CN102850924B - Antifogging coating long in antifogging life - Google Patents
Antifogging coating long in antifogging life Download PDFInfo
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- CN102850924B CN102850924B CN201210355296.XA CN201210355296A CN102850924B CN 102850924 B CN102850924 B CN 102850924B CN 201210355296 A CN201210355296 A CN 201210355296A CN 102850924 B CN102850924 B CN 102850924B
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Abstract
The invention relates to antifogging coating long in antifogging life. The antifogging coating is formed by matching antifogging resin and closed type isocyanate curing agent. The antifogging resin is prepared by utilizing 10-50wt% of acrylate monomer, 1-40wt% of vinyl monomer containing nitrogen atoms, 1-10wt% of modified surfactant, 0.1-5wt% of trigger and the balance hydrophilic solvent as raw materials, adding the hydrophilic solvent into a reactor, heating to 50-140 DEG C, mixing and stirring the raw materials uniformly, dropping the mixture into the solvent at uniform speed for 2-5 hours, and preserving heat to react for 1-3 hours after dropping. The modified surfactant is formed by grafting surfactant containing sulfonic acid group, sulfuric acid group or carboxylic acid perssad with (methyl) glycidyl acrylate monomers according to the mole ratio of 0.5-2:1. The antifogging coating is long in antifogging life, waterproof, anti-ageing and excellent in comprehensive performance.
Description
Technical field
The present invention relates to the lasting anti-fog coating of a kind of antifog property, be specially adapted to the antifog of transparent plastics material and glass material etc.
Background technology
From the seventies in last century, there are a large amount of companies and research institution to carry out the exploitation of anti-fog coating, particularly Japanese firm abroad and occur a lot of patents in the nineties, invented various anti-fog coatings.In the document and patent of open report, anti-fog coating performance antifogging action is mainly because tensio-active agent is enriched in film coated surface after film forming, form super hydrophilic molecular layer, make water vapour there is very large contact angle at coating surface, water vapour can not condense into the globule, thereby reaches antifog effect.But As time goes on, its tensio-active agent can be dissolved in the water of film coated surface, along with wiping of water vapour, and being pulled away slowly, thereby anti-fog effect can be more and more a little less than, antifog persistence is poor.A lot of products both domestic and external are all difficult to reach good antifog persistence at present.
Summary of the invention
The object of the invention is: a kind of antifog property improvement and ageing-resistant, water-fast lasting anti-fog coating of antifog property of continuing is provided, be mainly used in transparent plastic substrate surface, for example polycarbonate plate (PC plate), acrylic board (PMMA plate) and glass baseplate surface, such as minute surface etc.
The technical scheme that realizes the object of the invention is: the lasting anti-fog coating of a kind of antifog property, it is characterized in that, and in case coordinating with Blocked Isocyanate Curing Agents as main film-forming resin, mist characteristic resin forms anti-fog coating;
Described antifog characteristic resin be using the vinyl monomer of 10～50wt% acrylate monomer, 1～40wt% nitrogen atom, the tensio-active agent of 1～10wt% modification, 0.1～5wt% initiator, surplus as hydrophilic solvent is as raw material, in reaction vessel, add hydrophilic solvent, be warming up to 50～140 ℃, after the tensio-active agent of above-mentioned monomer, modification and initiator are mixed, at the uniform velocity be added drop-wise in solvent, time for adding is 2～5 hours, after dropping finishes, insulation reaction 1～3 hour, makes;
Wherein, the tensio-active agent of modification is for after containing the tensio-active agent of sulfonic group, sulfate or hydroxy-acid group, 0.5～2:1 mixes in molar ratio with (methyl) glycidyl acrylate monomer, add proper catalyst Mono-n-butyltin, be warming up to 80～180 ℃ and be incubated that grafting in 3～3.5 hours forms.
Above-mentioned anti-fog coating is by the antifog characteristic resin of 20～50wt%, 2～15wt% Blocked Isocyanate Curing Agents, and 0.01～2.0wt% catalyzer, surplus is that thinner forms; Described thinner is one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone; Described catalyzer is Mono-n-butyltin.
In above-mentioned anti-fog coating, described thinner is one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone.
In above-mentioned anti-fog coating, described Blocked Isocyanate Curing Agents is tolylene diisocyanate (being called for short TDI), hexamethylene diisocyanate (being called for short HDI) or the isophorone diisocyanate (being called for short IPDI) of ketone, ethyl 3-oxobutanoate or Diacetylmonoxime encapsulant end-blocking in hexanolactam, phenol, cresols, m-nitrophenol, para-chlorophenol, pyrocatechol, diethyl malonate, acetyl.
In above-mentioned anti-fog coating, vinyl monomer for the preparation of the nitrogen atom of described antifog characteristic resin is (methyl) acrylamide, N methacrylamide, N, N-DMAA, N-ethyl acrylamide, N, N-diethyl acrylamide, N-n-propyl group acrylamide, NIPA, N, N-dimethyl pyrrolidone, N-Methyl pyrrolidone, N, N '-dimethylaminoethyl (methyl) acrylamide, N, one or more in N '-dimethyl aminopropyl (methyl) acrylamide and N-ethyl-2-pyrrolidone.
In above-mentioned anti-fog coating, for the preparation of the acrylate monomer of described antifog characteristic resin, be at least two kinds in (methyl) vinylformic acid, (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, Isooctyl acrylate monomer, (methyl) ethyl propenoate.
In above-mentioned anti-fog coating, for the preparation of the hydrophilic solvent of described antifog characteristic resin, be one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone; Initiator is a kind of in benzoyl peroxide, lauroyl peroxide, isopropyl benzene hydroperoxide, tertbutyl peroxide, di-t-butyl peroxide, dicumyl peroxide, peroxidized t-butyl perbenzoate, peroxidation trimethylacetic acid tertiary butyl ester, methylethyl ketone peroxide, cyclohexanone peroxide, Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), di-isopropyl peroxydicarbonate, di-cyclohexylperoxy dicarbonate.
In above-mentioned anti-fog coating, is C for the preparation of the tensio-active agent of modification in described antifog characteristic resin containing sulfonic group tensio-active agent
10-20alkyl group sulfonic acid, aromatic hydrocarbons sulfonic acid, alkylated aromatic sulfonic acid, alkyl sulfo-succinic acid or alpha-olefin sulfonic acid; Sulfur acid based surfactants used is C
10-20alkyl group sulfuric acid (ester), C
10-20alkenyl sulfuric ester or C
10-20alkyl group ether sulfuric acid (ester); The tensio-active agent of hydroxy-acid group used is C
8-26lipid acid.
Technique effect of the present invention is: the anti-fog coating of technical solution of the present invention, the antifog characteristic resin of its main film-forming resin is with acrylate monomer, the tensio-active agent copolymerization of nitrogen atom vinyl monomer and modification forms, wherein, acrylic ester monomer is the agent structure of characteristic resin, the tensio-active agent of nitrogen atom vinyl monomer and modification provides the hydrophilic structure of characteristic resin, like this, be more conducive to improve water vapour at the contact angle of film coated surface, thereby make water vapour can not condense into the globule, improve anti-fog effect, and the tensio-active agent of process graft modification is when anti-fog coating film forming, the tensio-active agent of modification can with the matrix resin structure crosslinking curing of anti-fog coating, tensio-active agent is not dissolved in water, overcome in prior art because surfactant dissolves is in the water of film coated surface, along with wiping of water vapour, and the shortcoming being pulled away slowly, so just kept good antifog persistence, the water tolerance of while resin and ageing resistance be very excellent (in Table 11) all.
Embodiment
Below in conjunction with embodiment, the present invention is done to further specific descriptions, but be not limited to this.
Embodiment raw materials is unless otherwise indicated commercially available industrial goods, can buy by commercial channel.
(1) preparation of the tensio-active agent of modification
The tensio-active agent of modification of the present invention is for after containing the tensio-active agent of sulfonic group, sulfate or hydroxy-acid group, 0.5～2:1 mixes in molar ratio with (methyl) glycidyl acrylate monomer, add proper catalyst Mono-n-butyltin, be warming up to 80～180 ℃ and be incubated that grafting in 3～3.5 hours forms.
Embodiment 1
1. composition of raw materials is in Table 1.
Table 1
2. preparation technology
Three kinds of raw materials in above-mentioned formula are joined in reaction flask, be warming up to 120 ℃, be incubated after 3 hours, make the tensio-active agent of modification, save backup.
Embodiment 2
1. composition of raw materials is in Table 2.
Table 2
2. preparation technology
Three kinds of raw materials in above-mentioned formula are joined in reaction flask, be warming up to 130 ℃, be incubated after 3 hours, make the tensio-active agent of modification, save backup.
Embodiment 3
1. composition of raw materials is in Table 3.
Table 3
2. preparation technology
Three kinds of raw materials in above-mentioned formula are joined in reaction flask, be warming up to 150 ℃, be incubated after 3 hours, make the tensio-active agent of modification, save backup.
(2) prepare antifog characteristic resin
Antifog characteristic resin of the present invention be using the vinyl monomer of 10～50wt% acrylate monomer, 1～40wt% nitrogen atom, the tensio-active agent of 1～10wt% modification, 0.1～5wt% initiator, surplus as hydrophilic solvent is as raw material.
Embodiment 4
1. composition of raw materials is in Table 4.
Table 4
2. preparation technology
In reaction vessel, add hydrophilic solvent, be warming up to 80 ℃, after the tensio-active agent of monomer, modification and initiator are mixed, at the uniform velocity be added drop-wise in solvent, time for adding is 4 hours, after dropping finishes, 80 ℃ of insulation reaction 1 hour, make the antifog Resin A of characteristic, save backup.
Embodiment 5
1. composition of raw materials is in Table 5.
Table 5
2. preparation technology
In reaction vessel, add hydrophilic solvent, be warming up to 120 ℃, after the tensio-active agent of monomer, modification and initiator are mixed, at the uniform velocity be added drop-wise in solvent, time for adding is 3 hours, after dropping finishes, 120 ℃ of insulation reaction 1 hour, make the antifog resin B of characteristic, save backup.
Embodiment 6
1. composition of raw materials is in Table 6.
Table 6
2. preparation technology
In reaction vessel, add hydrophilic solvent, be warming up to 130 ℃, after the tensio-active agent of monomer, modification and initiator are mixed, at the uniform velocity be added drop-wise in solvent, time for adding is 4 hours, after dropping finishes, 130 ℃ of insulation reaction 3 hours, make the antifog resin C of characteristic, save backup.
(3) prepare anti-fog coating and model
Anti-fog coating of the present invention is by the antifog characteristic resin of 20～50wt%, 2～15wt% Blocked Isocyanate Curing Agents, and 0.01～2.0wt% catalyzer, surplus is that thinner forms; Described thinner is one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone; Described catalyzer is Mono-n-butyltin.
Embodiment 7
1. anti-fog coating formula is in Table 7.
Table 7
2. prepare anti-fog coating and model
According to above-mentioned formula, each component is mixed and prepares coating, be then sprayed at clear polycarbonate plate (hereinafter to be referred as PC plate) above, at 100 ℃, toast the model obtaining for 20 minutes and preserve the standby use that detects.
Embodiment 8
1. anti-fog coating formula is in Table 8.
Table 8
2. prepare anti-fog coating and model
According to above-mentioned formula, each component is mixed and prepares coating, be then sprayed on PC plate, at 120 ℃, toast the model obtaining for 10 minutes and preserve the standby use that detects.
Embodiment 9
1. anti-fog coating formula is in Table 9.
Table 9
2. prepare anti-fog coating and model
According to above-mentioned formula, each component is mixed and prepares coating, be then sprayed on PC plate, toast 35 minutes at 90 ℃, the model obtaining is preserved standby detection and is used.
Embodiment 10
1. anti-fog coating formula is in Table 10.
Table 10
2. prepare anti-fog coating and model
According to above-mentioned formula, each component is mixed and prepares coating, be then sprayed on PC plate, toast 40 minutes at 80 ℃, the model obtaining is preserved standby detection and is used.
(4) anti-fog coating Performance Detection
Coating model made in example 7～10 is carried out to performance test, and concrete testing method is as follows:
1. anti-fog performance detects: the above-mentioned model that scribbles anti-fog coating making is placed under 5 ℃ of environment, to film coated surface, exhales, as without blushing, be considered as meeting antifog requirement;
2. resistance to wiping properties: at every turn carrying out after anti-fog performance detection, with clean cotton or coil paper, water mark wiping above is complete, then proceed antifog experiment, observe the number of times of wiping in the situation that the anti-fog effect that keeps filming does not decline, more the bright resistance to wiping properties of multilist is better for wiping number of times;
3. water tolerance detects: water Dipping under room temperature environment, with coating occur the turning white length of Swelling time used, weigh its water tolerance;
4. sticking power: adopt paint film adhesion determinator according to standard GB/T/T1720-89, frame method is measured;
5. hardness: adopt pencil hardness method to measure according to standard GB/T/T6739-2006;
6. ageing-resistant performance: the mensuration of carrying out ageing resistance according to standard GB/T/T1865-1997;
Test result is listed in table 11.
Table 11
Note: comparative example is the GAF-209A/B heat embrittlement type anti-fog coating that Japanese Fujikura Kasei Co., Ltd produces, and its model preparation method and detection method are identical with embodiment 7～10.
From the test result of table 11, can find out, the antifog property of anti-fog coating of the present invention is lasting and water-fast, ageing-resistant, and excellent combination property, particularly resistance to wiping properties are obviously better than the existing anti-fog coating product of comparative example.
Claims (6)
1. the lasting anti-fog coating of antifog property, is characterized in that, in case mist characteristic resin coordinates with Blocked Isocyanate Curing Agents as main film-forming resin, forms anti-fog coating;
Described anti-fog coating is by the antifog characteristic resin of 20～50wt%, 2～15wt% Blocked Isocyanate Curing Agents, and 0.01～2.0wt% catalyzer, surplus is that thinner forms; Described thinner is one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone; Described catalyzer is Mono-n-butyltin;
Described antifog characteristic resin be using the vinyl monomer of 10～50wt% acrylate monomer, 1～40wt% nitrogen atom, the tensio-active agent of 1～10wt% modification, 0.1～5wt% initiator, surplus as hydrophilic solvent is as raw material, in reaction vessel, add hydrophilic solvent, be warming up to 50～140 ℃, after the tensio-active agent of above-mentioned monomer, modification and initiator are mixed, at the uniform velocity be added drop-wise in solvent, time for adding is 2～5 hours, after dropping finishes, insulation reaction 1～3 hour, makes;
Wherein, the tensio-active agent of modification is for after containing the tensio-active agent of sulfonic group, sulfate or hydroxy-acid group, 0.5～2:1 mixes in molar ratio with (methyl) glycidyl acrylate monomer, add catalyzer Mono-n-butyltin, be warming up to 80～180 ℃ and be incubated that grafting in 3～3.5 hours forms.
2. anti-fog coating according to claim 1, it is characterized in that, described Blocked Isocyanate Curing Agents is tolylene diisocyanate, hexamethylene diisocyanate or the isophorone diisocyanate of hexanolactam, phenol, cresols, m-nitrophenol, para-chlorophenol, pyrocatechol, diethyl malonate, ethyl 3-oxobutanoate or Diacetylmonoxime encapsulant end-blocking.
3. anti-fog coating according to claim 1, it is characterized in that, vinyl monomer for the preparation of the nitrogen atom of described antifog characteristic resin is (methyl) acrylamide, N methacrylamide, N, N-DMAA, N-ethyl acrylamide, N, N-diethyl acrylamide, N-n-propyl group acrylamide, NIPA, N, N '-dimethylaminoethyl (methyl) acrylamide, N, one or more in N '-dimethyl aminopropyl (methyl) acrylamide.
4. anti-fog coating according to claim 1, it is characterized in that, be at least two kinds in (methyl) methyl acrylate, (methyl) butyl acrylate, (methyl) Hydroxyethyl acrylate, (methyl) Propylene glycol monoacrylate, Isooctyl acrylate monomer, (methyl) ethyl propenoate for the preparation of the acrylate monomer of described antifog characteristic resin.
5. anti-fog coating according to claim 1, is characterized in that, for the preparation of the hydrophilic solvent of described antifog characteristic resin, is one or more in butyl glycol ether, propylene glycol monomethyl ether, ethylene glycol ethyl ether, Virahol, propyl carbinol, acetone, butanone; Initiator is a kind of in benzoyl peroxide, lauroyl peroxide, isopropyl benzene hydroperoxide, tertbutyl peroxide, di-t-butyl peroxide, dicumyl peroxide, peroxidized t-butyl perbenzoate, peroxidation trimethylacetic acid tertiary butyl ester, methylethyl ketone peroxide, cyclohexanone peroxide, Diisopropyl azodicarboxylate, 2,2'-Azobis(2,4-dimethylvaleronitrile), di-isopropyl peroxydicarbonate, di-cyclohexylperoxy dicarbonate.
6. anti-fog coating according to claim 1, is characterized in that, is C for the preparation of the tensio-active agent of modification in described antifog characteristic resin containing sulfonic group tensio-active agent
10-20alkyl group sulfonic acid, aromatic hydrocarbons sulfonic acid, alkylated aromatic sulfonic acid, alkyl sulfo-succinic acid or alpha-olefin sulfonic acid; Sulfur acid based surfactants used is C
10-20alkyl group sulfuric acid (ester), C
10-20alkenyl sulfuric ester or C
10-20alkyl group ether sulfuric acid (ester); The tensio-active agent of hydroxy-acid group used is C
8-26lipid acid.
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| TWI534215B (en) * | 2013-05-03 | 2016-05-21 | 精磁科技股份有限公司 | Anti-fog paste and manufacturing method of anti-fog substrate |
| CN104592850B (en) * | 2014-12-31 | 2017-06-23 | 三棵树涂料股份有限公司 | The preparation method of ultra-hydrophilic transparent antifogging coating |
| JP7027034B2 (en) * | 2016-10-14 | 2022-03-01 | 株式会社Adeka | Anti-fog paint compositions and articles |
| JP2019006891A (en) * | 2017-06-23 | 2019-01-17 | トーヨーポリマー株式会社 | Antifogging coating composition and antifogging transparent sheet using the same |
| CN107267060A (en) * | 2017-07-21 | 2017-10-20 | 江苏宏泰高分子材料有限公司 | A kind of anti-fog coating and preparation method thereof |
| CN108219063B (en) * | 2017-12-29 | 2021-01-05 | 新丰博兴聚合材料有限公司 | UV (ultraviolet) photocuring antifogging resin as well as preparation method and application thereof |
| CN108467650A (en) * | 2018-03-23 | 2018-08-31 | 苏州瑞康真空科技有限公司 | A kind of preparation method of hydrophilic antifogging material |
| EP4119625A1 (en) * | 2020-03-10 | 2023-01-18 | NOF Corporation | Antifoggant composition and anti-fog article having antifogging film formed from said composition |
| CN111423772B (en) * | 2020-05-06 | 2021-12-28 | 深圳大学 | Anti-fog and anti-fog coating and preparation method thereof |
| CN112409987B (en) * | 2020-11-24 | 2022-08-16 | 中电保力（北京）科技有限公司 | Hydrophilic antifogging agent |
| CN113416338B (en) * | 2021-07-05 | 2022-07-26 | 海南赛诺实业有限公司 | Anti-fog easy-uncovering coating film and preparation method thereof |
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| CN1061785A (en) * | 1990-11-27 | 1992-06-10 | 博士伦有限公司 | The surface modification of polymer articles |
| KR20030065716A (en) * | 2002-01-30 | 2003-08-09 | 주식회사 코켐 | Manufacturing anti-fog coating resin and their manufacturing method using waterborne polyurethane |
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