CN108341917A - A kind of hydrophobic auxiliary agent of polyurethane and its preparation and application - Google Patents
A kind of hydrophobic auxiliary agent of polyurethane and its preparation and application Download PDFInfo
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- CN108341917A CN108341917A CN201810140189.2A CN201810140189A CN108341917A CN 108341917 A CN108341917 A CN 108341917A CN 201810140189 A CN201810140189 A CN 201810140189A CN 108341917 A CN108341917 A CN 108341917A
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- polyurethane
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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
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
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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
- C08G18/2805—Compounds having only one group containing active hydrogen
- C08G18/288—Compounds containing at least one heteroatom other than oxygen or nitrogen
- C08G18/2885—Compounds containing at least one heteroatom other than oxygen or nitrogen containing halogen 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
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3203—Polyhydroxy compounds
- C08G18/3206—Polyhydroxy compounds aliphatic
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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
- C14—SKINS; HIDES; PELTS; LEATHER
- C14C—CHEMICAL TREATMENT OF HIDES, SKINS OR LEATHER, e.g. TANNING, IMPREGNATING, FINISHING; APPARATUS THEREFOR; COMPOSITIONS FOR TANNING
- C14C11/00—Surface finishing of leather
- C14C11/003—Surface finishing of leather using macromolecular compounds
- C14C11/006—Surface finishing of leather using macromolecular compounds using polymeric products of isocyanates (or isothiocyanates) with compounds having active hydrogen
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- Chemical Kinetics & Catalysis (AREA)
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- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Treatment And Processing Of Natural Fur Or Leather (AREA)
Abstract
The invention discloses a kind of preparation methods of the hydrophobic auxiliary agent of polyurethane for leather finishing agent field, it is using toluene di-isocyanate(TDI) (TDI) or methyl diphenylene diisocyanate (MDI), neopentyl glycol, butanediol or pentaerythrite as raw material, add perfluoroalkyl ethanol, isopropanol terminates reaction, condensation reaction is carried out under condition of heating and stirring, the hydrophobic auxiliary agent of polyurethane of final obtained function admirable.Product made from this law is light yellow transparent liquid, and hydrophobic effect is good, takes and is added in leather polyurethane finishing agent on a small quantity, and the addition quality of auxiliary agent and the ratio of finishing agent quality are 0.5~5:100, you can significantly improve the surface hydrophobic performance of leather surface coating agent coating, while the physical property such as feel and gloss for not influencing film itself.Present invention process process is simple, and reaction conversion ratio is high, and without post-processing, product is easy to get environmental protection, and reaction condition is mildly convenient for control, and raw material cost is low, is very beneficial for large-scale production.
Description
Technical field
The invention belongs to hydrophobing agent preparation field, it is related specifically to a kind of polyurethane hydrophobing agent and its preparation and user
Method.
Background technology
Wettability of the surface has vital effect to material application, and low-surface energy substance is to material surface modification pair
Improving material surface hydrophobicity has vital effect.Fluorochemical urethane by its excellent thermal stability, chemical inertness,
Low-surface-energy, biocompatibility become the focus on research direction of domestic and international hydrophobing agent.In fields such as footwear material, luggage and clothes,
Largely use leather substance, such as corium, PU artificial leathers and PVC artificial leather；In order to make these leather substances have special decorative pattern
And feel, moditied processing usually is carried out to leather Base with polyurethane finishing agent.The modified coatings of this polyurethane system, due to
The waterproof and antigraffiti properties on surface are insufficient, receive and denounce.Ready-made hydrophobic polyurethane resin is directly used, is on the one hand led
It causes the coating finally obtained there is no special feel and decorative pattern, loses the function of covering with paint；On the other hand, and there are fluorine-containing to dredge
Water-resin, it is expensive, it is unable to get promotion and application.Therefore the hydrophobic auxiliary agent of the fluorochemical urethane haveing excellent performance is developed, it is small
Be added in finishing agent to ratio, so as to get leather surface modified coatings keep original decorative pattern and feel, while again can
Hydrophobic performance is obtained, the upgrading to leather substance has great meaning.
Since fluorine-containing cost of material is high so that the production cost of fluorochemical urethane is higher.Therefore, the hydrophobic auxiliary agent of polyurethane
Research in, most important is exactly that hydrophobic synthetic effect is good, the controllable fluorochemical urethane of cost, i.e. the fewer fluorine dosage the better.Mesh
Before, the domestic hydrophobic Auxiliaries Industry application of polyurethane is still less, relies primarily in external import.Therefore develop synthesis cost it is low,
The high performance hydrophobic auxiliary agent of polyurethane has wide market, has very high Development volue.
Chinese patent CN103992043A disclose it is a kind of with chain fluoroalkyl by being made in hydrolysis extraction to perfluoro solvent
The method for obtaining hydrophobing agent, but using a large amount of fluoropolymer and expensive perfluoro solvent is used in the method, the preparation
Method is of high cost, significantly limits its practical application.
In conclusion after traditional polyurethane finishing agent covers with paint, lacquer, colour wash, etc. leather base, special feel, decorative pattern and light are formd
Pool, there is also the weak deficiencies of the waterproof on finishing agent surface and antigraffiti properties.Directly use ready-made hydrophobic polyurethane tree
Fat, function that is expensive, and not covering with paint, lacquer, colour wash, etc..Therefore a kind of synthesis technology of offer is simple, production process cost is controllable and raw
The preparation method that production raw material is easy to get is to prepare the hydrophobic auxiliary agent of polyurethane of chemical inertness, good biocompatibility and low surface energy
It is crucial.
Invention content
The present invention provides a kind of preparation methods of the hydrophobic auxiliary agent of polyurethane.Polyurethane that this method is prepared is hydrophobic to be helped
Agent is yellow or pale yellow transparent thick liquid, and synthesis cost is low, chemical inertness, good biocompatibility and low surface energy, can
For use as improvement surface hydrophobic material.
The present invention is achieved through the following technical solutions：
A kind of preparation method of the hydrophobic auxiliary agent of polyurethane, which is characterized in that comprise the steps of：
(1) it in the case where completely cutting off air conditions, takes diisocyanate to be dissolved in dimethylformamide, obtains solution A, take polyalcohol
It is dissolved in dimethylformamide, obtains solution B, solution B is added drop-wise in solution A, is reacted under condition of heating and stirring, end is made
Isocyanate group performed polymer；
(2) it takes perfluoro octyl ethanol to be dissolved in dimethylformamide, obtains solution C, solution C is added to isocyanate terminated
In base performed polymer, it is eventually adding isopropanol or n-butanol terminates reaction, react under condition of heating and stirring, be down to after reaction
Room temperature obtains the hydrophobic auxiliary agent of polyurethane.
Preferably, the molar ratio of diisocyanate and polyalcohol described in step (1) is 1.2:1~3.4:1；Diisocyanate
The mass ratio of ester and dimethylformamide is 1:1~1:2；The mass ratio of polyalcohol and dimethylformamide is 1:2~1:3.
Preferably, the condition of step (1) described reaction is：20~50 DEG C of temperature, 250~450rpm of mixing speed, reaction
2~4h of time.
Preferably, in step (2), solution C is added to the drop speed of 1~2ml/min in terminal isocyanate group performed polymer.
Preferably, the condition of step (2) described reaction is：Temperature be 50~80 DEG C, 250~450rpm of mixing speed, instead
4~7 hours between seasonable.
Preferably, the perfluoro octyl ethanol described in step (2) accounts for 5~25wt% of system gross weight.
Preferably, the diisocyanate described in step (1) is toluene di-isocyanate(TDI) and methyl diphenylene diisocyanate
One or both of.
Preferably, the polyalcohol described in step (1) be one or both of neopentyl glycol, butanediol and pentaerythrite with
On.
The hydrophobic auxiliary agent of polyurethane prepared by the method.
The application of the hydrophobic auxiliary agent of polyurethane, for being surface modified to leather, specific method is the hydrophobic auxiliary agent：
The hydrophobic auxiliary agent of polyurethane is sufficiently mixed with polyurethane finishing agent, the addition quality of auxiliary agent and the ratio of finishing agent quality are 0.5
~5:100, then film is carried out on leather Base, in an oven under the conditions of 120 DEG C, baking 5min drying, after being covered with paint, lacquer, colour wash, etc.
Leather.
Specific implementation mode
Below in conjunction with specific embodiment, the invention will be further described, but scope of the present invention is not
It is confined to the involved range of embodiment.
Embodiment 1
(1) 13.92g toluene di-isocyanate(TDI)s, 20g dimethylformamides is taken to be added to heating, magnetic agitation and temperature
It spends in the 100ml three-necked flasks of controller, sealing dissolving then takes 5.07g neopentyl glycols to be dissolved in 10.14g dimethyl formyls
Amine is simultaneously added dropwise to flask by constant pressure funnel, and drop speed is 1ml/min, after being added dropwise, in 40 DEG C, mixing speed 300rpm
Under the conditions of react 2h, above reaction process need to completely cut off air.
(2) it takes 5g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides and is added in step (1) reaction system,
System is then warming up to 60 DEG C, under the conditions of maintaining the temperature at 60 DEG C, mixing speed 400rpm, reacts 4h, after add it is a small amount of different
Propyl alcohol terminates reaction, measures the concentration of system isocyanate base, until a concentration of the 0 of system isocyano, stops stirring, terminates
Reaction, temperature discharge after being reduced to room temperature, illustrate in polyurethane system at this time, and the reaction was complete for isocyanate groups, reaction
Conversion ratio is up to 100%.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 0.5：100, mixing
After stir evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 93 °.
Embodiment 2
(1) 13.92g toluene di-isocyanate(TDI)s, 20g dimethylformamides is taken to be added to heating, magnetic agitation and temperature
It spends in the 100ml three-necked flasks of controller, sealing dissolving then takes 4.39g butanediols to be dissolved in 10g dimethylformamides, and
It is added dropwise to flask by constant pressure funnel, drop speed is that drop speed is 2ml/min, and 3h, reaction temperature 35 are reacted after being added dropwise
DEG C, mixing speed 400rpm, the above reaction process need to completely cut off air.
(2) it takes 10g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides to be added at one time in flask, then will
System is warming up to 60 DEG C, maintains the temperature under the conditions of 60 DEG C, mixing speed 300rpm, reacts 7h, finally adds a small amount of n-butanol
It terminates and reacts, the concentration of isocyanate group in measurement system stops stirring until a concentration of the 0 of system isocyano, terminates anti-
It answers, temperature discharges after being reduced to room temperature.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 3：100, after mixing
It stirs evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 98 °.
Embodiment 3
(1) 13.92g toluene di-isocyanate(TDI)s, 20g dimethylformamides is taken to be added to heating, magnetic agitation and temperature
It spends in the 100ml three-necked flasks of controller, sealing dissolving then takes 2.54g neopentyl glycols and 2.20g butanediols to be dissolved in 10g
Dimethylformamide, and flask is added dropwise to by constant pressure funnel, drop speed is that drop speed is 1.5ml/min, anti-after being added dropwise
It is 50 DEG C to answer 2h, reaction temperature, and mixing speed 350rpm, the above reaction process need to completely cut off air.
(2) it takes 10g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides to be added at one time in flask, then will
System is warming up to 60 DEG C, maintains the temperature under the conditions of 60 DEG C, mixing speed 250rpm, reacts 5h, finally adds a small amount of isopropanol
It terminates and reacts, the concentration of isocyanate group in measurement system stops stirring until a concentration of the 0 of system isocyano, terminates anti-
It answers, temperature discharges after being reduced to room temperature.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 3.5：100, mixing
After stir evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 103 °.
Embodiment 4
(1) it takes 17.4g methyl diphenylene diisocyanates, 35.8g dimethylformamides to be added to stir with heating, magnetic force
Mix and the 150ml three-necked flasks of temperature controller in, sealing dissolving then takes 2.17g neopentyl glycols and 1.88g butanediols to dissolve
It is added dropwise to flask in 10g dimethylformamides, and by constant pressure funnel, drop speed is that drop speed is 1ml/min, after being added dropwise
2.5h is reacted, reaction temperature is 45 DEG C, and mixing speed 350rpm, the above reaction process need to completely cut off air.
(2) it takes 6g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides to be added at one time in flask, then by body
System is warming up to 60 DEG C, mixing speed 350rpm under the conditions of 60 DEG C, reacts 7h, finally adds a small amount of isopropanol and terminates reaction, surveys
The concentration for determining isocyanate group in system stops stirring until a concentration of the 0 of system isocyano, and reaction was completed, and temperature reduces
It discharges after to room temperature.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 1.5：100, mixing
After stir evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 92 °.
Embodiment 5
(1) it takes 17.4g methyl diphenylene diisocyanates, 35.8g dimethylformamides to be added to stir with heating, magnetic force
Mix and the 150ml three-necked flasks of temperature controller in, sealing dissolving, then take 3.75g butanediols to be dissolved in 10g dimethyl formyls
Amine, and flask is added dropwise to by constant pressure funnel, drop speed is that drop speed is 2ml/min, and 4h is reacted after being added dropwise, keeps reaction
Temperature is 25 DEG C, and mixing speed 250rpm, the above reaction process need to completely cut off air.
(2) it takes 12g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides to be added at one time in flask, then will
System is warming up to 60 DEG C, mixing speed 400rpm under the conditions of 60 DEG C, reacts 4h, finally adds a small amount of n-butanol and terminates reaction,
The concentration of isocyanate group in measurement system, until a concentration of the 0 of system isocyano.Stop stirring, reaction was completed, temperature drop
As low as discharging after room temperature.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 3：100, after mixing
It stirs evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 96 °.
Embodiment 6
(1) it takes 17.4g methyl diphenylene diisocyanates, 35.8g dimethylformamides to be added to stir with heating, magnetic force
Mix and the 150ml three-necked flasks of temperature controller in, sealing dissolving then takes 2.17g neopentyl glycols and 1.88g butanediols to dissolve
10g dimethylformamides, and flask is added dropwise to by constant pressure funnel, drop speed is that drop speed is 1.5ml/min, after being added dropwise
4h is reacted, reaction temperature is 30 DEG C, and mixing speed 450rpm, the above reaction process need to completely cut off air.
(2) it takes 10g perfluoro octyl ethanols to be dissolved in 15g dimethylformamides to be added at one time in flask, then will
System is warming up to 80 DEG C, maintains the temperature under the conditions of 80 DEG C, mixing speed 450rpm, reacts 5h, finally adds a small amount of isopropanol
It terminates and reacts, the concentration of isocyanate group in measurement system stops stirring until a concentration of the 0 of system isocyano, terminates anti-
It answers, temperature discharges after being reduced to room temperature.
(3) hydrophobing agent being prepared is added in polyurethane finishing agent, the mass ratio of addition is 5:100, after mixing
It stirs evenly.Mixed material carries out film with coated rod on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..The face coat of artificial leather can must be made to have hydrophobic performance.Through measuring artificial leather surface
The contact angle of coating and water is 108 °.
Claims (10)
1. a kind of preparation method of the hydrophobic auxiliary agent of polyurethane, which is characterized in that comprise the steps of：
(1) it in the case where completely cutting off air conditions, takes diisocyanate to be dissolved in dimethylformamide, obtains solution A, polyalcohol is taken to dissolve
In dimethylformamide, solution B is obtained, solution B is added drop-wise in solution A, is reacted under condition of heating and stirring, end isocyanide is made
Perester radical performed polymer；
(2) it takes perfluoro octyl ethanol to be dissolved in dimethylformamide, obtains solution C, it is pre- that solution C is added to terminal isocyanate group
In aggressiveness, it is eventually adding isopropanol or n-butanol terminates reaction, reacted under condition of heating and stirring, be down to room temperature after reaction
Obtain the hydrophobic auxiliary agent of polyurethane.
2. preparation method according to claim 1, which is characterized in that diisocyanate and polyalcohol described in step (1)
Molar ratio be 1.2:1~3.4:1；The mass ratio of diisocyanate and dimethylformamide is 1:1~1:2；Polyalcohol and two
The mass ratio of methylformamide is 1:2~1:3.
3. preparation method according to claim 2, which is characterized in that the condition of step (1) described reaction is：Temperature 20~
50 DEG C, 250~450rpm of mixing speed, 2~4h of reaction time.
4. according to claims 1 to 3 any one of them preparation method, which is characterized in that in step (2), solution C with 1~
The drop speed of 2ml/min is added in terminal isocyanate group performed polymer.
5. preparation method according to claim 4, which is characterized in that the condition of step (2) described reaction is：Temperature is 50
~80 DEG C, 250~450rpm of mixing speed, 4~7 hours reaction time.
6. according to claims 1 to 3 any one of them preparation method, which is characterized in that the perfluoro capryl second described in step (2)
Alcohol accounts for 5~25wt% of system gross weight.
7. according to claims 1 to 3 any one of them preparation method, which is characterized in that the diisocyanate described in step (1)
For one or both of toluene di-isocyanate(TDI) and methyl diphenylene diisocyanate.
8. according to claims 1 to 3 any one of them preparation method, which is characterized in that the polyalcohol described in step (1) is new
One or more of pentanediol, butanediol and pentaerythrite.
9. the hydrophobic auxiliary agent of polyurethane prepared by any one of claim 1~8 the method.
10. the application of the hydrophobic auxiliary agent of polyurethane described in claim 9, which is characterized in that the hydrophobic auxiliary agent is used to carry out leather
Surface modification, specific method are：The hydrophobic auxiliary agent of polyurethane is sufficiently mixed with polyurethane finishing agent, addition quality and the painting of auxiliary agent
The ratio for adoring agent quality is 0.5~5:100, then film is carried out on leather Base, in an oven under the conditions of 120 DEG C, baking
5min is dried, the leather after being covered with paint, lacquer, colour wash, etc..
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| CN201810140189.2A CN108341917A (en) | 2018-02-11 | 2018-02-11 | A kind of hydrophobic auxiliary agent of polyurethane and its preparation and application |
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| CN201810140189.2A CN108341917A (en) | 2018-02-11 | 2018-02-11 | A kind of hydrophobic auxiliary agent of polyurethane and its preparation and application |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574822A (en) * | 2020-06-04 | 2020-08-25 | 北京浦江兄弟科技有限公司 | Polyurethane hydrophobic film, preparation method and application thereof |
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| US20100324253A1 (en) * | 2008-02-12 | 2010-12-23 | Fujifilm Corporation | Fluorine-containing polyfunctional silicon compound and method for producing fluorine-containing polyfunctional silicon compound |
| CN101979756A (en) * | 2010-09-20 | 2011-02-23 | 上海汇得化工有限公司 | Drying agent for polyurethane synthetic leather and preparation method thereof |
| CN105113258A (en) * | 2015-08-14 | 2015-12-02 | 湖州市云巢染料化工厂 | Water-based fluorine-containing water-repellent and oil-repellent agent prepared from 2,2-dimethylolbutyric acid |
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2018
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN1661158A (en) * | 2004-02-24 | 2005-08-31 | 福盈科技化学股份有限公司 | Hydrophobic and oleophobic agent in fluoric solvent type and producing method |
| US20100324253A1 (en) * | 2008-02-12 | 2010-12-23 | Fujifilm Corporation | Fluorine-containing polyfunctional silicon compound and method for producing fluorine-containing polyfunctional silicon compound |
| CN101979756A (en) * | 2010-09-20 | 2011-02-23 | 上海汇得化工有限公司 | Drying agent for polyurethane synthetic leather and preparation method thereof |
| CN105113258A (en) * | 2015-08-14 | 2015-12-02 | 湖州市云巢染料化工厂 | Water-based fluorine-containing water-repellent and oil-repellent agent prepared from 2,2-dimethylolbutyric acid |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111574822A (en) * | 2020-06-04 | 2020-08-25 | 北京浦江兄弟科技有限公司 | Polyurethane hydrophobic film, preparation method and application thereof |
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Application publication date: 20180731 |