CN111808291A - Amphiphilic silicon-based functional polymer and preparation method and application thereof - Google Patents
Amphiphilic silicon-based functional polymer and preparation method and application thereof Download PDFInfo
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- CN111808291A CN111808291A CN202010594377.XA CN202010594377A CN111808291A CN 111808291 A CN111808291 A CN 111808291A CN 202010594377 A CN202010594377 A CN 202010594377A CN 111808291 A CN111808291 A CN 111808291A
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- China
- Prior art keywords
- functional polymer
- based functional
- polyethylene glycol
- silicon
- amphiphilic
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- 229920001002 functional polymer Polymers 0.000 title claims abstract description 51
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 title claims abstract description 47
- 229910052710 silicon Inorganic materials 0.000 title claims abstract description 47
- 239000010703 silicon Substances 0.000 title claims abstract description 47
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 15
- 239000001257 hydrogen Substances 0.000 claims abstract description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 10
- 230000002209 hydrophobic effect Effects 0.000 claims abstract description 10
- -1 polymethylsiloxane Polymers 0.000 claims description 51
- 239000003054 catalyst Substances 0.000 claims description 25
- 239000004698 Polyethylene Substances 0.000 claims description 21
- 229920000573 polyethylene Polymers 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 16
- 125000003342 alkenyl group Chemical group 0.000 claims description 15
- 229920000642 polymer Polymers 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 7
- 229920001223 polyethylene glycol Polymers 0.000 claims description 7
- 238000003756 stirring Methods 0.000 claims description 7
- 229920002545 silicone oil Polymers 0.000 claims description 6
- 239000011259 mixed solution Substances 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 239000002202 Polyethylene glycol Substances 0.000 claims description 4
- 150000001335 aliphatic alkanes Chemical group 0.000 claims description 4
- 239000000460 chlorine Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 229910000510 noble metal Inorganic materials 0.000 claims description 4
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- 239000004810 polytetrafluoroethylene Substances 0.000 claims description 4
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- 125000003277 amino group Chemical group 0.000 claims description 3
- 125000000524 functional group Chemical group 0.000 claims description 3
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- 125000000542 sulfonic acid group Chemical group 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 229910052763 palladium Inorganic materials 0.000 claims description 2
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- 229910052703 rhodium Inorganic materials 0.000 claims description 2
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- 230000003373 anti-fouling effect Effects 0.000 abstract description 20
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- 239000004205 dimethyl polysiloxane Substances 0.000 description 9
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 9
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 8
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- 229910052751 metal Inorganic materials 0.000 description 4
- 239000002184 metal Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
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- CRSBERNSMYQZNG-UHFFFAOYSA-N 1-dodecene Chemical compound CCCCCCCCCCC=C CRSBERNSMYQZNG-UHFFFAOYSA-N 0.000 description 2
- ZSZRUEAFVQITHH-UHFFFAOYSA-N 2-(2-methylprop-2-enoyloxy)ethyl 2-(trimethylazaniumyl)ethyl phosphate Chemical compound CC(=C)C(=O)OCCOP([O-])(=O)OCC[N+](C)(C)C ZSZRUEAFVQITHH-UHFFFAOYSA-N 0.000 description 2
- YTTILRPAYBZIKQ-UHFFFAOYSA-N 3-[2-(2-methoxyethoxy)ethoxy]prop-1-ene Chemical compound COCCOCCOCC=C YTTILRPAYBZIKQ-UHFFFAOYSA-N 0.000 description 2
- LBJZZFXUVYHXPH-UHFFFAOYSA-N 3-prop-2-enoxypropanoic acid Chemical compound OC(=O)CCOCC=C LBJZZFXUVYHXPH-UHFFFAOYSA-N 0.000 description 2
- HGFDRTHFFJPDNE-UHFFFAOYSA-N 7-chlorohept-1-ene Chemical compound ClCCCCCC=C HGFDRTHFFJPDNE-UHFFFAOYSA-N 0.000 description 2
- 108091003079 Bovine Serum Albumin Proteins 0.000 description 2
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 2
- 102000018697 Membrane Proteins Human genes 0.000 description 2
- 108010052285 Membrane Proteins Proteins 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- 230000000845 anti-microbial effect Effects 0.000 description 2
- 229940098773 bovine serum albumin Drugs 0.000 description 2
- BERDEBHAJNAUOM-UHFFFAOYSA-N copper(I) oxide Inorganic materials [Cu]O[Cu] BERDEBHAJNAUOM-UHFFFAOYSA-N 0.000 description 2
- KRFJLUBVMFXRPN-UHFFFAOYSA-N cuprous oxide Chemical compound [O-2].[Cu+].[Cu+] KRFJLUBVMFXRPN-UHFFFAOYSA-N 0.000 description 2
- 229940112669 cuprous oxide Drugs 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
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- 239000000314 lubricant Substances 0.000 description 2
- 238000005498 polishing Methods 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
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- 229920003026 Acene Polymers 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
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- 241000251468 Actinopterygii Species 0.000 description 1
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
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- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- BQCADISMDOOEFD-UHFFFAOYSA-N Silver Chemical compound [Ag] BQCADISMDOOEFD-UHFFFAOYSA-N 0.000 description 1
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- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
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- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
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- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/46—Block-or graft-polymers containing polysiloxane sequences containing polyether sequences
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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- 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
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
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- 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
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- 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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- 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
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- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/392—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing sulfur
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- C08J9/36—After-treatment
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- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
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- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
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- C08J2327/00—Characterised by the use of 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 a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of 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 a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/12—Characterised by the use of 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 a halogen; Derivatives of such polymers not modified by chemical after-treatment containing fluorine atoms
- C08J2327/18—Homopolymers or copolymers of tetrafluoroethylene
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- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
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Abstract
The invention discloses an amphiphilic silicon-based functional polymer and a preparation method and application thereof, belonging to the technical field of high molecular materials. The silicon-based functional polymer has an adjustable hydrophilic/hydrophobic microphase separation surface, a charge neutral surface and a hydrogen bond accepting surface, has good broad-spectrum marine fouling organism adsorption resistance, has a wide application prospect in the aspect of marine antifouling, and has the advantages of simple and feasible synthesis process, good pollution resistance broad-spectrum property, environmental friendliness, high yield, low preparation cost and easy popularization.
Description
Technical Field
The invention belongs to the technical field of high molecular materials, and particularly relates to an amphiphilic silicon-based functional polymer, and a preparation method and application thereof.
Background
With the increasing frequency of global trade activities, the transportation industry has been developed vigorously. In terms of energy efficiency, waterway transportation is far better than aviation, road and railway transportation, the global waterway transportation industry is continuously expanded to form ships with larger volume and stronger power. The waterway transportation of China is developed vigorously, and as early as 2005, the waterway transportation amount of China reaches 21.96 million t, and the container transportation amount is 2.1992 million t according to the statistical data of the Ministry of communication of the people's republic of China, wherein 1396.15 million TEUs (20-foot containers are 1 standard box TEU) are transported by ocean, and the acceleration rate is increased by 15.6% every year. Although the energy saving efficiency of waterway transportation is better, the energy consumption is also quite large due to the rapid development of the global waterway transportation industry, and the greenhouse effect and the air pollution are aggravated.
The problem of marine biofouling is one of the major causes of high energy consumption for the water shipping industry, and costs up to $ 2000 million each year. Can cause marine fouling of more than 2000 species, and animals (more than 1300 species) such as barnacle, Concha Ostreae, calx, sea squirt, Bryozoans, mussels, and sea anemone; the plants (more than 600 kinds) such as seaweed, diatom, water cloud and enteromorpha, wherein more than 50 kinds of marine fouling organisms are common.
After marine organisms are attached to the bottom of a ship sailing in seawater, the quality and sailing resistance of the ship can be increased, the sailing speed is reduced, the fuel consumption is correspondingly increased, and the abrasion degree of mechanical equipment parts is increased. The adhesion of marine fouling organisms can cause the metal surface protective film to be damaged, so that the metal is directly exposed in seawater, the electrochemical balance of the metal surface can be changed, the metal corrosion is accelerated, and the maintenance frequency of the ship is increased. It has been reported that a ship with marine pollutants attached thereto will consume 40% more oil than a clean hull, thereby increasing the greenhouse effect and harming the environment. Meanwhile, the ship bottom fouling greatly increases the roughness of the ship shell, so that the navigation resistance of the ship is increased, and the fuel consumption is increased.
In order to reduce the adhesion of marine fouling organisms on ships, various antifouling technologies are researched, but the coating of antifouling paint is the cheapest, most effective and most convenient way to solve the problem of marine organism adhesion. The antifouling paint products used by the prior ships mainly comprise cuprous oxide antifouling paint, organic antifouling paint, inorganic self-polishing antifouling paint and low-surface-energy antifouling paint. The cuprous oxide antifouling paint generally has unstable poison leaching rate, rough surface and poor broad spectrum, and particularly accelerates the release of an antifouling agent due to poor mechanical strength and high-speed stripping action of a coating when a ship sails, so that only the pollution to the marine ecological environment is increased; the tin-free self-polishing antifouling paint has reduced or even no effect on antifouling effect if the ship speed is too low or the berthing time is too long; the low surface energy antifouling paint is basically nontoxic and has the minimum influence on marine ecology, but the static antifouling effect is not ideal enough, and the low surface energy antifouling paint can only be used for dynamic antifouling and has the problems of poor adhesion with a bottom layer anticorrosive paint, no inhibition effect on adhesion of bryophytes and algae and the like. Therefore, an antifouling paint with excellent performance should have the advantages of good antifouling effect, long effective antifouling period, economy, small influence on the environment (no heavy metal, no insecticide) and the like.
Some hydrophobic silicon-based super-lubricating materials have been developed at present, and the purpose of reducing the adsorption of marine fouling organisms is achieved by utilizing a hydrophobic surface. While these coatings can be effective in reducing the low adhesion problems of barnacles, mussels etc., the hydrophobic nature of the surface attracts other organisms such as diatoms, leading to a constant growth in the hull mucus, still causing a large degree of hydrodynamic drag.
Disclosure of Invention
The invention aims to: aiming at the problems that the prior art lacks of excellent antifouling materials aiming at pollutants and marine biofouling, the prepared antifouling paint only aims at partial pollutants, and the related application is limited, an amphiphilic silicon-based functional polymer, and a preparation method and application thereof are provided.
The technical scheme adopted by the invention is as follows:
an amphiphilic silicon-based functional polymer, the structural formula is as follows:
wherein R is
R1Is H,
The preparation method of the amphiphilic silicon-based functional polymer comprises the following steps:
s1, uniformly mixing polymethylsiloxane containing active hydrogen with a functional compound containing alkenyl or a polymer with terminal alkenyl functional groups to obtain a mixed solution;
s2, adding a noble metal catalyst into the mixed liquor obtained in the step S1, and stirring and reacting for 10-20h at room temperature in an open system to obtain the catalyst.
Further, the structural formula is: the structural formula is as follows:
wherein R is
R1Is H,
Furthermore, the molar ratio of the polymethylsiloxane containing active hydrogen in S1 to the functionalized compound containing alkenyl or the polymer functionalized by terminal alkenyl is 1: 1-100.
Further, the functionalized compound containing alkenyl group or the polymer functionalized by terminal alkenyl group in S1 is a polymer chain containing alkenyl group, a charge neutral zwitterion, a hydrophilic polyethylene glycol chain, a hydrophobic alkane chain of which the other terminal group contains chlorine, bromine, hydroxyl, carboxyl, sulfonic acid group, amino group, quaternary ammonium salt, or a combination of repeating units of one or more of the foregoing compounds.
Further, the polymer functionalized by the end-group alkenyl in the S1 is at least one of polyethylene glycol-block-polyethylene, polyethylene glycol-block-polytetrafluoroethylene, polyethylene glycol-block-polystyrene, polyethylene glycol-block-polyolefin, polyethylene glycol-block-polyvinyl chloride, polyethylene glycol-block-polycaprolactone or polyethylene glycol-block-polymethacrylic acid-1H, 1H-perfluorooctyl ester.
Further, the noble metal catalyst in S2 is platinum, palladium, rhodium, silver, or ruthenium.
Further, the ratio of the catalyst to the polymethylsiloxane in S2 is 1.5 to 3 μ L: 1g of a compound; preferably 3 μ L: 1g of the total weight of the composition.
The functional group of the invention can be added with polymethyl siloxane containing active hydrogen under the action of a catalyst to form a compound containing alkenyl. Provided that the reaction is carried out for 10 to 20 hours, preferably 15 hours, at room temperature in an open system.
According to the invention, the charge neutral amphipathy is realized by the following two ways, firstly, the charge neutral amphipathy is realized by modifying polydimethylsiloxane and a charge neutral compound on a hydrophobic polymethyl siloxane side chain containing active hydrogen; and secondly, modifying polydimethylsiloxane, a compound with positive charges and negative charges and a polymethylsiloxane side chain containing active hydrogen simultaneously to realize charge neutral amphipathy.
The charge neutral compounds are mainly three types, namely phosphorylcholine zwitterions (such as 2-methacryloyloxyethyl phosphorylcholine), sulfobetaine zwitterions (such as sulfobetaine methacrylate and 3- (methacrylamide) propyl-dimethyl (3-sulfonic acid) ammonium hydroxide) and carboxylic betaine zwitterions (such as 2- (2-methacryloyloxyethyl dimethylamino) acetate). The compound with positive charges is a quaternary ammonium salt compound, and the compound with negative charges is a compound containing carboxyl, sulfonic acid group and phosphoric acid group.
The second way is to modify an amphiphilic chain segment on a hydrophobic polymethylsiloxane side chain, and realize the hydrophilic-hydrophobic difference on the same chain segment, wherein the amphiphilic chain segment can be: polyethylene glycol-block-polyethylene, polyethylene glycol-block-polytetrafluoroethylene, polyethylene glycol-block-polystyrene, polyethylene glycol-block-polyacene, polyethylene glycol-block-polyvinyl chloride, polyethylene glycol-block-polycaprolactone, polyethylene glycol-block-polymethacrylic acid-1H, 1H-perfluorooctyl ester, and the like.
Therefore, the invention realizes the amphiphilic surface by modifying the hydrophilic chain segment and the hydrophobic chain segment on the hydrophobic polymethylsiloxane side chain and utilizing the microphase separation caused by different hydrophilicity and hydrophobicity of the polymer material, thereby effectively reducing the adsorption of organisms such as diatom which are only resistant to the hydrophobic surface and the adsorption of barnacles, mussels and the like which are resistant to the hydrophilic surface. The charged neutral molecules and the chlorine-containing molecules have good antibacterial performance, and can realize the antibacterial attachment and fouling of the material.
In addition, because alkynyl, hydroxyl, carboxyl and the like are introduced into the end group on the polymethyl siloxane main chain, the polymer chain is fixed on the chemical surface under the action of a chemical bond, ideal chemical fixation is realized, and compared with the fixation of common physical coating, the adhesion capability of the coating can be greatly improved, and the mechanical property of the coating is further improved. Effectively solves the problems in practical application, such as paint bubbling above fish eyes and waterlines, coating falling, poor mechanical property and the like.
Furthermore, the prepared amphiphilic polymer can be directly bound to the surface of the substrate, and the liquid polymer brush with the super-smooth function is prepared.
The amphiphilic silicon-based functional polymer is applied to preparation of marine organism fouling resistant products.
Further, the amphiphilic silicon-based functional polymer is mixed with silicone oil and coated on the surface needing to resist marine organism fouling.
Further, using a mixture of the amphiphilic silicon-based functional polymer and silicone oil, a lubricant containing a hydrophilic component can be prepared, which can be impregnated into a porous substrate to obtain a super-smooth surface.
Further, the mixture of the amphiphilic silicon-based functional polymer and the silicone oil is directly bound to the surface of the substrate, so that the liquid polymer brush with the super-smooth function can be prepared.
In summary, due to the adoption of the technical scheme, the invention has the beneficial effects that:
1. the amphiphilic silicon-based functional polymer has an adjustable amphiphilic surface, and the amphiphilic surface caused by microphase separation can effectively reduce the adsorption of marine fouling organisms; the charged neutral surface and the surface receiving hydrogen bonds can effectively avoid protein adsorption, and the charged neutral surface and the surface receiving hydrogen bonds can introduce chlorine-containing molecules and simultaneously show excellent antibacterial attachment and fouling resistance;
2. the amphiphilic silicon-based functional polymer has an adjustable surface structure, can effectively reduce the adsorption of marine fouling organisms, and has a wide application prospect in the aspect of marine organism fouling resistance;
3. the preparation method of the amphiphilic silicon-based functional polymer has the advantages of simple and feasible process, environmental protection, high yield, low preparation cost and easy popularization.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present invention, the drawings needed to be used in the embodiments will be briefly described below, it should be understood that the following drawings only illustrate some embodiments of the present invention and therefore should not be considered as limiting the scope, and for those skilled in the art, other related drawings can be obtained according to the drawings without inventive efforts.
FIG. 1 is a nuclear magnetic diagram of an amphiphilic silicon-based functional polymer prepared in example 1;
FIG. 2 is an optical microscope image of the amphiphilic silicon-based functional polymer in a porous state;
FIG. 3 is a diagram of an embodiment of the amphiphilic silicon-based functional polymer of the present invention;
FIG. 4 is a porous super-slip diagram of an amphiphilic silicon-based functional polymer of the present invention;
FIG. 5 is a drawing showing the protein adsorption resistance of the amphiphilic silicon-based functional polymer surface coating material according to the present invention;
FIG. 6 is an antibacterial pattern of the amphiphilic silicon-based functional polymer surface coating material of the present invention.
Detailed Description
In order to make the objects, technical solutions and advantages of the present invention more apparent, the present invention is described in further detail below with reference to the accompanying drawings and embodiments. It should be understood that the detailed description and specific examples, while indicating the preferred embodiment of the invention, are intended for purposes of illustration only and are not intended to limit the scope of the invention. The components of embodiments of the present invention generally described and illustrated in the figures herein may be arranged and designed in a wide variety of different configurations.
Thus, the following detailed description of the embodiments of the present invention, presented in the figures, is not intended to limit the scope of the invention, as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be derived by a person skilled in the art from the embodiments of the present invention without making any creative effort, shall fall within the protection scope of the present invention.
It is noted that relational terms such as "first" and "second," and the like, may be used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Also, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising an … …" does not exclude the presence of other identical elements in a process, method, article, or apparatus that comprises the element.
The features and properties of the present invention are described in further detail below with reference to examples.
Example 1
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 5g of monovinyl-terminated polydimethylsiloxane (molecular weight 2000) and 5g of monovinyl-terminated poly (ethylene glycol) (molecular weight 500) are stirred and mixed uniformly, then 15 mu L of platinum catalyst is added, and stirring is carried out overnight at room temperature, thus obtaining the catalyst. This example produces a viscous liquid polyethylene glycol functionalized amphiphilic silicon-based functional polymer. The nuclear magnetic diagram is shown in FIG. 1.
Example 2
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 5g of 1-dodecene and 5g of monovinyl-terminated poly (ethylene glycol) (molecular weight 500) are stirred and mixed uniformly, then 15 mu L of Pt catalyst is added, and the mixture is stirred at room temperature overnight to obtain the catalyst. This example produces a viscous liquid amphiphilic silicon-based functional polymer functionalized with alkyl groups and polyethylene glycol chains.
Example 3
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 2g of single vinyl end group polydimethylsiloxane (molecular weight 2000), 5g of 3- [ N, N-dimethyl- [2- (2-methylpropane-2-enoyloxy) ethyl ] ammonium ] propane-1-sulfonic acid inner salt are stirred and mixed uniformly, then 30 mu L of catalyst is added, and the mixture is stirred at room temperature overnight, thus obtaining the catalyst. This example produces an amphiphilic silicon-based functional polymer functionalized with amphiphilic zwitterions in a viscous liquid.
Example 4
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 2g of monovinyl end-group polydimethylsiloxane (molecular weight 2000) and 4g of 2-methacryloyloxyethyl phosphorylcholine are stirred and mixed uniformly, then 30 mu L of catalyst is added, and the mixture is stirred at room temperature overnight to obtain the catalyst. This example produces an amphiphilic silicon-based functional polymer functionalized with amphiphilic zwitterions in a viscous liquid.
Example 5
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
the preparation method comprises the following steps of uniformly stirring and mixing 10g of polymethylsiloxane, 1g of 7-chloro-1-heptene, 5g of diethylene glycol allyl methyl ether and 2g of monovinyl end-group polydimethylsiloxane (molecular weight 2000), adding 30 mu L of Pt catalyst, and stirring at room temperature overnight to obtain the catalyst. This example produces a viscous liquid amphiphilic chlorine-substituted silicon-based functional polymer.
Example 6
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 2g of 7-bromo-1-heptene, 5g of diethylene glycol allyl methyl ether and 2g of monovinyl end-group polydimethylsiloxane (molecular weight 2000) are stirred and mixed uniformly, then 30 mu L of Pt catalyst is added, and the mixture is stirred at room temperature overnight to obtain the catalyst. This example produced a viscous amphiphilic bromine-substituted silicon-based functional polymer.
Example 7
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 3g of 3-allyloxypropionic acid, 2g of monovinyl-terminated polydimethylsiloxane (molecular weight 2000) and 2g of poly (ethylene glycol) acrylate (molecular weight 500) are stirred and mixed uniformly, then 30 mu L of Pt catalyst is added, and the mixture is stirred at room temperature overnight to obtain the catalyst. This example produces a carboxy-functionalized amphiphilic silicon-based functional polymer in a viscous liquid.
Example 8
The preferred embodiment of the invention provides a preparation method of an amphiphilic silicon-based functional polymer, which comprises the following specific steps:
10g of polymethylsiloxane, 13g of 3-allyloxypropionic acid and 14g of 7-chloro-1-heptene are stirred and mixed uniformly, then 30 mu L of catalyst is added, and the mixture is stirred at room temperature overnight to obtain the catalyst. This example produces a pale yellow viscous liquid amphiphilic chlorine-substituted silicon-based functional polymer.
Example 9
Taking 10g of the amphiphilic bromine-substituted silicon-based functional polymer prepared in the embodiment 6, adding 5mL of tetrahydrofuran, adding 6g of ethylenediamine, refluxing at 70 ℃ overnight, and heating to evaporate the solvent to obtain the amino-alkane functionalized silicon-based functional polymer. This example produces a slightly yellow viscous liquid amphiphilic silicon-based functional polymer functionalized with hydrophilic amino groups and hydrophobic linear alkanes.
Example 10
Taking 10g of the amino and alkane functionalized silicon-based functional polymer prepared in the embodiment 8, adding 5mL of tetrahydrofuran, adding 6g of ethylenediamine, refluxing at 70 ℃ overnight, and then heating to evaporate the solvent to obtain the amino and carboxyl functionalized silicon-based functional polymer. This example produces a slightly yellow viscous liquid hydrophilic carboxyl-and amino-functionalized amphiphilic silicon-based functional polymer.
Example 11
Dissolving 1g of the product prepared in example 1 in 100g of silicone oil, and uniformly stirring to obtain a mixed solution; the mixed liquid was then poured into a polytetrafluoroethylene porous membrane (0.45 μm). The solution-containing super-smooth porous surface was prepared by allowing the excess lubricant to drain off vertically overnight, and the porous state thereof is shown in FIG. 2. The physical diagram of the liquid drop-free liquid drop and the liquid drop-containing liquid drop is shown in figure 3.
Example 12
Dissolving 1g of the product prepared in example 1 in 100g of silicone oil, and uniformly stirring to obtain a mixed solution; then, mixing the mixed solution and 100g of Dow Corning polydimethylsiloxane prepolymer according to the volume ratio of 10: 1 and mixing. The resulting viscous liquid was placed in a vacuum oven to remove air, then coated on a substrate and cured in an oven at 70 ℃ for 24 hours to produce a super-slippery gel coating, as shown in fig. 4 (surface droplets are beads), indicating that a super-slippery surface was successfully produced.
Example 13
1g of the liquid prepared in example 5 was dissolved in 20mL of a dry tetrahydrofuran solution. And (3) washing the clean glass substrate by using acetone, treating the surface for 20min by using plasma, immediately coating the solution on the glass surface after taking out, drying at room temperature overnight, then placing in an oven, and treating at 70 ℃ for 6h to obtain the protein-resistant surface.
Taking a normal surface and an anti-protein surface with the specification of 10 multiplied by 10cm, placing the two surfaces in 10mL solution containing bovine serum albumin (10mg/mL), prohibiting 24 hours, then taking 1mL solution, adding 5mL of 0.1mg/mL Coomassie brilliant blue solution, dyeing for 5 minutes, measuring the light absorption intensity at 595nm, and calculating the adsorption rate of the two surfaces to the bovine serum albumin according to the light absorption intensity. The effect of anti-protein adsorption is shown in FIG. 5. As can be seen from the figure, compared with the normal surface, the amphiphilic surface protein adsorption rate of the surface coating material of the product coated by the invention is greatly reduced.
Example 14
1g of the liquid prepared in example 5 was dissolved in 20mL of a dry tetrahydrofuran solution. Washing the clean glass substrate with acetone, treating the surface with plasma for 20min, taking out, immediately coating the solution on the glass surface, drying at room temperature overnight, then placing in an oven, and treating at 50 ℃ for 6 h. An antimicrobial surface is obtained.
Respectively inoculating gram-positive staphylococcus to the normal surface and the antibacterial surface, culturing at 37 ℃ for 24h, and analyzing under a fluorescence microscope after dyeing to obtain the antibacterial effects of the two surfaces. The antimicrobial effect is shown in fig. 6. As can be seen from the figure, compared with the normal surface, the amphiphilic antibacterial surface protein bacteriostasis rate of the surface coating material coated by the product is greatly improved.
The above description is only for the purpose of illustrating the preferred embodiments of the present invention and is not to be construed as limiting the invention, and any modifications, equivalents and improvements made within the spirit and principle of the present invention are intended to be included within the scope of the present invention.
Claims (10)
1. An amphiphilic silicon-based functional polymer is characterized in that the structural formula is as follows:
wherein R is
-OH or-COOH;
R1is H,
2. The method of claim 1, wherein the structural formula of the amphiphilic silicon-based functional polymer is:
wherein R is
-OH or-COOH;
R1is H
3. The method for preparing amphiphilic silicon-based functional polymer according to claim 1 or 2, comprising the steps of:
s1, uniformly mixing polymethylsiloxane containing active hydrogen with a functional compound containing alkenyl or a polymer with terminal alkenyl functional groups to obtain a mixed solution;
s2, adding a noble metal catalyst into the mixed liquor obtained in the step S1, and stirring and reacting for 10-20h at room temperature in an open system to obtain the catalyst.
4. The method for preparing amphiphilic silicon-based functional polymer according to claim 3, wherein the molar ratio of the polymethylsiloxane containing active hydrogen in S1 to the alkenyl-containing functional compound or the terminal alkenyl-functional polymer is 1: 1-100.
5. The method according to claim 3, wherein the functionalized alkenyl-containing compound in S1 is a neutral-charged zwitterion containing alkenyl, a hydrophilic polyethylene glycol chain, a hydrophobic alkane chain with a terminal group at the other end containing chlorine, bromine, hydroxyl, carboxyl, sulfonic acid group, amino group, quaternary ammonium salt, or a polymer chain with repeating units of one or more of the foregoing compounds.
6. The method of claim 3, wherein the functionalized polymer with terminal alkenyl group in S1 is at least one of polyethylene glycol-block-polyethylene, polyethylene glycol-block-polytetrafluoroethylene, polyethylene glycol-block-polystyrene, polyethylene glycol-block-polyolefin, polyethylene glycol-block-polyvinyl chloride, polyethylene glycol-block-polycaprolactone, or polyethylene glycol-block-polymethacrylic acid-1H, 1H-perfluorooctyl ester.
7. The method of claim 3, wherein the noble metal catalyst in S2 is Pt, Pd, Rh, Ag or Ru.
8. The method for preparing amphiphilic silicon-based functional polymer according to claim 3, wherein the ratio of the catalyst to the polymethylsiloxane in S2 is 1.5-3 μ L: 1g of the total weight of the composition.
9. Use of the amphiphilic silicon-based functional polymer according to claim 1 or 2 for the preparation of a product resistant to marine biofouling.
10. The use according to claim 9, wherein the amphiphilic silicon-based functional polymer is mixed with silicone oil and applied to a surface to be protected against marine biofouling.
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