyl) propyl) aniline, 2g of aminosilane, 1g of wetting agent and 1g of leveling agent were mixed, stirred at room temperature to give a homogeneous liquid, which was cured at room temperature for 2 d after coating.
In various antifouling tests of a laboratory, the bacterial content of the coating is reduced by 98 percent compared with that of a blank glass sheet; the diatom content was reduced by 99% compared to the blank glass sheet. In various antifouling tests in the real sea, the bacterial load is reduced by 97 percent compared with that of a blank glass sheet; the diatom content is reduced by 92 percent compared with that of a blank glass sheet; the adhesion amount of the juvenile mollusks is reduced by 95 percent compared with that of a blank glass sheet.
Claims (9)
1. The environment-friendly marine antifouling paint containing the zwitterion group is characterized by comprising the following components in parts by weight:
moisture curable acrylic resin: 40-80;
zwitterionic precursor siloxanes: 5-30;
organic antifouling antibacterial siloxane: 2-20;
inorganic nano-fungicide: 2 to 50;
amino silane: 0 to 8;
solvent: 5-20;
auxiliary agent: 0-5.
2. The zwitterionic-based environment-friendly marine antifouling paint as claimed in claim 1, wherein in the moisture-curable acrylic resin, the groups for crosslinking are trialkoxysilyl groups; the group generates silicon hydroxyl through hydrolysis, and then Si-O-Si bonds are formed through condensation among the silicon hydroxyl, so that the room-temperature curing crosslinking of the coating is realized.
3. The zwitterionic-based environment-friendly marine antifouling paint as claimed in claim 2, wherein the trialkoxysilyl groups of the moisture-curable acrylic resin are trimethoxysilyl groups or triethoxysilyl groups.
4. The zwitterionic-based environmentally-friendly marine antifouling paint of claim 1, wherein the zwitterionic precursor siloxane is one of (N-triisopropylsilylacylpropyl) -3-aminopropyltrialkoxysilane, (N-methoxyacylethyl) -3-aminopropyltrialkoxysilane, and bis (N-methoxyacylethyl) -3-aminopropyltrialkoxysilane.
5. The zwitterionic-based environmentally-friendly marine antifouling paint of claim 1, wherein the organic antifouling antibacterial siloxane is at least one of 2- (2-hydroxy-3- (3- (trialkoxysilyl) propoxy) propyl) benzisothiazolin-3-one and 5-chloro-2- (2, 4-dichlorophenoxy) -N- (3- (trialkoxysilyl) propyl) aniline.
6. The zwitterionic-based environment-friendly marine antifouling paint as claimed in claim 1, wherein the inorganic nano bactericide is selected from nano ZnO and nano Cu 2 O, nano TiO 2 And/or nano Ag.
7. The zwitterionic-based environmentally-friendly marine antifouling paint of claim 1, wherein the auxiliaries comprise a paint leveling agent, a wetting agent and an antifoaming agent.
8. The zwitterionic-based environment-friendly marine antifouling paint as claimed in claim 1, wherein the solvent is one selected from butyl acetate, ethyl acetate, xylene, cyclohexanone and propylene glycol methyl ether acetate.
9. A method for preparing the zwitterion-based environment-friendly marine antifouling paint as claimed in any one of claims 1 to 8, characterized by comprising the following steps:
firstly, adding the inorganic nano bactericide into the moisture-curing acrylic resin, and carrying out high-speed shearing dispersion or sanding; after the inorganic nano bactericide is dispersed, sequentially adding the organic antifouling antibacterial siloxane, the zwitter ion precursor siloxane, the solvent, the aminosilane and the auxiliary agent, stirring and dispersing for 0.5-1.0 hour to obtain the required coating.
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