CN106432686B - A kind of novel perfluoropolyether alkoxysilane compound and its synthetic method - Google Patents
A kind of novel perfluoropolyether alkoxysilane compound and its synthetic method Download PDFInfo
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- 239000010702 perfluoropolyether Substances 0.000 title claims abstract description 42
- 150000001875 compounds Chemical class 0.000 title claims abstract description 22
- 238000010189 synthetic method Methods 0.000 title claims abstract description 12
- 238000006243 chemical reaction Methods 0.000 claims abstract description 33
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 22
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 claims abstract description 17
- 239000002904 solvent Substances 0.000 claims abstract description 17
- YXRKNIZYMIXSAD-UHFFFAOYSA-N 1,6-diisocyanatohexane Chemical compound O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O.O=C=NCCCCCCN=C=O YXRKNIZYMIXSAD-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000010790 dilution Methods 0.000 claims abstract description 9
- 239000012895 dilution Substances 0.000 claims abstract description 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 7
- 239000004593 Epoxy Substances 0.000 claims abstract description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims abstract description 4
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
- 239000001301 oxygen Substances 0.000 claims abstract description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims abstract description 4
- 229910052731 fluorine Inorganic materials 0.000 claims description 14
- 239000011737 fluorine Substances 0.000 claims description 14
- 238000003756 stirring Methods 0.000 claims description 14
- 238000009413 insulation Methods 0.000 claims description 13
- 239000004210 ether based solvent Substances 0.000 claims description 9
- 239000000203 mixture Substances 0.000 claims description 8
- 238000007865 diluting Methods 0.000 claims description 3
- 125000001153 fluoro group Chemical group F* 0.000 claims description 3
- 239000000126 substance Substances 0.000 claims description 2
- 239000002243 precursor Substances 0.000 claims 1
- 239000000376 reactant Substances 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- 239000011521 glass Substances 0.000 abstract description 14
- 239000000758 substrate Substances 0.000 abstract description 11
- 230000003666 anti-fingerprint Effects 0.000 abstract description 10
- 230000006837 decompression Effects 0.000 abstract description 7
- -1 perfluoro Chemical group 0.000 abstract description 7
- 229910000077 silane Inorganic materials 0.000 abstract description 5
- 239000010408 film Substances 0.000 abstract description 3
- 239000004033 plastic Substances 0.000 abstract description 3
- 229920003023 plastic Polymers 0.000 abstract description 3
- 238000007711 solidification Methods 0.000 abstract description 3
- 230000008023 solidification Effects 0.000 abstract description 3
- 238000005299 abrasion Methods 0.000 abstract 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 230000015572 biosynthetic process Effects 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 6
- 238000013019 agitation Methods 0.000 description 5
- 230000003373 anti-fouling effect Effects 0.000 description 5
- 238000004090 dissolution Methods 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920001296 polysiloxane Polymers 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 239000003921 oil Substances 0.000 description 4
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 230000002194 synthesizing effect Effects 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000007639 printing Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000003670 easy-to-clean Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- ZHPNWZCWUUJAJC-UHFFFAOYSA-N fluorosilicon Chemical compound [Si]F ZHPNWZCWUUJAJC-UHFFFAOYSA-N 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
Classifications
-
- 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
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
- C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3893—Low-molecular-weight compounds having heteroatoms other than oxygen 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
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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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
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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
- C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
- C09D175/04—Polyurethanes
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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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- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
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- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Polyethers (AREA)
Abstract
The invention discloses a kind of novel perfluoro polyetheralkoxy silane compound and its synthetic methods, shown in compound structure such as formula (1), its synthetic method is as follows: terminal hydroxy group perfluoropolyether (PFPE), 3- (2- amino-ethyl) TSL 8330, 3- (2, the third oxygen of 3- epoxy) propyl trimethoxy silicane (KH560), 1:2:2:1 reacts HDI trimer in molar ratio, using a certain amount of solvent dilution mixing terminal hydroxy group perfluoropolyether in reaction process, it is added dropwise to HDI trimer again after 3- (2- amino-ethyl) TSL 8330, after being reacted 6 hours under certain temperature, KH560 is added dropwise again, decompression removal solvent is after reacting again under certain temperature 6 hours up to novel perfluoropolyether alkoxysilane compound of the invention.The compound can be coated on the substrate surfaces such as glass, plastics, film, and crosslinked solidification forms one layer of firm film, assign substrate excellent anti-fingerprint anti-pollution, and high abrasion resistance.
Description
Technical field
The invention belongs to fluorine silicon technical field of novel materials, and in particular to one kind passes through terminal hydroxy group perfluoropolyether, 3- (2- ammonia
Base ethyl) TSL 8330, KH560, HDI trimer reaction synthesizing new anti-fingerprint, antifouling perfluoropolyether
Alkoxy silane, and be applied to the substrate surfaces such as glass formation film and excellent anti-fingerprint anti-pollution and wearability are provided.
Background technique
In recent years, using the display of mobile phone as representative, the touch panelization of screen is being accelerated.But touch panel is naked
The state of dew makes it be easy to be polluted by finger mark, skin oil and fat, sweat, cosmetics etc. in use, influences its appearance and use.Cause
This is in order to improve appearance and identity, for making the surfaces such as display, touch screen easily remove the technical requirements of dirt, anti-fingerprint
It is higher and higher, not only to assign touch panel surface good waterproof and oilproof stain-proofing layer, it is easy to clean, and its table in wiping
Face is not allowed to easily cause damage, to have good wear-resisting property, keeps long-term antifouling fingerprint resistance energy.
It is above desired in order to achieve the effect that, it has been disclosed introduce perfluoropolyether in alkoxysilane compound containing trialkylsilyl group in molecular structure at present
Group to improve anti-pollution (water and oil-resistant), this mainly use silane coupled technology, using alkoxysilane groups with
Moisture in air reacts, and forms silicone hydroxyl, and silicone hydroxyl under conditions of catalyst or high temperature with the substrates table such as glass
The silicone hydroxyl in face is condensed, and forms firm chemical bond, forms perfluoropolyether coating in glass surface.But these compound alcoxyls
Base silane group numbers ratio is less, can not provide enough adhesiveness, wearability and durability with substrate surfaces such as glass, with
Using the time extension, anti-pollution can be worse and worse.
Summary of the invention
Above-mentioned technical problem present in present invention aims to solve the prior art provides a kind of perfluoropolyether alkoxy
Silane compound and its synthetic method, by terminal hydroxy group perfluoropolyether, 3- (2- amino-ethyl) TSL 8330,
Anti-fingerprint, the antifouling novel perfluoropolyether alkoxysilane of KH560, HDI trimer reaction synthesizing new, and it is applied to the substrates such as glass
Surface provides excellent soil resistance and wearability.
In order to solve the above-mentioned technical problem, the present invention adopts the following technical scheme:
A kind of novel perfluoropolyether alkoxysilane compound, it is characterised in that shown in its structural formula such as formula (1):
Wherein:PFPE molecular weight MW is 2500-5000.
A kind of synthetic method of novel perfluoropolyether alkoxysilane compound, it is characterised in that include the following steps:
(a) it is added in reaction vessel after diluting HDI trimer with solvent, is uniformly mixed again with solvent dilution under stirring
Terminal hydroxy group perfluoropolyether, 3- (2- amino-ethyl) TSL 8330 mixture are gradually dropped, after completion of dropwise addition in
It is stirred insulation reaction 6 hours under reaction temperature；
(b) 3- (2,3- epoxy identical with 3- (2- amino-ethyl) TSL 8330 molal quantity is added dropwise again
Third oxygen) propyl trimethoxy silicane (KH560), up to perfluoropolyether alkoxyl silicone after the reaction was continued under reaction temperature 6 hours
Hydride compounds.
Further, synthetic route are as follows:
Step (a):
Step (b):
Further, terminal hydroxy group perfluoropolyether, 3- (2- amino-ethyl) TSL 8330, KH560, HDI tri-
It is 1:2:2:1 that aggressiveness, which reacts molar ratio,.
Further, terminal hydroxy group perfluoropolyether molecular weight MW is 2500-5000.
Further, solvent is fluorine ether solvents.
Further, step (a) and step (b) reaction temperature are 25-40 DEG C.
The present invention is by adopting the above-described technical solution, have the advantages that
1, novel perfluoropolyether alkoxysilane compound of the invention shows excellent soil resistance, fingerprint resistance and wear-resisting
Property, it is applied to the crosslinked solidifications of substrate surfaces such as glass, plastics, film, forms one layer of firm film, imparting substrate is excellent is resisted
Fingerprint soil resistance and wearability solve the problems, such as wearability deficiency.
2, novel perfluoropolyether alkoxysilane compound synthesis method of the invention passes through terminal hydroxy group perfluoropolyether, 3- (2- ammonia
Base ethyl) TSL 8330, KH560, HDI trimer reaction synthesizing new anti-fingerprint, antifouling perfluoropolyether
Alkoxy silane, and be applied to the substrate surfaces such as glass formation film and excellent anti-fingerprint anti-pollution and wearability are provided.
Specific embodiment
A kind of novel perfluoropolyether alkoxysilane compound of the invention, shown in structural formula such as formula (1):
Wherein:PFPE molecular weight MW is 2500-5000.
A kind of synthetic method of novel perfluoropolyether alkoxysilane compound, includes the following steps:
(a) it is added in reaction vessel after diluting HDI trimer with solvent, is uniformly mixed again with solvent dilution under stirring
Terminal hydroxy group perfluoropolyether, 3- (2- amino-ethyl) TSL 8330 mixture are gradually dropped, after completion of dropwise addition in
It is stirred insulation reaction 6 hours under reaction temperature.
(b) 3- (2,3- epoxy identical with 3- (2- amino-ethyl) TSL 8330 molal quantity is added dropwise again
Third oxygen) propyl trimethoxy silicane (KH560), up to perfluoropolyether alkoxyl silicone after the reaction was continued under reaction temperature 6 hours
Hydride compounds.
Terminal hydroxy group perfluoropolyether, 3- (2- amino-ethyl) TSL 8330, KH560, HDI trimer reaction
Molar ratio is 1:2:2:1, and terminal hydroxy group perfluoropolyether molecular weight MW is 2500-5000.Solvent is fluorine ether solvents, step (a) and step
Suddenly (b) reaction temperature is 25-40 DEG C.Synthetic route are as follows:
Step (a):
Step (b):
Synthesis example 1:
It is molten that fluorine ether is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Agent 25ml and the dissolution of HDI trimer 2.52g (5mmol) agitation and dilution, then the terminal hydroxy group perfluor that will be uniformly mixed with fluorine ether solvents
Polyethers 12.5g (5mmol, molecular weight MW=2500), 3- (2- amino-ethyl) TSL 8330 2.22g
(10mmol) mixture is gradually dropped, 30 DEG C stirring insulation reaction 6 hours after completion of dropwise addition, then KH560 2.36g is added dropwise
(10mmol) drips 30 DEG C of stirring insulation reactions decompression in 6 hours removal solvent up to product, products therefrom structural formula are as follows:
Wherein PFPE molecular weight MW=2500.
Synthesis example 2:
It is molten that fluorine ether is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Agent 25ml and the dissolution of HDI trimer 2.52g (5mmol) agitation and dilution, then the terminal hydroxy group perfluor that will be uniformly mixed with fluorine ether solvents
Polyethers 15g (5mmol, molecular weight MW=3000), 3- (2- amino-ethyl) TSL 8330 2.22g (10mmol)
Mixture is gradually dropped, 30 DEG C stirring insulation reaction 6 hours after completion of dropwise addition, then KH560 2.36g (10mmol) is added dropwise, and is added dropwise
The decompression in 6 hours of complete 30 DEG C of stirrings insulation reaction removes solvent up to product, products therefrom structural formula are as follows:
Wherein PFPE molecular weight MW=3000.
Synthesis example 3:
It is molten that fluorine ether is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Agent 25ml and the dissolution of HDI trimer 2.52g (5mmol) agitation and dilution, then the terminal hydroxy group perfluor that will be uniformly mixed with fluorine ether solvents
Polyethers 20g (5mmol, molecular weight MW=4000), 3- (2- amino-ethyl) TSL 8330 2.22g (10mmol)
Mixture is gradually dropped, 30 DEG C stirring insulation reaction 6 hours after completion of dropwise addition, then KH560 2.36g (10mmol) is added dropwise, and is added dropwise
The decompression in 6 hours of complete 30 DEG C of stirrings insulation reaction removes solvent up to product, products therefrom structural formula are as follows:
Wherein PFPE molecular weight MW=4000.
Synthesis example 4:
It is molten that fluorine ether is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Agent 25ml and the dissolution of HDI trimer 2.52g (5mmol) agitation and dilution, then the terminal hydroxy group perfluor that will be uniformly mixed with fluorine ether solvents
Polyethers 25g (5mmol, molecular weight MW=5000), 3- (2- amino-ethyl) TSL 8330 2.22g (10mmol)
Mixture is gradually dropped, 30 DEG C stirring insulation reaction 6 hours after completion of dropwise addition, then KH560 2.36g (10mmol) is added dropwise, and is added dropwise
The decompression in 6 hours of complete 30 DEG C of stirrings insulation reaction removes solvent up to product, products therefrom structural formula are as follows:
Wherein PFPE molecular weight MW=5000.
Comparative example 1:
It is molten that fluorine ether is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Agent 25ml and the dissolution of HDI trimer 2.52g (5mmol) agitation and dilution, then the terminal hydroxy group perfluor that will be uniformly mixed with fluorine ether solvents
Polyethers 7g (5mmol, molecular weight MW=1400), 3- (2- amino-ethyl) TSL 8330 2.22g (10mmol)
Mixture is gradually dropped, 30 DEG C stirring insulation reaction 6 hours after completion of dropwise addition, then KH560 2.36g (10mmol) is added dropwise, and is added dropwise
The decompression in 6 hours of complete 30 DEG C of stirrings insulation reaction removes solvent up to product, products therefrom structural formula are as follows:
Wherein PFPE molecular weight MW=1400.
Comparative example 2:
3- isocyanide is added in the 150ml three-necked flask equipped with constant temperature blender with magnetic force, constant pressure funnel and thermometer
Perester radical propyl trimethoxy silicane and organotin catalysts, be stirred at room temperature it is lower be added dropwise equivalent with fluorine ether solvents be uniformly mixed
Terminal hydroxy group perfluoropolyether, room temperature is stirred to react 5h after completion of dropwise addition, and decompression removal solvent is up to product, products therefrom structural formula
Are as follows:
Wherein PFPE molecular weight MW=5000.
Comparative example 3: the mobile phone glass screen without any processing is used.
Test example 1: the measurement of contact angle
The novel perfluoropolyether alkoxysilane compound that the present invention synthesizes is configured to the spray of anti-fingerprint agent (concentration 0.1%) solution
It is applied on mobile phone glass screen, forms the film of fluorine-silicon copolymer object after crosslinked room temperature curing 0.5h, then use contact angle instrument
Film is tested to the contact angle of water and atoleine.25 DEG C of each sample testings of environment temperature three times, take its average value.Contact angle
Bigger, surface can be smaller.
Test example 2: the evaluation and test to ink soil resistance
Oil pen's test: drawing a line with oil pen on mobile phone glass screen film, then examines ink traces change
Change, and is evaluated with following standard
E: ink rapid desufflation
F: ink portions are shunk
NG: ink is not shunk substantially
Test example 3: the evaluation and test of anti-finger printing
Colored dyes are stamped on finger, and finger is forced into holding 5 seconds on mobile phone glass screen film with 1 kilogram, so
It is wiped with non-dust cloth fingerprint 5 times, and is evaluated with following standard back and forth afterwards
E: stain is not left
F: there are a small number of stains
NG: there are most stains
Test example 4: the evaluation and test of wearability
It is tested using wear resistant instrument, with steel wool (BONSTAR#0000,12mm diameter) on mobile phone glass screen film
To load 1kg, the horizontal friction treatment of wiping speed 1800mm/min carries out friction treatment 2000 times back and forth respectively and 8000 times past
It is multiple.Commentary survey contact angle, soil resistance and anti-finger printing as above after friction treatment.
1 test result of table
From table 1 it follows that novel the anti-fingerprint of the invention, (synthesis of antifouling novel perfluoropolyether alkoxysilane compound
Example 1 to 4) excellent soil resistance, fingerprint resistance and wearability are shown compared with (comparative example 3) when being not handled by；Work as PEPE
When molecular weight too small (comparative example 1) or alkoxy number very little (comparative example 2), wearability weakens significantly, excessively poor.
It is crosslinked that novel perfluoropolyether alkoxysilane compound of the invention is applied to the substrate surfaces such as glass, plastics, film
Solidification forms one layer of firm film, assigns substrate excellent anti-fingerprint soil resistance and wearability, solves that wearability is insufficient to ask
Topic.
The above is only specific embodiments of the present invention, but technical characteristic of the invention is not limited thereto.It is any with this hair
Based on bright, to solve essentially identical technical problem, essentially identical technical effect is realized, made simple change, etc.
With replacement or modification etc., all it is covered by among protection scope of the present invention.
Claims (6)
1. a kind of novel perfluoropolyether alkoxysilane compound, it is characterised in that shown in its structural formula such as formula (1):
Wherein:PFPE molecular weight MW is 2500-5000.
2. a kind of synthetic method of novel perfluoropolyether alkoxysilane compound as described in claim 1, it is characterised in that including
Following steps:
(a) it is added in reaction vessel after diluting HDI trimer with solvent, end hydroxyl uniformly mixed with solvent dilution again under stirring
Base perfluoropolyether, 3- (2- amino-ethyl) TSL 8330 mixture are gradually dropped, in reaction after completion of dropwise addition
At a temperature of stir insulation reaction 6 hours；
(b) 3- (the third oxygen of 2,3- epoxy) identical with 3- (2- amino-ethyl) TSL 8330 molal quantity is added dropwise again
Propyl trimethoxy silicane (KH560), up to novel perfluoropolyether alkoxysilane chemical combination after the reaction was continued under reaction temperature 6 hours
Object.
3. a kind of synthetic method of novel perfluoropolyether alkoxysilane compound according to claim 2, it is characterised in that close
At route are as follows:
Step (a):
Step (b):
4. a kind of synthetic method of novel perfluoropolyether alkoxysilane compound according to claim 2, it is characterised in that: institute
State terminal hydroxy group perfluoropolyether, the 3- (2- amino-ethyl) TSL 8330, the KH560, the HDI trimerization
Precursor reactant molar ratio is 1:2:2:1.
5. a kind of synthetic method of novel perfluoropolyether alkoxysilane compound according to claim 2, it is characterised in that: institute
Stating solvent is fluorine ether solvents.
6. a kind of synthetic method of novel perfluoropolyether alkoxysilane compound according to claim 2, it is characterised in that: step
Suddenly (a) and step (b) reaction temperature are 25-40 DEG C.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201610459015.3A CN106432686B (en) | 2016-06-21 | 2016-06-21 | A kind of novel perfluoropolyether alkoxysilane compound and its synthetic method |
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| US12049537B2 (en) | 2020-04-13 | 2024-07-30 | Akzo Nobel Coatings International B.V. | Fluorinated, alkoxysilyl-functional polymer for anti-stain and anti-scratch coatings |
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