CN106634562B - A kind of Capsaicinoid parents network marine anti-pollution coating and its methods for making and using same - Google Patents
A kind of Capsaicinoid parents network marine anti-pollution coating and its methods for making and using same Download PDFInfo
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- CN106634562B CN106634562B CN201610903175.2A CN201610903175A CN106634562B CN 106634562 B CN106634562 B CN 106634562B CN 201610903175 A CN201610903175 A CN 201610903175A CN 106634562 B CN106634562 B CN 106634562B
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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
- C09D181/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing sulfur, with or without nitrogen, oxygen, or carbon only; Coating compositions based on polysulfones; Coating compositions based on derivatives of such polymers
- C09D181/02—Polythioethers; Polythioether-ethers
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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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/04—Polythioethers from mercapto compounds or metallic derivatives thereof
- C08G75/045—Polythioethers from mercapto compounds or metallic derivatives thereof from mercapto compounds and unsaturated compounds
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- 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
- C09D5/14—Paints containing biocides, e.g. fungicides, insecticides or pesticides
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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
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Abstract
The present invention provides a kind of Capsaicinoid parents network marine anti-pollution coating and its methods for making and using sames.The preparation method of Capsaicinoid parents' network marine anti-pollution coating characterized by comprising carry out Friedel-Crafts reaction using guaiacol and unsaturated amides and obtain Capsaicinoid structures alone；Resulting Capsaicinoid structures alone and unsaturated multi-functional crosslinking agent and mercaptothiols are obtained into Capsaicinoid parents' network marine anti-pollution coating through photo-initiated crosslinking.Marine anti-pollution coating obtained by the present invention has the advantage that its mechanical strength, modulus and substrate adherence are higher than general nonpolluting coating, it is almost non-swelling in the seawater, there are extremely strong inhibition and desorption to the adherency of fouling organism common in ocean.Also there is sterilizing function, protein adsorption and bacterial adhesion can be resisted simultaneously, double shielding can be played the role of to coating.
Description
Technical field
The invention belongs to marine anti-pollution polymeric material fields, and in particular to a kind of parents' net for Capsaicinoid structure
The preparation method of network nonpolluting coating can be used for the formation on surfaces such as marine ships and have both antifouling and antibacterial action low-surface-energy ring
The cross-linked network nonpolluting coating of border friendly.
Background technique
In the development process to ocean, due to the appearance of biodeterioration situation, people gradually appreciate nonpolluting coating
Importance.Nonpolluting coating not only can protect submerged structure from corroding, while save the energy for navigation ship.Therefore it opens
Sending out nonpolluting coating effective has far-reaching significance.
Marine anti-pollution coating commercially available at present is still to discharge poisonous anti-fouling agent as main antifouling means, meeting
Significant damage is generated to marine environment, therefore developing nontoxic environmentally friendly nonpolluting coating has been trend of the times.In view of capsaicine
Good antifouling sterilization ability, the preparation research in recent years in relation to capsaicine anti-fouling material are very active.Wherein, it mostly uses greatly peppery
Green pepper element is added directly in coating or is reacted with coating material as marine anti-pollution additive, and it is aobvious to prepare anti-fouling effect
It writes, lower-cost environmentally friendly coating.The disadvantage is that mixed capsaicine be easy oozed out from coating, the antifouling period it is shorter from
And influence anti-fouling effect.
Low-surface-energy nonpolluting coating is a kind of nonpolluting coating of nontoxic easy-stripping type, is mainly had using material itself
Low-surface-energy reduces various organisms in the adhesion strength on its surface, so that fouling organism is difficult to adhere to or adhere to loosely, in sea
To achieve the effect that antibiont adherency and pollution under the souring of water.Therefore, low surface energy coat is a kind of with good
The anti-fouling material of application prospect.
Summary of the invention
The object of the present invention is to provide a kind of Capsaicinoid parents network low surface energy for marine nonpolluting coating and its preparation and
Using the coating has low-surface-energy and elasticity modulus, good chemical stability and weatherability, excellent with substrate adhesive property
It is different, while avoiding having used toxic antifouling reagent, it is expected to become a kind of advanced environmentally friendly nonpolluting coating material, it can be with
Overcome in marine anti-pollution coating traditional at present, it largely can be raw to ocean using poisonous anti-fouling agent (organotin, cuprous oxide etc.)
State environment and human health cause to seriously endanger, though and the silicon substrate of low-surface-energy or fluoro resin silicone oil have good desorption
Performance, but, anti-pollution insufficient defect poor with substrate adherence.
In order to achieve the above object, the present invention provides a kind of preparation sides of Capsaicinoid parents network marine anti-pollution coating
Method characterized by comprising carry out Friedel-Crafts reaction using guaiacol and unsaturated amides and obtain Capsaicinoid structure
Monomer (HMBA)；Resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking obtains Capsaicinoid parents' network marine anti-pollution coating.
Preferably, the unsaturated amides are N hydroxymethyl acrylamide or hydroxyethyl acrylamide class monomer.
Preferably, the mercaptothiols are poly dimethyl sulfydryl siloxanes, trimethylolpropane tris (3- mercaptopropionic acid
Ester), at least one of trimethylolpropane tris (2- mercaptoacetate) and four (3- mercaptopropionic acid) pentaerythritol esters.
Preferably, the multi-functional crosslinking agent of unsaturation is polyethyleneglycol diacrylate and cyanuric acid triolefin
At least one of propyl ester.
Preferably, described to utilize guaiacol and unsaturated amides to carry out Friedel-Crafts reaction to obtain Capsaicinoid knot
The specific steps of structure monomer include: unsaturated amides to be dissolved in solvent A, then guaiacol and deicer are added thereto,
It is placed in after stirring 30-60min in ice-water bath, catalyst is added dropwise dropwise and ice-water bath is removed, in 35-60 after reaction 2-10 hours
Continuous heating stirs progress Friedel-Crafts reaction in 3-7 days in DEG C oil bath pan, after reaction, white with filtered on buchner funnel acquisition
Color precipitating is Capsaicinoid (HMBA) crude product；Wherein, unsaturated amides, guaiacol, deicer, catalyst, solvent A
Weight ratio is 10: 12.5-62.5: 2.4-12: 5-25: 50-250.
It is highly preferred that described carries out Friedel-Crafts reaction acquisition Capsaicinoid using guaiacol and unsaturated amides
The specific steps of structures alone further include: the Capsaicinoid (HMBA) of purification is obtained by recrystallization.
It is highly preferred that the deicer is anhydrous magnesium sulfate or calcium hydride.
It is highly preferred that the catalyst is the concentrated sulfuric acid or hydrochloric acid.
It is highly preferred that the specific steps of the recrystallization include: that solvent is added into Capsaicinoid (HMBA) crude product
A is heated to being completely dissolved, and the impurity in the solution of filtering removal while hot, filtrate stands cooling, to which there is no crystallizations to be precipitated in filtrate
Afterwards, then it is filtered the HMBA for obtaining purification, is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
Preferably, described by resulting Capsaicinoid structures alone and unsaturated multi-functional crosslinking agent and sulfydryl
The specific steps that mercaptan obtains Capsaicinoid parents' network marine anti-pollution coating through photo-initiated crosslinking include: by Capsaicinoid
(HMBA) it is dissolved in solvent B with mercaptothiols and unsaturated multi-functional crosslinking agent, adds room temperature after photoinitiator
Lower stirring forms uniform solution, is then filtered to solution, obtains crosslinked fluid, pipettes a certain amount of crosslinked fluid coated on substrate table
On face, 5-20min is irradiated under ultraviolet light and carries out photocuring, the substrate after solidification is placed under infrared lamp, so that partial solvent B
Volatilization, is finally impregnated and is dried with solvent B to remove the raw material and solvent B that coating surface does not react completely, obtain Capsaicinoid
Parents' network marine anti-pollution coating.
It is highly preferred that the photoinitiator is 4-dimethylaminopyridine (DMAP) or 2- hydroxy-2-methyl phenyl third
Alkane -1- ketone (HMPP).
It is highly preferred that the additional amount of the photoinitiator is the 0.05%-1% of reaction system total weight.
It is highly preferred that double bond contained by the Capsaicinoid, unsaturated multi-functional crosslinking agent and mercaptothiols with
The molar ratio of sulfydryl is 1: 1,2: 1 or 0.5: 1.
It is highly preferred that the intensity of the ultraviolet light is 1-10mW/cm2。
It is highly preferred that the solvent A, solvent B are respectively ethyl alcohol, n,N-Dimethylformamide, N, N- dimethylacetamide
The mixture of one or more of amine and toluene.
The present invention also provides classes prepared by the preparation method of above-mentioned Capsaicinoid parents' network marine anti-pollution coating
Capsaicine parents' network marine anti-pollution coating.
Preferably, the contact angle of Capsaicinoid parents' network marine anti-pollution coating is 130-140 °, breaking strength
Reach 4-10MPa, swellbility in water is 0.5%-5.1%, and pencil hardness 3B-5H, adhesive force is 0-1 grades.
The acid resistance and alkalescent of Capsaicinoid parents' network marine anti-pollution coating of the invention are preferable, bovine serum albumin
(BSA) adsorbance can reduce 80-98%, can reduce 85-93% to the adherency of Phaeodactylum tricornutum, can to the adherency of stone mushroom
Reduce 72-83%.
Application the present invention also provides above-mentioned Capsaicinoid parents network marine anti-pollution coating in marine anti-pollution field.
It is highly preferred that Capsaicinoid parents' network marine anti-pollution coating is long-term as coating for watercraft, underwater equipment
Nonpolluting coating.
Compared with prior art, the beneficial effects of the present invention are:
The process conditions that the present invention uses are simple, and step is easy, and photocuring " sulfydryl-alkene " click chemistry cross-linking effect is good.
It introduces class Capsaicin structure and not uses common blending method, but enter material by the way of photocured cross-linked, it can be effective
It prevents Capsaicin from oozing out, and extends the antifouling period.In addition, artificial synthesized unsaturated class Capsaicin monomer structure with catechol due to having
There is similar bisphenol hydroxy structure that can effectively improve the adhesiveness of coating and substrate.Since main body uses mercaptan, improve
The elasticity modulus of material, enhances mechanical performance, imparts the extremely low surface energy of amphiphilic network, thus has under seawater scouring
Good desorption effect.Obtained marine anti-pollution coating has the advantage that its mechanical strength, modulus and substrate adherence are high
It is almost non-swelling in the seawater in general nonpolluting coating, there is extremely strong suppression to the adherency of fouling organism common in ocean
System and desorption.Also there is sterilizing function, protein adsorption and bacterial adhesion can be resisted simultaneously, bilayer can be played to coating
Protective effect.In addition, preparation method is easy, noxious material is not discharged, has environmentally friendly feature, is suitable for a variety of substrates
There is very strong industrial prospect on surface.
Detailed description of the invention
Fig. 1 is the infrared spectrum of Capsaicinoid structure.
Fig. 2 is Capsaicinoid structure1H-NMR spectrum.(solvent: DMSO-d6)
Fig. 3 is the photo of parents' network coating in glass plate and embodiment 2-4.(3: 7,5: 5,7: 3 be HMBA and crosslinking agent
Proportion)
Fig. 4 is blank glass plate and 8 floating coat of embodiment about BSA, and the desorption of diatom, stone mushroom tests histogram.
Fig. 5 is parents' network coating in embodiment 2-4 to the sterilizing rate situation of Escherichia coli.(3: 7,5: 5,7: 3 be HMBA
It is matched with crosslinking agent)
Specific embodiment
Present invention will be further explained below with reference to specific examples.It should be understood that these embodiments are merely to illustrate the present invention
Rather than it limits the scope of the invention.In addition, it should also be understood that, after reading the content taught by the present invention, those skilled in the art
Member can make various changes or modifications the present invention, and such equivalent forms equally fall within the application the appended claims and limited
Range.
Additive amount, content and the concentration of many kinds of substance is referred to herein, wherein described " part ", unless otherwise indicated,
All refer to " parts by weight "；The percentage composition all refers to mass percentage unless otherwise indicated.
In the present invention, term " hydrophilic " and " hydrophily " indicate identical meaning.Term " hydrophobic " and " hydrophobicity " table
Show identical meaning.Term " amphiphilic " and the identical meaning of " amphipathic " expression, refer to while having hydrophily and hydrophobicity.
In the present invention, term " amphiphilic (property) copolymer networks ", " amphiphilic (property) network ", " parents (property) copolymer net
Network ", " parents (property) three metanetworks " indicate identical meaning.
Test assessment to the following technical indicator of progress that following each embodiments obtain:
One, test method and standard:
Contact angle test: 3ml deionized water is added dropwise in Capsaicinoid parents' network marine anti-pollution coating slide of preparation, sets
It is tested on the optical contact angle measuring instrument of model Dataphysis OCA40, each sample takes different 3 to click through
Row test, takes the arithmetic mean of instantaneous value of 3 test results.
Mechanical property (tensile strength, elongation at break) test: in universal testing machine (KEXIN, WDW3020, a Changchun
Section is new) in test at room temperature.Each sample is at least surveyed 5 times, to ensure the accuracy of measured value.
Swelling ratio is tested in water: by dry samples weighing, obtaining quality Wdry, it is then placed into deionized water.Impregnate 10
After it, sample is taken out from beaker, wipes clean sample surfaces residual liquid with test paper, is weighed, is obtained quality Wwet, then until
The quality of sample for 24 hours no longer changes.Swelling ratio (swellbility) Wt% is calculated as followsswelling:
Wt%swelling=100 × (Wwet-Wdry)/Wdry
Hardness test: according to GB/T6739-2006, the pencil of a set of known hardness is chosen, is respectively as hardness is incremented by
5B, 4B, 3B, 2B, HB, 1H, 2H, 3H, 4H, 5H and 6H, pencil point be in flat and smooth circular cross-section, and edge do not have clast and
Notch.Pencil and coating are in 45° angle light paddling coating surface, until most hard pencil model when being unable to scratch-resistant coatings indicates coating
Hardness.
Adhesive force test: it is operated according to GBT9286-1998 cross-hatching.First in coating surface vertical direction in length and breadth
Each stroke of 6 lines, it is necessary to scratch coating.Then it is gently touched with finger in coating surface, records coating shedding number.
International standard ISO is divided into six grades
0 grade: completely nothing falls off coating；
1 grade: coating shedding is not more than 5%；
2 grades: coating shedding is greater than 5%, is not more than 15%；
3 grades: coating shedding is greater than 15%, is not more than 35%；
4 grades: coating shedding is greater than 35%, is not more than 65%；
5 grades: coating shedding is greater than 65%；
Chemical resistance test
(1) alkali resistance: at room temperature, coating is immersed in the 20wt% alkalinity being formulated by sodium hydroxide and deionized water
In solution.After 24 hours, coating is taken out, gently wipes surface solution with filter paper.Observe coating surface phenomenon.
(2) acid resistance: at room temperature, it is molten that coating is immersed in the 20wt% acidity being formulated by dilute hydrochloric acid and deionized water
In liquid.After 24 hours, coating is taken out, method is same as above.
Note: E is intact, F bubble, C corrugation, R rupture, P removing
BSA adsorption test: configuring the BSA solution of 1mg/ml, coating be put into solution, and ultrasonic disperse 10 minutes, with shifting
Liquid pipe take BSA solution be added sample bottle in, be put into water bath chader, after being fullyd shake for 24 hours at 25 DEG C, take supernatant liquor from
The heart 20 minutes.Using UV detector, wavelength selective 2 80nm measures the concentration of BSA solution, calculates according to the following formula
Adsorbance q (ug/cm2):
Q=((C0-C1)×V)/S
C0The concentration of-BSA stoste, mg/ml；
The concentration of BSA solution, mg/ml after C1- absorption；
The area of S-APCN, cm2；
The volume of V-BSA solution, ml.
Indoor panel experiment: after the coating prepared drying, the diatom liquid or stone of seawater and f/2 nutritive salt are immersed in
In mushroom liquid, certain condition carries out culture 7 days in incubator.It is counted after the test using blood counting chamber, comparative coatings
Anti-pollution.
Anti-microbial property test: (concentration is 1 × 10 for the Escherichia coli bacteria liquid after taking normal saline dilution6cfu/mL)50μ
L is coated uniformly on the nonpolluting coating surface that diameter is 5cm under sterile working, cultivates 30min in 37 DEG C of constant incubators
After take out, the coating sample surface contacted with bacterium solution with 500 μ L normal saline flushings 10 times collects flushing liquor and 100 μ L is simultaneously taken to rush
Washing lotion is coated on solid medium, and constant temperature incubation is for 24 hours at 37 DEG C.Same process is also applied for the coating sample of comparative example
Product.The bacterium colony that next day observes and records surviving bacteria on solid medium forms number (i.e. bacterium colony concentration, cfu/mL).Sterilizing rate calculates
Formula are as follows:
Sterilizing rate (%)=(former clump count-surviving colonies number)/original clump count × 100%.
Two, experimental material:
Reagent is all that analysis is pure, is purchased from China Medicine (Group) Shanghai Chemical Reagent Co.,.Wherein, poly dimethyl sulfydryl silicon
Oxygen alkane (Mw=5500, sulfhydryl content 100%, Mw/Mn=2.1) ((sulfydryl) methylsiloxane-dimethylsiloxane copolymer
(manufacturer is U.S. GELEST company, model SMS-992), polyethyleneglycol diacrylate (Mw=400-600,
1.12g/mL) (ALFA), the mass fraction 98% of the concentrated sulfuric acid.
Embodiment 1
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides and obtain Capsaicinoid structures alone: by 10
Part N hydroxymethyl acrylamide is dissolved in 50 parts of ethyl alcohol, then 12.5 parts of guaiacol and 2.4 parts of anhydrous slufuric acids are added thereto
Magnesium is placed in after stirring 30min in ice-water bath, and 5 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice-water bath in 35 DEG C of oil after reaction 2 hours
Continuous heating stirs progress Friedel-Crafts reaction in 3 days in bath.After reaction, white precipitate is obtained with filtered on buchner funnel
As Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the specific steps of the recrystallization are obtained by recrystallization
Are as follows: 20 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, the impurity in the solution of filtering removal while hot.Filter
Liquid standing slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification, infrared spectrum
With1H-NMR spectrum is as depicted in figs. 1 and 2, is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By the Capsaicinoid HMBA of resulting purification (part, that is, molal quantity here, wherein HMBA and two propylene of polyethylene glycol
Acid esters is monomer containing double bonds, and poly dimethyl sulfydryl siloxanes is the hydrophobic monomer containing sulfydryl) 0.1 mole, poly dimethyl
1 mole of sulfydryl siloxanes and 0.9 mole of polyethyleneglycol diacrylate are dissolved in 5mL DMF, and photoinitiator 4- diformazan is added
Base aminopyridine DMAP, the additional amount of photoinitiator are the 0.5% of reaction system total weight, and stirring is formed uniform molten at room temperature
Liquid.Then solution is filtered with 0.22 μm of filter, obtains pure crosslinked fluid.1ml crosslinked fluid is pipetted every time to be coated on
On substrate (glass plate) surface, in ultraviolet light intensity 10mW/cm2Irradiation under carry out photocured cross-linked reaction 5min, after solidification
Substrate is placed under infrared lamp, so that partial solvent DMF volatilizees.It is finally impregnated and is dried with solvent DMF to remove coating surface
The raw material and solvent not reacted completely finally obtain Capsaicinoid parents' network marine anti-pollution coating.
The contact angle of marine anti-pollution coating produced by the present invention is 130 °, breaking strength 4MPa, and the swelling ratio in water is
0.5%, pencil hardness 3B, adhesive force are 0 grade, and acidproof and weak base, BSA adsorbance is 30ug/cm2, can relative to PDMSe
80% is reduced, the adhesive capacity of diatom is 150x103n/cm2, relative to PDMSe, 85% is reduced, the amount of stone mushroom spore adherency is
200x103n/cm2, relative to PDMSe, 72% is reduced, sterilizing rate reaches 75%, has splendid anti-fouling effect.
Embodiment 2
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 100 parts of ethyl alcohol, then 20 parts of guaiacol and 2.4 are added thereto
Part anhydrous magnesium sulfate, is placed in after stirring 30min in ice-water bath, and 8 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice water after reaction 2 hours
Bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 6 days.After reaction, it is obtained with filtered on buchner funnel
Obtaining white precipitate is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the recrystallization are obtained by recrystallization
Specific steps are as follows: into Capsaicinoid crude product be added 30 parts of ethyl alcohol, be heated to being completely dissolved, while hot filtering removal solution in
Impurity.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification, puts
After being placed in vacuum drying oven 35 DEG C of drying, it is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.3 mole of the Capsaicinoid HMBA of resulting purification, four (3- mercaptopropionic acid) pentaerythritol esters (lark prestige) 1
Mole and 0.7 mole of triallyl cyanurate be dissolved in 4mL DMF, be added photoinitiator 4-dimethylaminopyridine
DMAP, the additional amount of photoinitiator are the 1% of reaction system total weight, and stirring forms uniform solution at room temperature.Then with 0.22 μ
M filter is filtered solution, obtains pure crosslinked fluid.1ml crosslinked fluid is pipetted every time coated on substrate (glass plate) table
On face, in ultraviolet light intensity 15mW/cm2Irradiation is lower to carry out photocured cross-linked reaction 10min, and the substrate after solidification is placed in infrared lamp
Under, so that partial solvent DMF volatilizees.It is finally impregnated and is dried with solvent DMF to remove the raw material that coating surface does not react completely
And solvent, Capsaicinoid parents' network marine anti-pollution coating is finally obtained, parents' network nonpolluting coating containing Capsaicin is finally obtained,
Its photo is as shown in figure 3, parents' network coating is as shown in Figure 5 to the sterilizing rate situation of Escherichia coli.
The contact angle of marine anti-pollution coating produced by the present invention is 135 °, breaking strength 6MPa, and the swelling ratio in water is
1.5%, pencil hardness HB, adhesive force are 1 grade, and acidproof and weak base, BSA adsorbance is 26ug/cm2, can relative to PDMSe
85% is reduced, the adherency of diatom is 140x103n/cm2, relative to PDMSe, 88% is reduced, the adherency of stone mushroom spore is 180x103n/
cm2, relative to PDMSe, 75% is reduced, sterilizing rate reaches 78%, has splendid anti-fouling effect.
Embodiment 3
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 150 parts of ethyl alcohol, then 32.5 parts of guaiacol and 5 are added thereto
Part anhydrous magnesium sulfate, is placed in after stirring 30min in ice-water bath, and 10 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice after reaction 2 hours
Water-bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 5 days.After reaction, filtered on buchner funnel is used
Obtaining white precipitate is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the knot again are obtained by recrystallization
Brilliant specific steps are as follows: 40 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, the solution of filtering removal while hot
In impurity.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification,
It is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.5 mole of the Capsaicinoid HMBA, 1 mole of poly dimethyl sulfydryl siloxanes and poly- second two of resulting purification
0.5 mole of alcohol diacrylate is dissolved in 10mL DMF, and photoinitiator 4-dimethylaminopyridine DMAP is added, photoinitiator
Additional amount is the 0.5% of reaction system total weight, and stirring forms uniform solution at room temperature.Then with 0.22 μm of filter to solution
It is filtered, obtains pure crosslinked fluid.It pipettes 1ml crosslinked fluid every time to be coated on substrate (glass plate) surface, in ultraviolet light
Strong 20mW/cm2Irradiation is lower to carry out photocured cross-linked reaction 15min, and the substrate after solidification is placed under infrared lamp, so that part is molten
Agent DMF volatilization.It is finally impregnated and is dried with solvent DMF to remove the raw material and solvent that coating surface does not react completely, it is final to obtain
To Capsaicinoid parents' network marine anti-pollution coating, photo as shown in figure 3, parents' network coating to the sterilizing rates of Escherichia coli
Situation is as shown in Figure 5.
The contact angle of marine anti-pollution coating produced by the present invention is 140 °, breaking strength 10MPa, and the swelling ratio in water is
3.6%, pencil hardness 2H, adhesive force are 1 grade, and acidproof and weak base, BSA adsorbance is 10ug/cm2, can relative to PDMSe
98% is reduced, the adherency of diatom is 100x103n/cm2, relative to PDMSe, 93% is reduced, the adherency of stone mushroom spore is 150x103n/
cm2, relative to PDMSe, 83% is reduced, sterilizing rate reaches 81%, has splendid anti-fouling effect.
Embodiment 4
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 120 parts of ethyl alcohol, then 35 parts of guaiacol and 6 parts are added thereto
Anhydrous magnesium sulfate is placed in after stirring 1h in ice-water bath, and 15 parts of concentrated sulfuric acids are added dropwise dropwise and removes ice-water bath after reaction 2 hours and exists
Continuous heating stirs progress Friedel-Crafts reaction in 7 days in 35 DEG C of oil bath pans.After reaction, it is obtained with filtered on buchner funnel white
Color precipitating is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the tool of the recrystallization are obtained by recrystallization
Body step are as follows: 50 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, it is miscellaneous in the solution of filtering removal while hot
Matter.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification, is placed in
In vacuum drying oven after 35 DEG C of drying, it is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.7 mole of the Capsaicinoid HMBA, 1 mole of poly dimethyl sulfydryl siloxanes and poly- second two of resulting purification
0.3 mole of alcohol diacrylate is dissolved in 8mL DMF, and photoinitiator 4-dimethylaminopyridine DMAP is added, photoinitiator
Additional amount is the 0.8% of reaction system total weight, and stirring forms uniform solution at room temperature.Then with 0.22 μm of filter to solution
It is filtered, obtains pure crosslinked fluid.It pipettes 1ml crosslinked fluid every time to be coated on substrate (glass plate) surface, in ultraviolet light
Strong 25mW/cm2Irradiation under carry out photocured cross-linked reaction 15min, the substrate after solidification is placed under infrared lamp, so that part
Solvent DMF volatilization.It is finally impregnated and is dried with solvent DMF to remove the raw material and solvent that coating surface does not react completely, finally
Capsaicinoid parents' network marine anti-pollution coating is obtained, photo is as shown in figure 3, sterilization of parents' network coating to Escherichia coli
Rate situation is as shown in Figure 5.
The contact angle of marine anti-pollution coating produced by the present invention is 136 °, breaking strength 5MPa, and the swelling ratio in water is
4.3%, pencil hardness 3H, adhesive force are 1 grade, and acidproof and weak base, BSA adsorbance is 20ug/cm2, can relative to PDMSe
88% is reduced, the adherency of diatom is 120x103n/cm2, relative to PDMSe, 90% is reduced, the adherency of stone mushroom spore is 165x103n/
cm2, relative to PDMSe, 78% is reduced, there is splendid anti-fouling effect.
Embodiment 5
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 120 parts of ethyl alcohol, then thereto be added 42.5 parts of guaiacol and
10 parts of anhydrous magnesium sulfates are placed in after stirring 1.5h in ice-water bath, and 20 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice after reaction 2 hours
Water-bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 5 days.After reaction, filtered on buchner funnel is used
Obtaining white precipitate is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the knot again are obtained by recrystallization
Brilliant specific steps are as follows: 30 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, the solution of filtering removal while hot
In impurity.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification,
It is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.9 mole of the Capsaicinoid HMBA, 1 mole of poly dimethyl sulfydryl siloxanes and melamine of resulting purification
0.1 mole of sour triallyl is dissolved in 10mLDMF, and photoinitiator 4-dimethylaminopyridine DMAP is added, and photoinitiator adds
Enter 0.5% that amount is reaction system total weight, stirring forms uniform solution at room temperature.Then with 0.22 μm of filter to solution into
Row filtering, obtains pure crosslinked fluid.It pipettes 1ml crosslinked fluid every time to be coated on substrate (glass plate) surface, in ultraviolet light intensity
25mW/cm2Irradiation under carry out photocured cross-linked reaction 20min, the substrate after solidification is placed under infrared lamp, so that part is molten
Agent DMF volatilization.It is finally impregnated and is dried with solvent DMF to remove the raw material and solvent that coating surface does not react completely, it is final to obtain
To Capsaicinoid parents' network marine anti-pollution coating.
The contact angle of marine anti-pollution coating produced by the present invention is 138 °, breaking strength 8.5MPa, the swelling ratio in water
It is 5.1%, pencil hardness 1H, adhesive force is 0 grade, acidproof and weak base, and BSA adsorbance is 13ug/cm2, relative to PDMSe,
93% can be reduced, the adherency of diatom is 105x103n/cm2, relative to PDMSe, 92% is reduced, the adherency of stone mushroom spore is
155x103n/cm2, relative to PDMSe, 81% is reduced, sterilizing rate reaches 83%, has splendid anti-fouling effect.
Embodiment 6
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 120 parts of ethyl alcohol, then 50 parts of guaiacol and 8 parts are added thereto
Anhydrous magnesium sulfate is placed in after stirring 120min in ice-water bath, and 25 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice water after reaction 2 hours
Bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 7 days.After reaction, it is obtained with filtered on buchner funnel
Obtaining white precipitate is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the recrystallization are obtained by recrystallization
Specific steps are as follows: into Capsaicinoid crude product be added 20 parts of ethyl alcohol, be heated to being completely dissolved, while hot filtering removal solution in
Impurity.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification, puts
After being placed in vacuum drying oven 35 DEG C of drying, it is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By HMBA0.8 moles of the Capsaicinoid of resulting purification, 1 mole of four (3- mercaptopropionic acid) pentaerythritol ester and three
0.2 mole of paracyanogen acid triallyl is dissolved in 12mL DMF, and photoinitiator 4-dimethylaminopyridine DMAP, photoinitiator is added
Additional amount be reaction system total weight 0.7%, at room temperature stirring form uniform solution.Then with 0.22 μm of filter to molten
Liquid is filtered, and obtains pure crosslinked fluid.It pipettes 1ml crosslinked fluid every time to be coated on substrate (glass plate) surface, ultraviolet
Light intensity 15mW/cm2Irradiation under carry out curing cross-linking reaction 30min under light, the substrate after solidification is placed under infrared lamp so that
Partial solvent DMF volatilization.It is finally impregnated and is dried with solvent DMF to remove the raw material and solvent that coating surface does not react completely,
Finally obtain Capsaicinoid parents' network marine anti-pollution coating.
The contact angle of marine anti-pollution coating produced by the present invention is 135 °, breaking strength 9.3MPa, the swelling ratio in water
It is 2.5%, hardness 3H, adhesive force is 1 grade, acidproof and weak base, and BSA adsorbance is 11ug/cm2, relative to PDMSe, can subtract
Few 95%, the adherency of diatom is 120x103n/cm2, relative to PDMSe, 90% is reduced, the adherency of stone mushroom spore is 190x103n/
cm2, relative to PDMSe, 73% is reduced, sterilizing rate reaches 93%, has splendid anti-fouling effect.
Embodiment 7
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 200 parts of ethyl alcohol, then 60 parts of guaiacol and 12 are added thereto
Part anhydrous magnesium sulfate, is placed in after stirring 120min in ice-water bath, and 20 parts of concentrated sulfuric acids are added dropwise dropwise and remove ice after reaction 2 hours
Water-bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 7 days.After reaction, filtered on buchner funnel is used
Obtaining white precipitate is Capsaicinoid (HMBA) crude product.The Capsaicinoid of purification, the knot again are obtained by recrystallization
Brilliant specific steps are as follows: 50 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, the solution of filtering removal while hot
In impurity.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered the HMBA for obtaining purification,
It is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.6 mole of the Capsaicinoid HMBA of resulting purification, 1 mole of trimethylolpropane tris (3-thiopropionate)
And 0.4 mole of polyethyleneglycol diacrylate be dissolved in 8mLDMF, and photoinitiator 4-dimethylaminopyridine DMAP, light is added
The additional amount of initiator is the 0.4% of reaction system total weight, and stirring forms uniform solution at room temperature.Then it is filtered with 0.22 μm
Device is filtered solution, obtains pure crosslinked fluid.1ml crosslinked fluid is pipetted every time to be coated on substrate (glass plate) surface,
In ultraviolet light intensity 20mW/cm2Irradiation under carry out curing cross-linking reaction 15min under light, the substrate after solidification is placed in infrared lamp
Under, so that partial solvent DMF volatilizees.It is finally impregnated and is dried with solvent DMF to remove the raw material that coating surface does not react completely
And solvent, finally obtain Capsaicinoid parents' network marine anti-pollution coating.
The contact angle of marine anti-pollution coating produced by the present invention is 135 °, breaking strength 9.3MPa, the swelling ratio in water
It is 2.5%, pencil hardness 3H, adhesive force is 1 grade, acidproof and weak base, and BSA adsorbance is 11ug/cm2, relative to PDMSe,
95% can be reduced, the adherency of diatom is 120x103n/cm2, relative to PDMSe, 90% is reduced, the adherency of stone mushroom spore is
190x103n/cm2, relative to PDMSe, 73% is reduced, sterilizing rate reaches 88%, has splendid anti-fouling effect.
Embodiment 8
A kind of preparation method of Capsaicinoid parents network marine anti-pollution coating, specific steps are as follows:
1, Friedel-Crafts reaction is carried out using guaiacol and unsaturated amides obtain Capsaicinoid structures alone:
10 parts of N hydroxymethyl acrylamides are dissolved in 250 parts of ethyl alcohol, then thereto be added 62.5 parts of guaiacol and
12 parts of anhydrous magnesium sulfates are placed in after stirring 60min in ice-water bath, and 25 parts of concentrated sulfuric acids are added dropwise dropwise and remove after reaction 2 hours
Ice-water bath continuous heating in 35 DEG C of oil bath pans stirs progress Friedel-Crafts reaction in 7 days.After reaction, with Buchner funnel mistake
It is Capsaicinoid (HMBA) crude product that filter, which obtains white precipitate,.The Capsaicinoid of purification, the weight are obtained by recrystallization
The specific steps of crystallization are as follows: 50 parts of ethyl alcohol are added into Capsaicinoid crude product, are heated to being completely dissolved, filtering removal while hot is molten
Impurity in liquid.Filtrate stands and slowly cools down, and after being precipitated in filtrate there is no crystallization, then is filtered and obtains purification
HMBA is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator stand-by.
2, resulting Capsaicinoid structures alone is drawn with unsaturated multi-functional crosslinking agent and mercaptothiols through light
Hair crosslinking:
By 0.4 mole of the Capsaicinoid HMBA of resulting purification, 1 mole of trimethylolpropane tris (3-thiopropionate)
And 0.6 mole of polyethyleneglycol diacrylate be dissolved in 12mL DMF, and photoinitiator 4-dimethylaminopyridine DMAP is added,
The additional amount of photoinitiator be reaction system total weight 0.9%, after at room temperature stirring form uniform solution.Then with 0.22 μm
Filter is filtered solution, obtains pure crosslinked fluid.1ml crosslinked fluid is pipetted every time coated on substrate (glass plate) surface
On, in ultraviolet light intensity 20mW/cm2Irradiation under carry out photocured cross-linked reaction 15min, the substrate after solidification is placed in infrared lamp
Under, so that partial solvent DMF volatilizees.It is finally impregnated and is dried with solvent DMF to remove the raw material that coating surface does not react completely
And solvent, finally obtain Capsaicinoid parents' network marine anti-pollution coating.
The contact angle of marine anti-pollution coating produced by the present invention is 139 °, breaking strength 9.1MPa, the swelling ratio in water
It is 5%, pencil hardness 2H, adhesive force is 0 grade, acidproof and weak base, and BSA adsorbance is 10.5ug/cm2, relative to PDMSe,
97% can be reduced, the adherency of diatom is 105x103n/cm2, relative to PDMSe, 92% is reduced, the adherency of stone mushroom spore is
115x103n/cm2, relative to PDMSe, 81% is reduced, sterilizing rate reaches 90%, has splendid anti-fouling effect.Fig. 4 is blank
About BSA, the desorption of diatom, stone mushroom tests histogram for glass plate and 8 floating coat of embodiment.
It should be understood that after reading the content taught by the present invention, those skilled in the art can make the present invention various
Change or modification, these equivalent forms also fall within the scope of the appended claims of the present application.
Claims (10)
1. a kind of preparation method of Capsaicinoid parents network marine anti-pollution coating characterized by comprising utilize guaiacol
Friedel-Crafts reaction, which is carried out, with unsaturated amides obtains Capsaicinoid structures alone；By resulting Capsaicinoid structures alone with
Unsaturated multi-functional crosslinking agent and mercaptothiols obtain Capsaicinoid parents' network marine anti-pollution through photo-initiated crosslinking and apply
Layer.
2. the preparation method of Capsaicinoid parents network marine anti-pollution coating as described in claim 1, which is characterized in that described
Unsaturated amides be N hydroxymethyl acrylamide or hydroxyethyl acrylamide class monomer.
3. the preparation method of Capsaicinoid parents network marine anti-pollution coating as described in claim 1, which is characterized in that described
Mercaptothiols be poly dimethyl sulfydryl siloxanes, trimethylolpropane tris (3-thiopropionate), trimethylolpropane tris (2-
At least one of mercaptoacetate) and four (3- mercaptopropionic acid) pentaerythritol esters.
4. the preparation method of Capsaicinoid parents network marine anti-pollution coating as described in claim 1, which is characterized in that described
The multi-functional crosslinking agent of unsaturation be at least one of polyethyleneglycol diacrylate and triallyl cyanurate.
5. the preparation method of Capsaicinoid parents network marine anti-pollution coating as described in claim 1, which is characterized in that described
Carry out the specific steps packet that Friedel-Crafts reaction obtains Capsaicinoid structures alone using guaiacol and unsaturated amides
It includes: unsaturated amides is dissolved in solvent A, then guaiacol and deicer are added thereto, be placed in ice-water bath and stir
After 30-60min, catalyst is added dropwise dropwise and removes ice-water bath, the continuous heating in 35-60 DEG C of oil bath pan after reaction 2-10 hours
Progress Friedel-Crafts reaction in 3-7 days is stirred, after reaction, obtaining white precipitate with filtered on buchner funnel is Capsaicinoid
Crude product；Wherein, unsaturated amides, guaiacol, deicer, catalyst, solvent A weight ratio be 10:12.5-62.5:
2.4-12:5-25:50-250.
6. the preparation method of Capsaicinoid parents network marine anti-pollution coating as claimed in claim 5, which is characterized in that described
Carry out Friedel-Crafts reaction using guaiacol and unsaturated amides and obtain the specific steps of Capsaicinoid structures alone also
It include: the Capsaicinoid that purification is obtained by recrystallization；The specific steps of the recrystallization include: to Capsaicinoid crude product
Middle addition solvent A, is heated to being completely dissolved, while hot filtering removal solution in impurity, filtrate stand cooling, in filtrate no longer
After thering is crystallization to be precipitated, then it is filtered the Capsaicinoid for obtaining purification, is placed in vacuum drying oven after 35 DEG C of drying, is placed in refrigerator
In it is stand-by.
7. the preparation method of Capsaicinoid parents network marine anti-pollution coating as described in claim 1, which is characterized in that described
Resulting Capsaicinoid structures alone is obtained with unsaturated multi-functional crosslinking agent and mercaptothiols through photo-initiated crosslinking
Specific steps to Capsaicinoid parents' network marine anti-pollution coating include: that Capsaicinoid and mercaptothiols and unsaturation are more
The crosslinking agent of functional group is dissolved in solvent B, is added after photoinitiator stirring at room temperature and is formed uniform solution, then to solution
Be filtered, obtain crosslinked fluid, pipette a certain amount of crosslinked fluid coated on substrate surface, irradiate under ultraviolet light 5-20min into
Row photocuring, the substrate after solidification are placed under infrared lamp so that partial solvent B volatilize, finally impregnated and dried with solvent B with
Raw material and solvent B that coating surface does not react completely are removed, Capsaicinoid parents' network marine anti-pollution coating is obtained.
8. prepared by the preparation method of Capsaicinoid parents network marine anti-pollution coating of any of claims 1-7
Capsaicinoid parents' network marine anti-pollution coating.
9. Capsaicinoid parents network marine anti-pollution coating as claimed in claim 8, which is characterized in that its contact angle is 130-
140 °, breaking strength reaches 4-10MPa, and swellbility in water is 0.5%-5.1%, pencil hardness 3B-5H, and adhesive force is
0-1 grades.
10. Capsaicinoid prepared by the preparation method of Capsaicinoid parents network marine anti-pollution coating described in claim 1
Parents' network marine anti-pollution coating is as the application in coating for watercraft, underwater equipment nonpolluting coating.
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| CN1398410A (en) * | 1998-05-07 | 2003-02-19 | Dsm有限公司 | Dielectric radiation-curable coating compsns. |
| CN1616560A (en) * | 2004-10-12 | 2005-05-18 | 朱松年 | Environment protection anti-foulant material and anti-fouling paint |
| CN103951578A (en) * | 2014-05-06 | 2014-07-30 | 中国海洋大学 | Multifunctional acrylamide compound containing capsaicin-like functional structure and preparation method and application thereof |
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