CN106752857A - A kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate - Google Patents

A kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate Download PDF

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CN106752857A
CN106752857A CN201611064823.6A CN201611064823A CN106752857A CN 106752857 A CN106752857 A CN 106752857A CN 201611064823 A CN201611064823 A CN 201611064823A CN 106752857 A CN106752857 A CN 106752857A
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preparation
acrylate
film
drop
paamh
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姚伯龙
赵海平
郑春森
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Jiangnan University
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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
    • C09D175/14—Polyurethanes having carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
    • C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
    • C08F220/04—Acids; Metal salts or ammonium salts thereof
    • C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
    • 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
    • C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
    • C08G18/6295—Polymers of silicium containing compounds having carbon-to-carbon double bonds
    • 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
    • C08G18/67—Unsaturated compounds having active hydrogen
    • C08G18/671—Unsaturated compounds having only one group containing active hydrogen
    • C08G18/672—Esters of acrylic or alkyl acrylic acid having only one group containing active hydrogen
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/75—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic
    • C08G18/751—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring
    • C08G18/752—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group
    • C08G18/753—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group
    • C08G18/755—Polyisocyanates or polyisothiocyanates cyclic cycloaliphatic containing only one cycloaliphatic ring containing at least one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group containing one isocyanate or isothiocyanate group linked to the cycloaliphatic ring by means of an aliphatic group having a primary carbon atom next to the isocyanate or isothiocyanate group and at least one isocyanate or isothiocyanate group linked to a secondary carbon atom of the cycloaliphatic ring, e.g. isophorone diisocyanate
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40—Additives
    • C09D7/60—Additives non-macromolecular
    • C09D7/63—Additives non-macromolecular organic

Abstract

It is an object of the invention to provide a kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate.The present invention introduces silane coupler, hydroxy-ethyl acrylate and sulfonic group acrylamide monomer, then introduce double bond using hydroxyl reaction in half blocked polyurethane and main chain with acrylic ester monomer as primary raw material using radical polymerization.Sulfonic group can assign film good hydrophily wherein on main chain；Silane coupler, while the silicone hydroxyl not being condensed can also further lift the hydrophily of film, can assign film good anti-fog performance with teos hydrolysis cured coating film；The introducing of double bond realizes the photocuring of acrylate.After the resin system film-forming, while excellent adhesive force, water resistance, hardness and high transparency is ensured, also with excellent hydrophily, and can over the transparent substrate have good anti-fog effect.

Description

A kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate
Technical field
The invention belongs to technical field of polymer materials, and in particular to a kind of super hydrophilic antifog painting of dual cure acrylate The preparation method of layer.
Background introduction
Transparent base (such as glass) is indispensable material in our daily lifes and production, but it is in use Easily there is fogging phenomenon, cause light transmittance, the reflectance reduction of material surface, influence sight line, brought to our life all Many inconvenience, or even serious harm can be caused.Anti-fog method main at present mainly has two kinds：Electrothermal way and the antifog method of coating. Compared with electrothermal way, coating it is antifog because its is easy to use, application finishes Non-energy-consumption, simple production process, equipment cost be low, investment It is low and more have wide practical use；And antifogging coating often be generally divided into principle it is super-hydrophobic and super hydrophilic two kinds, using tree Fat realizes that hydrophobic current report is a lot, and Venkateswara etc. has been prepared as raw material using MTMS and connect Feeler is up to 173 ° of super-hydrophobic film, but the also difficult realization of real application, is mainly manifested in poor adhesive force, the low aspect of hardness.It is super It is hydrophilic because the relative sight for being easier to realize and attract more people, Massachusetts Institute of Technology Rubner professors research group takes layer SiO of the shape self-assembling method 7nm2Nano-particle forms contact angle and is less than 5 ° with polyelectrolyte alternating deposit glass surface Super hydrophilic porous membrane.But most inorganic nano-particles are complicated because of preparation process, and coating process difficulty is big, and majority needs sintering etc. Make its applied environment very limited；Later researchers expect preparing antifogging coating using pure resin again, and such as Zoromba is developed A kind of UV cured polyurethane acrylate anti-fog coatings of excellent performance, but most of pure resins accomplish hydrophily and resistance to because being difficult Aqueous balance, prepares super hydrophilic report and has become study hotspot using organic inorganic hybridization.
The design is changed using 3- (trimethoxysilyl) propyl group -2- methyl -2- acrylate (MPS) silane coupler Property acrylic resin be main chain, introduce hydrophilic monomer 2- acrylamide-2-methyl propane sulfonics (AMPS), innovatively employ Tetraethyl orthosilicate (TEOS) makees Novel curing agent, is shunk with the hydroxyl of silane coupler (MPS) hydrolysis and solidified；Simultaneously using half Blocked polyurethane introduces double bond on main chain and realizes photocuring, improves curing rate.The design also utilizes tetraethyl orthosilicate (TEOS) introduce great amount of hydroxy group and the low surface tension using Si-O-Si keys takes hydroxyl to coating surface, the advantage of this design It is hydrophilic simultaneously in guarantee, also assign coating fabulous hardness and water resistance, overcome traditional super hydrophilic antifogging coating and repeat The shortcomings of utilization rate is low, poor water resistance, transparency are low, anti-fog effect is bad.
The content of the invention
It is an object of the invention to provide a kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate.This hair It is bright with acrylic ester monomer as primary raw material, silane coupler, hydroxy-ethyl acrylate and sulfonic acid are introduced using radical polymerization Base acrylamide monomer, then double bond is introduced using hydroxyl reaction in half blocked polyurethane and main chain.Wherein sulfonic group can on main chain Assign film good hydrophily；Silane coupler can be with teos hydrolysis cured coating film, while the silicone hydroxyl not being condensed The hydrophily of film can be also further lifted, assigns film good anti-fog performance；The introducing of double bond realizes acrylate Photocuring.After the resin system film-forming, can while excellent adhesive force, water resistance, hardness and high transparency is ensured, Also there is excellent hydrophily, and there is good anti-fog effect over the transparent substrate.
The technical scheme is that：
A kind of preparation method of heat curing-type polyacrylate hydrophilic antifogging coating, comprises the following steps：
(1) preparation of acrylic resin modified performed polymer：Will metering acrylic acid (AA), 2- acrylamide -2- methyl-prop sulphurs Sour (AMPS), feature acrylic monomers, silane coupler, N, N-dimethylformamide (DMF) are added equipped with agitator, condensation Pipe, drying for nitrogen conduit and constant pressure funnel (carried out post treatment to AA in advance and remove polymerization inhibitor) room temperature in four-hole bottle and stir Mix uniform, be passed through nitrogen protection, be progressively warming up to 80 DEG C；Metering initiator is weighed, is dissolved in a small amount of DMF, leaked with constant pressure addition It is 2 seconds/drop that bucket control drop speed, adds about half initiator, reacts 4h, after remaining part is added to body so that identical drop speed is whole After reacting 3h again in system, PAAMH is counted as, it is standby.
(2) preparation of polyurethane modified acrylic resin：Will metering IPDI (IPDI), acrylic acid hydroxyl Ethyl ester (HEA), acetone (ACE), catalyst are added and to dry there-necked flask equipped with agitator, condenser pipe, nitrogen conduit, and room temperature is stirred Mix uniform, be passed through nitrogen protection, be progressively warming up to 55 DEG C；Metering tetramethoxy phenol (MEHQ) is weighed simultaneously is dissolved in a small amount of acetone (ACE), fast drop reacts 2h in system.Using in di-n-butylamine method titration system dissociate-nco value after, make system cold But to room temperature, product is transferred to constant pressure funnel, and first step product PAAMH is added dropwise to the drop speed of 2 seconds/drop In, add catalyst, dissociate in continuous titration system-NCO content adds a small amount of methyl alcohol after reaching theory, by it is remaining- NCO reactions are complete, and 2270cm is detected with infrared spectrometer-1The characteristic absorption peak for locating-NCO is wholly absent, and finally revolves product Turn a small amount of acetone in evaporimeter removing system, obtain final product the super hydrophilic antifog resin of dual cure, be counted as PAAMH-IH.
(3) preparation of cured film：A certain amount of PAAMH-IH is weighed, the light trigger of polymer quality 3% is added Irgacure1173,0.3% levelling agent 3288, a certain amount of tetraethyl orthosilicate (TEOS), three hydroxyls that account for resin system 25% Propane tri (TMPTA) and ethanol, then adjust sample pH value=13 or so, lucifuge with the ammoniacal liquor that concentration is 25% After being stirred at room temperature uniformly, resin is coated in clean glass slide rapidly.45 DEG C of lucifuges toast 2h, then oven temperature is adjusted into 75 DEG C baking 2h, finally puts it into and solidifies 35~40s in the portable UV curing of 1.5kw.
Feature acrylic monomers described in step (1) is hydroxy-ethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA) at least one in；
Initiator described in step (1) is at least in azodiisobutyronitrile (AIBN), dibenzoyl peroxide (BPO) Kind；
Silane coupler described in step (1) is 3- (trimethoxysilyl) propyl group -2- methyl -2- acrylate (MPS), at least one in γ-methacryloxypropyl trimethoxy silane (KH-570)；
Catalyst described in step (2) is at least one in dibutyl tin laurate, stannous octoate；
The beneficial effects of the invention are as follows：Reacted more than, synthesis obtains water-fast, scratch resistance and stronger mechanical performance Heat-poly- the modified acrylic ester resin of light dual cure.Can be used for the surface of antifog requirement after the resin solidification film forming.
Specific embodiment
Following embodiment is used to the present invention program is more fully described, but the invention is not limited in described by example Scheme.
Embodiment 1
(1) preparation of acrylic resin modified performed polymer：By 10.00g acrylic acid (AA), 3.09g2- acrylamide -2- first Base propane sulfonic acid (AMPS), 6.00g hydroxy-ethyl acrylates (HEA), 2.00g3- (trimethoxysilyl) propyl group -2- methyl -2- Acrylate (MPS), 50mLN, N-dimethylformamide (DMF) are added equipped with agitator, condenser pipe, nitrogen conduit and constant pressure drop Liquid funnel dry four-hole bottle in (post treatment was carried out to AA, HEA in advance and removed polymerization inhibitor) being stirred at room temperature uniform, be passed through nitrogen Protection, is progressively warming up to 80 DEG C；0.30g azodiisobutyronitriles (AIBN) are weighed, is dissolved in a small amount of 5mLDMF, leaked with constant pressure addition It is 2 seconds/drop that bucket control drop speed, adds about half initiator, reacts 4h, after remaining part is added to body so that identical drop speed is whole After reacting 3h again in system, PAAMH is denoted as, it is standby.
(2) preparation of polyurethane modified acrylic resin：By 11.50g IPDIs (IPDI), 6.00g Hydroxy-ethyl acrylate (HEA), 50mL acetone (ACE), 0.01g dibutyl tin laurates (DBTDL) are added equipped with agitator, cold Solidifying pipe, nitrogen conduit dry there-necked flask, are stirred at room temperature uniform, are passed through nitrogen protection, are progressively warming up to 55 DEG C；Weigh simultaneously 0.05g tetramethoxies phenol (MEHQ) are dissolved in 5mL acetone (ACE), in fast drop to system, react 2h.Using di-n-butylamine method Dissociate in titration system-nco value after, system is cooled to room temperature, product is transferred to constant pressure funnel, and with 2 seconds/drop Drop speed be added dropwise in first step product PAAMH, add catalyst 0.06gDBTDL, in continuous titration system dissociate- NCO content adds a small amount of methyl alcohol after reaching theory, and remaining-NCO reactions is complete, and 2270cm is detected with infrared spectrometer-1 The characteristic absorption peak for locating-NCO is wholly absent, and finally by product a small amount of acetone in Rotary Evaporators removing system, obtains final product dual Solidify super hydrophilic antifog resin, be denoted as PAAMH-IH.
(3) preparation of cured film：The PAAMH-IH of 1.00g is weighed, adds 0.05g (the 5% of polymer quality) light-initiated Agent Irgacure1173,0.01g levelling agent 3288,0.20g tetraethyl orthosilicates (TEOS), 0.02g trimethylolpropane tris propylene Acid esters (TMPTA) and 30mL ethanol, then adjust sample pH value=13 or so with the ammoniacal liquor that concentration is 25%, and lucifuge is stirred at room temperature After even, resin is coated in clean glass slide rapidly.45 DEG C of lucifuges toast 2h, then oven temperature is adjusted into 75 DEG C of baking 2h, Finally put it into 35~40s of solidification in the portable UV curing of 1.5kw.

Claims (1)

1. a kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate, its characterization step is：
(1) preparation of acrylic resin modified performed polymer：Will metering acrylic acid (AA), 2- acrylamide-2-methyl propane sulfonics (AMPS), feature acrylic monomers, silane coupler, N, N-dimethylformamide (DMF) add equipped with agitator, condenser pipe, Drying for nitrogen conduit and constant pressure funnel (carried out post treatment to AA in advance and remove polymerization inhibitor) to be stirred at room temperature in four-hole bottle Uniformly, nitrogen protection is passed through, 80 DEG C are progressively warming up to；Metering initiator is weighed, is dissolved in a small amount of DMF, use constant pressure funnel It is 2 seconds/drop to control drop speed, adds about half initiator, reacts 4h, after remaining part is all added to system with identical drop speed In react 3h again after, be counted as PAAMH, it is standby；
(2) preparation of polyurethane modified acrylic resin：Will metering IPDI (IPDI), hydroxy-ethyl acrylate (HEA), acetone (ACE), catalyst are added and dry there-necked flask equipped with agitator, condenser pipe, nitrogen conduit, are stirred at room temperature It is even, nitrogen protection is passed through, progressively it is warming up to 55 DEG C；Metering tetramethoxy phenol (MEHQ) is weighed simultaneously is dissolved in a small amount of acetone (ACE), Fast drop reacts 2h in system；Using in di-n-butylamine method titration system dissociate-nco value after, system is cooled to room Temperature, constant pressure funnel is transferred to by product, and is added dropwise in first step product PAAMH with the drop speed of 2 seconds/drop, is added Catalyst, dissociate in continuous titration system-NCO content adds a small amount of methyl alcohol after reaching theory, by remaining-NCO reactions Completely, 2270cm is detected with infrared spectrometer-1The characteristic absorption peak for locating-NCO is wholly absent, finally by product Rotary Evaporators A small amount of acetone in removing system, obtains final product the super hydrophilic antifog resin of dual cure, is counted as PAAMH-IH；
(3) preparation of cured film：A certain amount of PAAMH-IH is weighed, the light trigger of polymer quality 3% is added Irgacure1173,0.3% levelling agent 3288, a certain amount of tetraethyl orthosilicate (TEOS), three hydroxyls that account for resin system 25% Propane tri (TMPTA) and ethanol, then adjust sample pH value=13 or so, lucifuge with the ammoniacal liquor that concentration is 25% After being stirred at room temperature uniformly, resin is coated in clean glass slide rapidly；45 DEG C of lucifuges toast 2h, then oven temperature is adjusted into 75 DEG C baking 2h, finally puts it into and solidifies 35~40s in the portable UV curing of 1.5kw；
Feature acrylic monomers described in step (1) is in hydroxy-ethyl acrylate (HEA), hydroxyethyl methacrylate (HEMA) At least one；
Initiator described in step (1) is at least one in azodiisobutyronitrile (AIBN), dibenzoyl peroxide (BPO)；
Silane coupler described in step (1) be 3- (trimethoxysilyl) propyl group -2- methyl -2- acrylate (MPS), At least one in γ-methacryloxypropyl trimethoxy silane (KH-570)；
Catalyst described in step (2) is at least one in dibutyl tin laurate, stannous octoate.
CN201611064823.6A 2016-11-28 2016-11-28 A kind of preparation method of the super hydrophilic antifogging coating of dual cure acrylate Pending CN106752857A (en)

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Cited By (11)

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CN109868025A (en) * 2019-02-27 2019-06-11 江西省龙海化工有限公司 A kind of preparation method of the super hydrophilic anti-fog coating of waterborne normal-temperature self-crosslinking
CN110903459A (en) * 2019-11-25 2020-03-24 重庆沥智路桥工程有限公司 Hydroxyl-terminated polyurethane methacrylic resin, preparation method and application thereof
CN111057210A (en) * 2019-12-31 2020-04-24 阜阳欣奕华材料科技有限公司 Waterborne polyurethane coating agent and preparation method and application thereof
CN111560210A (en) * 2020-04-16 2020-08-21 江苏斯迪克新材料科技股份有限公司 Antifog medical isolation face guard of wear-type high definition
CN112194775A (en) * 2020-09-29 2021-01-08 深圳市科汇泰科技有限公司 Water-based ultraviolet-curing polyurethane oligomer, preparation method thereof and ultraviolet-curing long-acting antifogging coating
CN112280280A (en) * 2020-09-21 2021-01-29 江苏鑫易达新材料科技有限公司 Antifogging surface TPU film for automobile film and preparation method thereof
CN113061391A (en) * 2021-03-29 2021-07-02 光易科技(无锡)有限公司 Radiation-cured antifogging coating composition and film and preparation method thereof
CN114196281A (en) * 2021-12-10 2022-03-18 江南大学 Method for preparing antifogging transparent coating by modified silane coupling agent and hydrophilic copolymer
CN114350192A (en) * 2021-02-01 2022-04-15 中南林业科技大学 Coating with hydrophilic self-cleaning capability and preparation method thereof
CN115433341A (en) * 2022-09-08 2022-12-06 黎明化工研究设计院有限责任公司 Hydrophilic urethane acrylate, hydrophilic trifunctional acrylate, and preparation methods and applications thereof
CN115505325A (en) * 2022-03-22 2022-12-23 武汉中科先进材料科技有限公司 Self-repairing self-cleaning dual-curing coating for photovoltaic glass and preparation method thereof

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CN102816515A (en) * 2012-08-14 2012-12-12 江苏大学 Aqueous silicon dioxide-fluorinated acrylate polyurethane ultraviolet-curing coating, preparation method and application thereof
CN105038430A (en) * 2015-08-26 2015-11-11 太仓市金新涂料有限公司 Super-hydrophilic anti-fogging coating
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Cited By (16)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN109868025A (en) * 2019-02-27 2019-06-11 江西省龙海化工有限公司 A kind of preparation method of the super hydrophilic anti-fog coating of waterborne normal-temperature self-crosslinking
CN110903459A (en) * 2019-11-25 2020-03-24 重庆沥智路桥工程有限公司 Hydroxyl-terminated polyurethane methacrylic resin, preparation method and application thereof
CN110903459B (en) * 2019-11-25 2022-06-07 重庆沥智路桥工程有限公司 Hydroxyl-terminated polyurethane methacrylic resin, preparation method and application thereof
CN111057210A (en) * 2019-12-31 2020-04-24 阜阳欣奕华材料科技有限公司 Waterborne polyurethane coating agent and preparation method and application thereof
CN111560210A (en) * 2020-04-16 2020-08-21 江苏斯迪克新材料科技股份有限公司 Antifog medical isolation face guard of wear-type high definition
CN111560210B (en) * 2020-04-16 2021-11-16 江苏斯迪克新材料科技股份有限公司 Antifog medical isolation face guard of wear-type high definition
CN112280280A (en) * 2020-09-21 2021-01-29 江苏鑫易达新材料科技有限公司 Antifogging surface TPU film for automobile film and preparation method thereof
CN112194775A (en) * 2020-09-29 2021-01-08 深圳市科汇泰科技有限公司 Water-based ultraviolet-curing polyurethane oligomer, preparation method thereof and ultraviolet-curing long-acting antifogging coating
CN114350192A (en) * 2021-02-01 2022-04-15 中南林业科技大学 Coating with hydrophilic self-cleaning capability and preparation method thereof
CN114350192B (en) * 2021-02-01 2023-01-06 中南林业科技大学 Coating with hydrophilic self-cleaning capability and preparation method thereof
CN113061391B (en) * 2021-03-29 2022-03-18 光易科技(无锡)有限公司 Radiation-cured antifogging coating composition and film and preparation method thereof
CN113061391A (en) * 2021-03-29 2021-07-02 光易科技(无锡)有限公司 Radiation-cured antifogging coating composition and film and preparation method thereof
CN114196281A (en) * 2021-12-10 2022-03-18 江南大学 Method for preparing antifogging transparent coating by modified silane coupling agent and hydrophilic copolymer
CN115505325A (en) * 2022-03-22 2022-12-23 武汉中科先进材料科技有限公司 Self-repairing self-cleaning dual-curing coating for photovoltaic glass and preparation method thereof
CN115433341A (en) * 2022-09-08 2022-12-06 黎明化工研究设计院有限责任公司 Hydrophilic urethane acrylate, hydrophilic trifunctional acrylate, and preparation methods and applications thereof
CN115433341B (en) * 2022-09-08 2024-01-05 黎明化工研究设计院有限责任公司 Hydrophilic polyurethane acrylate, hydrophilic trifunctional acrylate and preparation method and application thereof

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