CN109517132A - A kind of compound and preparation method thereof with anti-pollution - Google Patents
A kind of compound and preparation method thereof with anti-pollution Download PDFInfo
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- CN109517132A CN109517132A CN201710846702.5A CN201710846702A CN109517132A CN 109517132 A CN109517132 A CN 109517132A CN 201710846702 A CN201710846702 A CN 201710846702A CN 109517132 A CN109517132 A CN 109517132A
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/71—Monoisocyanates or monoisothiocyanates
- C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/48—Polyethers
- C08G18/50—Polyethers having heteroatoms other than oxygen
- C08G18/5003—Polyethers having heteroatoms other than oxygen having halogens
- C08G18/5015—Polyethers having heteroatoms other than oxygen having halogens having fluorine atoms
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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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/336—Polymers modified by chemical after-treatment with organic compounds containing silicon
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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
- C09D5/1606—Antifouling paints; Underwater paints characterised by the anti-fouling agent
- C09D5/1637—Macromolecular compounds
Abstract
The present invention relates to a kind of compound with anti-pollution, are as follows: PFPE (CH2OCONCH2CH2CH2Si(OR)3)2；PFPE is-(CF2O)x‑(CF2CF2O)y, R is methyl or ethyl.The compound of the present invention, which passes through, tests after it forms a film on glass slide to the contact angle of water up to 114 °；To the contact angle of hexadecane up to 72 °, belongs to waterproof, refuses light wood material.Meanwhile the glass slide after the film forming can be rubbed 10000 times with steel wool under 1kg load and significantly reduce its waterproof, oil repellency, therefore have excellent rub resistance.By the test of dynamic friction coefficient, dynamic friction coefficient has reached 0.03, and smoothness has reached world level, is also with a wide range of applications in other advanced optical devices fields.
Description
Technical field
The present invention relates to touch screen surface soilings to contaminate object technical field, and in particular to a kind of chemical combination with anti-pollution
Object.
Background technique
3C industry, tempered glass, handset touch panel, digital camera touch screen, flat-panel monitor, optical glass lens, clock
Due to often touching, frequency of use is higher on the surfaces such as table, office equipment, tends to by fingerprint, sweat, grease, and smears
Cosmetics polluted, and easily by hard object institute scratching.Have that the surface of anti-reflection coating is very sensitive to dirt, fingerprint etc., one
Denier, which is contaminated, often influences beautiful and using effect, while the cleaning of these dirts is difficult, needs specially treated that could restore to manage
The state thought.Especially in requiring harsh application, such as hand-held electronic equipment and display, institute's facing challenges are to obtain
The surface of one resistance to dirt with long-term wear properties.A kind of current effective solution route is to carry out fluorination to material to change
Property, further decrease material surface can, improve the performances such as the oil resistant of material, solvent resistant, antifouling.With the development of science and technology, very
Polyelectron industry field can all apply relevant technology, and wherein the processing of glass surface is most widely used.It would therefore be highly desirable to develop
It is a kind of efficiently, environmental protection, low-temp reaction type, low surface tension fluorinated modified nanometer coating material, so as to improve glass devices
Hydrophobic, the oil repellent on surface, the effective function of improving contact angle and reduce coefficient of friction, reach waterproof, refuse oil, is resistant to pollution
Effect.Perfluorochemical and fluorine-free compounds response characteristic differ greatly, it is difficult to are bonded together by conventional method.Cause
This is difficult firmly for fluorine material to be distributed in the surface of these floride-free materials, and thus we, which are badly in need of searching some way, makes two
Person closely combines, and meets waterproof, refuses oil, antipollution requirement.
In recent years, organic fluorinated silicone modified to become a very active research field.Currently, antifouling used in the country
Stain is often similar to perfluoro caprylic acid (PFOA) and its esters and this kind of perfluoroalkyl class compound of derivative, this kind of compound
It is listed in persistence organic pollutant, does not have environment friendly, to accelerate China to fulfil the process of " Convention of Stockholm ",
The health of environment and the people is protected, environmental-friendly antistain agent is badly in need of developing to substitute current product in China.
Currently, domestic also relatively backward in fluorine silicon antistain agent field, domestic mainstream made products often more low side is high
The waterproof oil-repellent agent at end is mainly from a few developed country's import.At present both at home and abroad for waterproof oil-repellent agent document report compared with
It is few, urethane acrylate has been used in patent US20040181008, CN102408434, prepares perfluoropolyether-modified gather
Urethane acyclic compound.Lekai company reports the Soviet Union for using molecular weight to be 700~1200 in patent CN102408434
Prestige D series perfluoropolyether alcohol is raw material, and final product structure is as follows:
Big King Company reports that using Demnum series perfluoropolyether alcohol is raw material in patent US20040181008,
Its molecular weight is 2000 or so, and final goal product structure is as follows:
Above-mentioned patent has used environmental-friendly perfluoropolyether compound as raw material, however does not introduce siliceous
" bridge " group, therefore be not easy to adhere in glass surface；Further, since the introducing of multiple amide groups is so that synthesize such chemical combination
Object needs considerable step, and purifies and separates post-processing is difficult, so that cost is high, limits its application.
Summary of the invention
The object of the present invention is to provide a kind of ideal compound of preventing polluting effect, are as follows: PFPE (CH2OCONCH2CH2CH2Si(OR)3)2；PFPE is-(CF2O)x-(CF2CF2O)y, R is methyl or ethyl；The x is 0~63, and/or, the y is 0
~36.
PFPE can be-CF2O-, or be-CF2CF2O-, i.e., also belonging to the application there is only a kind of the case where group will protect
Range, but x, y are not simultaneously 0.
Preferably, the relative molecular weight of the PFPE is 4000~4400, more preferably 4100~4300.
Most preferably, the compound of the present invention is PFPE (CH2OCONCH2CH2CH2Si(OR)3)2；PFPE is-(CF2O)x-
(CF2CF2O)y, it is methyl or ethyl that the relative molecular weight of the PFPE, which is 4160, R,.It is 4000 in the relative molecular weight of PFPE
In~4400 ranges, compound all has good performance, but discovery is when the relative molecular weight of PFPE is 4160 in testing
Effect is more preferable.
It is a further object of the present invention to provide the preparation methods of this compound, include the following steps: HOCH2PFPECH2OH
With 3- isocyanate group propyl trialkoxy silane under the action of condensing agent it is prepared by condensation reaction to it is described have it is antifouling
The compound of dye effect；PFPE is-(CF2O)x-(CF2CF2O)y, the x is 0~63, and the y is 0~36, and reaction equation is such as
Under:
In real reaction, PFPE can be-CF2O-, or be-CF2CF2A kind of the case where O-, i.e., there is only groups, also can be real
It now reacts, but x, y are not simultaneously 0.
Preferably, the 3- isocyanate group propyl trialkoxy silane is 3- isocyanate group propyl trimethoxy silicane
Or 3- isocyanate group propyl-triethoxysilicane.
Preferably, the HOCH2PFPECH2The molecular weight of OH is 4000~4400.
It is further preferred that the HOCH2PFPECH2The molecular weight of OH is 4100~4300.
It is furthermore preferred that the relative molecular weight of the PFPE is 4160.
Preferably, the HOCH2PFPECH2The molar ratio of OH and 3- isocyanate group propyl trialkoxy silane be 1:1~
3。
Preferably, the condensing agent is dibutyl tin dilaurate.The study found that dibutyl tin dilaurate can not only rise
To effective catalytic action, and itself has the excellent transparency, and lubricity will not have an impact the quality of product,
And other catalyst may the indices such as yield, contact angle, slipping to product generate certain influence.
Preferably, the HOCH2PFPECH2OH and 3- isocyanate group propyl trialkoxy silane has hydrofluoroether class
It is reacted in solvent.
Preferably, the hydrofluoroether class organic solvent needs fully dissolve reactant, is also easy to volatilize.Actually answering
May be selected during the production of 3M company 7200, HFE374 or HFE347, wherein more with 7200 effects of 3M company production
It is good.
Preferably, the HOCH2PFPECH2OH and 3- isocyanate group propyl trialkoxy silane is taken the photograph in temperature 50~70
It is reacted under the oxygen free condition of family name's degree；Preferably, reaction effect is more preferable under conditions of 60 degrees Celsius.
Preferably, the method for the present invention includes following steps:
1) in the reactor of anaerobic, HOCH is first added2PFPECH2OH adds fluorine-containing organic solvent and is dissolved, so
3- isocyanate group propyl trialkoxy silane is added dropwise afterwards, the examination of condensing agent dibutyl tin dilaurate is added dropwise again after mixing evenly
Agent；
2) reactor is warming up to 50-70 degrees Celsius, starts to react, carry out IR detection, until the infrared spectrum of detection
After upper 3369 completely disappear, it is further continued for 0.8~2h of reaction, obtains the compound with anti-pollution.
It is further preferred, the step 2) specifically: reactor is warming up to 50-70 degrees Celsius, starts to react laggard
Whether row IR detection is disappeared and whether 1235,1380 have signal appearance with detecting on infrared spectrum 3369, is disappeared completely to 3369
Reaction 1 hour is further continued for after mistake.Vacuum distillation removes the fluorine-containing organic solvent of low boiling point and raw material 3- isocyanate group propyl three
Alkoxy silane.Then crude product and multiple with n-hexane cleaning product, obtaining is filtered and final with 0.22um filter plate
Obtain target product.
It is furthermore preferred that the method for the present invention includes following steps:
1) in the reactor of anaerobic, HOCH is first added2PFPECH2OH, add the 7200 of fluorine-containing organic solvent 3M by its
Then 3- isocyanate group propyl trimethoxy silicane or 3- isocyanate group propyl-triethoxysilicane, stirring is added dropwise in dissolution
Condensing agent dibutyl tin dilaurate reagent, the HOCH are added dropwise again after uniformly2PFPECH2PFPE is-(CF in OH2O)x-
(CF2CF2O)y, relative molecular weight 4160, HOCH2PFPECH2OH and 3- isocyanate group propyl trimethoxy silicane or 3-
The ratio between amount of substance of isocyanate group propyl-triethoxysilicane is 1:1~3；
2) reactor is warming up to 50-70 degrees Celsius, starts to react, carry out IR detection, until the infrared spectrum of detection
After upper 3369 completely disappear, it is further continued for 0.8~2h of reaction, obtains the compound with anti-pollution.
Final object of the present invention is to protect the compound of the application in the application of Antipollution method, it is preferred that can
It is prepared into antifouling dye liquor, is coated on tempered glass, various touch screens and display, the surfaces such as optical glass lens.
Method of the invention has the following beneficial effects:
1) the compound of the present invention is easy to be coated on tempered glass, various touch screens and display, the tables such as optical glass lens
Face, plays the role of antipollution, and in tentative application, after it is dissolved with organic solvent, direct spraying is in above-mentioned material
Surface can be effectively adhere to the surface of glass by conventional activation processing；
By test, the preferable compound of effect of the invention form a film on glass slide after to the contact angle of water up to 114 °；
To the contact angle of hexadecane up to 72 °, belongs to waterproof, refuses light wood material.Meanwhile the glass slide after the film forming can be loaded in 1kg
It is lower with steel wool rub 10000 times and significantly reduce its waterproof, oil repellency, therefore have excellent rub resistance.Pass through
The test of dynamic friction coefficient, dynamic friction coefficient have reached 0.03, since carbamate groups and molecular weight are 4000 or so
The introducing of double hydroxy-end capped perfluoropolyether compounds, the smoothness for making it form a film obviously increase, while more environmentally friendly, push away
It is surveyed similarly to be with a wide range of applications in other advanced optical devices fields.
2) method of the invention only needs single step reaction, quickly, it is simple, efficiently, it is accurate, greenly synthesize a kind of novel environment friendly
Type fluorine silicon antistain agent realizes the fluorine-containing and quick perfect combination of material, and the two is made to have complementary advantages, bring out the best in each other.
3) one-step method shortens the reaction time greatly, and no coupling product generates, more atom economy, compared with similar products
It is more suitable for industrialized production.
4) characterizing method of the related applications indexs such as contact angle, rub resistance number, smoothness is provided.
Specific embodiment
The following examples are used to illustrate the present invention, but are not intended to limit the scope of the present invention..Involved in embodiment
HOCH2PFPECH2The relative molecular weight of PFPE is 4160 in OH, and the progress of reaction is illustrated as example.
Embodiment 1
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (1mol) (HOCH2PFPECH2OH), the dissolution of 7200 fluoride solvent of 400g 3M is added, then in room temperature item
6.15g 3- isocyanate group propyl trimethoxy silicane (1.5mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai；
2) 50 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl trimethoxy silicane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the trimethoxy silicon substrate propyl of 78.1g target product
Carbamate groups) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OMe)3)2.Yield is 92.7%.
Embodiment 2
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (HOCH2PFPECH2OH) (1mol), add 7200 fluoride solvent of 400g 3M dissolution, then in room temperature item
8.2g 3- isocyanate group propyl trimethoxy silicane (2.0mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai；
2) 50 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl trimethoxy silicane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the trimethoxy silicon substrate propyl of 79.3g target product
Carbamate groups) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OMe)3)2.Yield is 94.3%.
Embodiment 3
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (HOCH2PFPECH2OH) (1mol), add 7200 fluoride solvent of 400g 3M dissolution, then in room temperature item
10.3g 3- isocyanate group propyl trimethoxy silicane (2.5mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai；
2) 50 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl trimethoxy silicane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the trimethoxy silicon substrate propyl of 79.5g target product
Carbamate groups) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OMe)3)2.Yield is 94.5%.
Embodiment 4
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (HOCH2PFPECH2OH) (1mol), add 7200 fluoride solvent of 400g 3M dissolution, then in room temperature item
8.2g 3- isocyanate group propyl trimethoxy silicane (2.0mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai.
2) 60 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl trimethoxy silicane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the trimethoxy silicon substrate propyl of 81.7g target product
Carbamate groups) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OMe)3)2.Yield is 97.1%.
Embodiment 5
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (HOCH2PFPECH2OH) (1mol), add 7200 fluoride solvent of 400g 3M dissolution, then in room temperature item
8.2g 3- isocyanate group propyl trimethoxy silicane (2.0mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai.
2) 70 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl trialkoxy silane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the trimethoxy silicon substrate propyl of 80.4g target product
Carbamate groups) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OMe)3)2.Yield is 95.6%.
Embodiment 6
The present embodiment is related to a kind of preparation method of antipollution compound, includes the following steps:
1) it under the conditions of anhydrous and oxygen-free, is first added in the 1L three-necked flask equipped with blender, condenser pipe and dropping funel
80g perfluoropolyether (HOCH2PFPECH2OH) (1mol), add 7200 fluoride solvent of 400g 3M dissolution, then in room temperature item
9.9g 3- isocyanate group propyl-triethoxysilicane (2.0mol) is slowly added dropwise by dropping funel under part, stirs several points
4 drops condensing agent dibutyl tin dilaurate reagent (DBTDL) are added dropwise in Zhong Houzai.
2) 60 degrees Celsius of reactions are warming up to and per half an hour carries out IR detection, with detect on infrared spectrum 3369 whether
It disappears and whether 1235,1380 has signal appearance, reaction 1 hour is further continued for after 3369 completely disappear.Vacuum distillation removes
7200 fluoride solvent of low boiling point 3M and raw material 3- isocyanate group propyl-triethoxysilicane are simultaneously more with n-hexane cleaning product
It is secondary.Obtained crude product is filtered with 0.22um filter plate and finally obtains bis- (the triethoxy silicon substrate propyl of 81.8g target product
Amion acetic acid ester group) perfluoropolyether PFPE (CH2OCONCH2CH2CH2Si(OEt)3)2.Yield is 96.3%.
Performance test
It is 3/1000ths that the antistain agent of the application, which is diluted to mass concentration with 7200 fluoride solvent of 3M, is sprayed at glass
Glass panel surface, and its correlated performance is tested after being activated.Its related hydrophobic refuses oily data and is shown in Table 1.
The performance test of 1 fluorine silicon antistain agent of table
Above-mentioned glass panel is added into 1kg weight, using steel wool, its crocking resistance is tested by abrasion machine, summary is shown in
Table 2.
The test of 2 rub resistance number of table
By above-mentioned glass panel by dynamic friction coefficient analyzer, its smooth performance is tested.Summary is shown in Table 3.
The test of 3 dynamic friction coefficient of table
In conclusion the antistain agent obtained using this method, performance is very excellent, and (water contact angle reaches index of correlation
114 °, hexadecane contact angle is up to 72 °；Rub resistance number reaches 10000 or more；0.03) dynamic friction coefficient is down to having reached
The leading level in the world.
Although above having used general explanation, specific embodiment and test, the present invention is made to retouch in detail
It states, but on the basis of the present invention, it can be made some modifications or improvements, this is apparent to those skilled in the art
's.Therefore, these modifications or improvements without departing from theon the basis of the spirit of the present invention, belong to claimed
Range.
Claims (10)
1. a kind of compound with anti-pollution, are as follows: PFPE (CH2OCONCH2CH2CH2Si(OR)3)2；PFPE be-
(CF2O)x-(CF2CF2O)y, R is methyl or ethyl；The x is 0~63, and/or, the y is 0~36.
2. compound according to claim 1 or 2, which is characterized in that the relative molecular weight of the PFPE be 4000~
4400。
3. a kind of preparation method of the compound with anti-pollution, which is characterized in that HOCH2PFPECH2OH and 3- isocyanide
Perester radical propyl trialkoxy silane obtains the chemical combination with anti-pollution through condensation reaction under the action of condensing agent
Object；PFPE is-(CF2O)x-(CF2CF2O)y, the x is 0~63, and/or, the y is 0~36.
4. according to the method described in claim 3, it is characterized in that, the 3- isocyanate group propyl trialkoxy silane is 3-
Isocyanate group propyl trimethoxy silicane or 3- isocyanate group propyl-triethoxysilicane；
And/or the HOCH2PFPECH2The molecular weight of OH is 4000~4400；
And/or the HOCH2PFPECH2The molar ratio of OH and 3- isocyanate group propyl trialkoxy silane is 1:1~3.
5. the method according to claim 3 or 4, which is characterized in that the condensing agent is dibutyl tin dilaurate.
6. the method according to claim 3 or 5, which is characterized in that the HOCH2PFPECH2OH and 3- isocyanate group third
Base trialkoxy silane is reacted in the organic solvent of hydrofluoroether class.
7. the method according to claim 3 or 6, which is characterized in that the HOCH2PFPECH2OH and 3- isocyanate group third
Base trialkoxy silane is reacted under 50~70 degrees Celsius of temperature of oxygen free condition.
8. according to the described in any item methods of claim 3~7, which comprises the steps of:
1) in the reactor of anaerobic, HOCH is first added2PFPECH2OH, the organic solvent for adding hydrofluoroether class are dissolved,
Then 3- isocyanate group propyl trialkoxy silane is added dropwise, the examination of condensing agent dibutyl tin dilaurate is added dropwise again after mixing evenly
Agent；
2) reactor is warming up to 50-70 degrees Celsius, starts to react, carry out IR detection, until on the infrared spectrum of detection
After 3369 completely disappear, it is further continued for 0.8~2h of reaction, obtains the compound with anti-pollution.
9. claims 1 or 2 and claim 3~8 compound are in the application of anti-pollution aspect.
10. application according to claim 10, which is characterized in that the compound is being prepared into antifouling dye liquor.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN110452307A (en) * | 2019-07-24 | 2019-11-15 | 衢州学院 | A kind of modified nanometer cellulose and preparation method thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
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