CN1321164C - Lyophilic high-molecular antifogging coating and preparing method thereof - Google Patents
Lyophilic high-molecular antifogging coating and preparing method thereof Download PDFInfo
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- CN1321164C CN1321164C CNB03129409XA CN03129409A CN1321164C CN 1321164 C CN1321164 C CN 1321164C CN B03129409X A CNB03129409X A CN B03129409XA CN 03129409 A CN03129409 A CN 03129409A CN 1321164 C CN1321164 C CN 1321164C
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- monomer
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- methyl
- fog coating
- acrylate
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Abstract
The present invention relates to antifogging paint which is composed of hydrophilic polymer materials. In the prior art, the paint has the disadvantages of high cost, short antifogging service life, bad cohesive force of the paint and a base material, etc. The present invention uses the hydrophilic polymer materials, a solidifying agent and a curing accelerator to form the antifogging paint according to certain components; the antifogging paint has the advantage of convenient preparation and overcomes the disadvantages of the prior art. The hydrophilic polymer materials are obtained by the polymerization of a nonionic surface active agent (methyl) acrylic ester type monomer, an N-vinyl pyrrolidine, and (methyl) acrylic acid or/ and a (methyl) acrylic ester monomer.
Description
Technical field
The present invention relates to a kind of hydrophilic macromolecule anti-fog coating and preparation method thereof.
Background technology
Long-pending mist more and more causes people's attention on the residuite, gently then makes troubles to people's life, and is heavy then influence the normal operation of the vehicles, and then brings influence to industrial production, economic activity.The research of at present relevant such antifog material increases.Past, simple mirror was antifog, install electricradiator usually at the mirror back side additional and drive illiteracy mist moisture, but wet fogs such as similar swimming goggle, glasses, diving mask shrouds, way is very few; If car light, the wet fog of lightings such as pilot lamp can't effectively be prevented and treated, and will produce very disadvantageous consequence.
Reports such as Zhang Chunxue, by MMA, BMA, HEMA and little amount of crosslinking agent, N, the coating that the polymerization of N-methylene radical diene acid amides constitutes have well anti-fog effect.Li Xuefeng etc. are with hydroxyethyl methylacrylate, the methacrylic acid macrogol ester, acrylate copolymer adds little amount of crosslinking agent (HMMM, ethylene glycol ethyl ethers thiazolinyl dimethylsilane) and tensio-active agent (polyoxygenated alkane ether, alkyl benzene sulphonate (ABS) etc.) constitute anti-fog coating.Nof Corp. is through exploring, on glass, resin, frosting, be coated with earlier organic superoxide bottom, be coated with the high density polymer of hydrophilic radicals such as sulfonic group or hydroxy again, form firm Chemical bond, realized the antifog New Machining Technology of semipermanent.
Aforesaid method all has certain anti-fog effect, but each method all has certain deficiency, and the method that has is volatile.Behind the hydrophilic macromolecule water uptake that has, not only anti-fog performance descends, and causes the film be full of cracks simultaneously owing to swelling is softening, therefore must chemically crosslinked.Market requirement exploitation is applicable to low cost, the long-life anti-fog coating on the matrix such as glass, transparent resin for this reason.
Summary of the invention
The purpose of this invention is to provide a kind of low cost, long-life anti-fog coating.
The preparation method who the purpose of this invention is to provide a kind of low cost, long-life anti-fog coating.
The curing that the purpose of this invention is to provide a kind of low cost, long-life anti-fog coating.
Hydrophilic macromolecule anti-fog coating of the present invention is by hydrophilic high molecular material, and solidifying agent, curing catalyst are formed, and their component is:
Hydrophilic high molecular material: 15～60wt%
Solidifying agent: 2.0～20wt%
Curing catalyst: 0.1～5.0wt%
Solvent: 30～80wt%
Except above-mentioned component, also coating component routinely adds an amount of flow agent, and oxidation inhibitor etc. at room temperature mix and can use.
Above-mentioned hydrophilic high molecular material is: ω-terminal hydroxy group nonionogenic tenside (methyl) acrylic ester monomer (I) and (methyl) vinylformic acid or and the multipolymer of (methyl) acrylate (II) of hydroxyl; I, the structural formula of II is as follows:
(I)
R
2＝
*_CH
2-CH
2-O_
mR m＝1～40
or R＝-C
n′H
2n′+1 n′＝1～22
R
1Be hydrogen atom or methyl
R
3For hydrogen atom or hydroxyl contain a alkyl to four carbon.
(III)
The monomer of hydrophilic high molecular material of the present invention comprises: (methyl) acrylate of nonionogenic tenside, the N-vinyl pyrrolidone, (methyl) vinylformic acid or, (methyl) acrylate with hydroxyl, solidifying agent, curing catalyst, solvent are used to prepare coating and solidify.
Monomer and other component are following listed:
ω-terminal hydroxy group nonionogenic tenside (methyl) acrylate (I), as ω-terminal hydroxy group dodecanol oxyethyl group (n=4) methacrylic ester, ω-terminal hydroxy group modification alkylphenol oxyethyl group (n=9) acrylate, ω-terminal hydroxy group polyepoxyethane addition oleyl alcohol (n=20) acrylate etc.
(methyl) vinylformic acid or and (methyl) acrylate (II) of hydroxyl, as methacrylic acid, vinylformic acid, methacrylic acid (2-hydroxyethyl) ester, vinylformic acid (2-hydroxyethyl) ester, vinylformic acid (3-hydroxypropyl) ester, methacrylic acid (3-hydroxypropyl) ester etc.
Hydrophilic monomer (IV), as (methyl) acrylamide, (methyl) vinylformic acid N, N-dimethyl amido ethyl ester or its analogue.
(methyl) acrylate (V), as (methyl) methyl acrylate, (methyl) ethyl propenoate, (methyl) butyl acrylate etc.
Solidifying agent such as trimeric cyanamide and etherification derivative, amino alcohol, vulkacit H, urea etc. are as three butoxymethyl trimeric cyanamides, six butoxymethyl trimeric cyanamides, the trimethoxy methyl melamine, HMMM, amino alcohol, vulkacit H, one or more in the urea etc.
Curing catalyst is acid or sour salt, as sulfuric acid, hydrochloric acid, chlorsulfonic acid, and tosic acid, Hydrogen bromide, one or more in the ammonium salt of acids such as perchloric acid or acid.
Solvent refers to dissolve the solvent of above-mentioned multipolymer, the alcohol ether kind solvent all can, as ethylene glycol monomethyl ether, ethylene glycol monoethyl ether, propylene glycol monomethyl ether, dihydroxypropane single-ether, diethylene glycol monomethyl ether, glycol ether list ether etc.
Above-mentioned multipolymer and solidifying agent, curing catalyst are formed masking liquid, form the good anti-fog and antifrost coating with certain cohesive strength through the heating after fixing, this coating can produce good antistatic effect simultaneously.
Hydrophilic high molecular material of the present invention also can be ω-terminal hydroxy group nonionogenic tenside (methyl) acrylate monomer I with
(methyl) vinylformic acid or and (methyl) acrylate monomer II of hydroxyl and the multipolymer of N-vinyl pyrrolidone III.
The present invention also can be above-mentioned monomer I, II and hydrophilic monomer IV multipolymer, and the structure of hydrophilic monomer IV is as follows:
(IV)
R
1Be hydrogen atom or methyl
R
4For amino or contain an amino alkyl to four carbon
Hydrophilic monomer IV is as (methyl) acrylamide, (methyl) vinylformic acid N, and the adding of monomer I V such as N-dimethyl amido ethyl ester or its analogue can increase the anti-fog and antifrost life-span.
The present invention also can be the multipolymer of above-mentioned monomer II, III and (methyl) acrylate monomer V, (methyl) acrylate monomer is as (methyl) vinylformic acid formic acid, (methyl) ethyl propenoate, (methyl) butyl acrylate etc. can be selected any one or several combinations.The adding of monomer V can go into to increase the adhesive power of coating.The structure of (methyl) acrylate monomer V is as follows:
R
1Be hydrogen atom or methyl
R
5It is a alkyl to four carbon.
Hydrophilic high molecular material is any three kinds of monomeric quaternarys combinations among monomer II and monomer I, III, IV, the V, that is: I+II+III+IV, II+III+IV+V etc.
(methyl) acrylate of nonionogenic tenside is ω among the present invention--the terminal hydroxy group nonionogenic tenside, and as ω-terminal hydroxy group dodecanol oxyethyl group (n=4) methacrylic ester etc.
Above-mentioned nonionogenic tenside (methyl) acrylate is better with ω-terminal hydroxy group dodecanol oxyethyl group (n=4) methacrylic ester.
(methyl) vinylformic acid or and (methyl) acrylate II monomer of hydroxyl, as vinylformic acid, methacrylic acid (2-hydroxyethyl) ester, vinylformic acid (3-hydroxypropyl) ester etc.The acrylate that is preferably vinylformic acid or vinylformic acid and hydroxyl share.
Solidifying agent is trimeric cyanamide and etherification derivative, as three butoxymethyl trimeric cyanamides etc., with three butoxy trimeric cyanamides for well.
Curing catalyst is acid or sour salt, as tosic acid etc., with tosic acid for well.
The hydrophilic high molecular material preparation method is as follows:
In the reaction vessel that the agitator thermometer is housed, drop into solvent and comonomer, monomer is 1 with the weight of solvent ratio: (2-5), under the logical nitrogen, add the radical polymerization initiator of amount of monomer 0.1～3.0wt%, polymerization is 6～10 hours under 60～80 ℃ of temperature, cools off standby.The solidifying agent of adding component amount of the present invention and curing catalyst etc. promptly become anti-fog coating of the present invention during use.Various monomeric add-ons are:
I： 20～80wt％
II： 20～80wt％
III：20～80wt％
If during copolymerization mode I+II+III of the present invention, various monomeric add-ons are:
I： 10～80wt％
II： 10～80wt％
III：10～80wt％。
If copolymerization mode I+II+IV of the present invention (or V), during II+III+IV (or V), various monomeric add-ons are:
I： 10-80wt％；
II： 10-80wt％；
III：10-80wt％。
IV： 10-20wt％；
V： 10-20wt％。
According to content of the present invention, above-mentioned monomeric copolymerization mode is: I+II, II+III, I+II+III, I+II+IV (or V), II+III+IV (or V).
Above-mentioned initiator add-on is better with 0.1-0.5wt%.Initiator is the prior art initiator, as: ketone peroxide, diacyl peroxide, azo-compound, hydroperoxide are crossed acid alkyl ester etc.
Terminal hydroxy group nonionogenic tenside and acrylate derivative esterification can obtain monomer ω--preparation of terminal hydroxy group nonionogenic tenside (methyl) acrylate be with etc. the ω of gram molecular weight--, and this reaction is prior art.
Antifog and anti-cream composition of the present invention can be coated on the transparent substrate as matrix, and on synthetic resins or glasswork, warm air drying is removed and desolvated, and makes coating curing.The matrix of resin is polymethacrylate for example, polycarbonate, poly-terephthaldehyde's ester glycol ester, polystyrene etc.
Glass after applying and plastics are placed in the baking oven made coating curing in 30-180 minute, in above-mentioned scope, adjust condition of cure according to the end-use and the characteristic of glass and plastics 50-120 ℃ of heating.
The method of coating can adopt brushing according to coated matrix shape, spraying or dip-coating.
The thickness of coating is advisable with 1-30 μ m.
In the present composition preferably solvent be ethylene glycol monomethyl ether, ethylene glycol monoethyl ether is adjusted the viscosity of composition when the 25C about 100cps (centipoise), so that coating has satisfied surface characteristic with solvent.If the anti-fog coating viscosity of using is too high, the shortcoming that is shown is the wrinkling or flake of coatingsurface.
Antifog principle of the present invention is to utilize resin coating to form super hydrophilic surface, and its contact angle to water is diminished, and does not form the small globule at surface spreading for moisture film as thin as a wafer,, the radiation that prevents to overflow reaches antifogging action.
Of the present invention filming done following test:
The film adhesive test is measured film adhesive according to the relevant clauses and subclauses of State Standard of the People's Republic of China GB1720-79 film adhesive assay method.Represent with level by the integrated degree evaluation of filming that circle rolls in the cut scope.
The water-resistance property of coating test, the immersion laboratory method.It is in the distilled water of 40C that the sample that scribbles anti-fog coating is immersed temperature, soaks taking-up after 240 hours, blots with filter paper, as has filmed and peel off, and wrinkling is defective.
Anti-fog performance: place 80C water vapour top after 10 seconds in a sample coatings face that scribbles anti-fog coating, the mist formation of visual inspection coating.
Above-mentioned test result all meets existing standard, and some indexs have exceeded existing standard, and it is easy to prepare to prove absolutely that coating of the present invention has, and cost is low, and the life-span is long, characteristics such as anti-fog and antifrost excellent property.
Embodiment
Embodiment 1
In the 120g ethylene glycol monomethyl ether, add 18g ω-terminal hydroxy group dodecanol oxyethyl group (n=4) methacrylic ester, 6g methacrylic acid (2-hydroxyethyl) ester, 6g methacrylic acid and 0.15g benzoyl peroxide stir dissolving fully, 60C polymerization 6 hours.After the cooling, add 4.5g three butoxymethyl trimeric cyanamides, 0.3g tosic acid and 0.6g flow agent, it is standby to stir.
In above-mentioned coating, add the 0.3g tosic acid, mix.Described coating composition is sprayed on the surface of polycarbonate plate, preliminary drying is 0.5 hour in the 50C baking oven, solidifies 1 hour so that paint solidification at 120C then.
Example 2-example 6 use-cases 1 method, the different composition, component has obtained the anti-fog coating of superperformance, sees the following form.
| 1 2 3 4 5 6 7 | |||
| Masking liquid is formed | Multipolymer is formed | ω-HDEMA HEMA NVP MAA AA MMA ME BPO | 18 6 12 12 3 9 6 6 9 9 6 18 12 12 9 15 6 6 3 6 9 6 6 3 3 3 3 120 120 120 120 120 120 120 0.15 0.15 0.15 0.15 0.15 0.15 0.15 |
| BMCN flow agent TPS | 4.5 4.5 4.5 4.5 4.5 4.5 4.5 0.6 0.6 0.6 0.6 0.6 0.6 0.6 0.3 0.3 0.3 0.3 0.3 0.3 0.3 | ||
| Character | The anti-fog effect of transparency sticking power water tolerance | Carefully get well carefully 3 grades of 1 grade of 2 grades of 1 grade of 3 grades of 1 grade of 1 grade＜240h＜240h＞240h＞240h＜240h＜240h＞240h＞10s＞10s＞10s＞10s＜10s＞10s＞10s | |
Writing a Chinese character in simplified form title in the table is expressed as follows:
ω-HDEMA: ω-terminal hydroxy group dodecanol oxyethyl group (n=4) methacrylic ester
The NVP:N-vinyl pyrrolidone
HEMA: methacrylic acid (2-hydroxyethyl) ester
MAA: methacrylic acid
AA: acrylamide
The MMA:(methyl) methyl acrylate
ME: ethylene glycol monomethyl ether
BPO: benzoyl peroxide
BMCN: three butoxymethyl trimeric cyanamides
TPS: tosic acid
Flow agent: acrylate interpolymer
Claims (15)
1. hydrophilic macromolecule anti-fog coating by hydrophilic macromolecule, solidifying agent, curing catalyst, solvent composition, is characterized in that their component is:
Hydrophilic high molecular material: 15～60wt%;
Solidifying agent: 2.0～20w
Curing catalyst: 0.1～5.0wt%;
Solvent: 30～80wt%;
Above-mentioned hydrophilic high molecular material is: the acrylate of ω-terminal hydroxy group nonionogenic tenside or methyl acrylic ester monomer (I) and (methyl) vinylformic acid or, with the acrylate of hydroxyl or the multipolymer of methacrylic ester (II), I, the structural formula of II is as follows:
(I)
R
2＝
*_CH
2-GH
2-O_ m＝1～40
R″＝-C
nH
2n+1 n＝8～18
Or R=-C
n' H
2n '+1N '=1～22
R
1Be hydrogen atom or methyl;
R
3For hydrogen atom or hydroxyl contain a alkyl to four carbon.
2. hydrophilic macromolecule anti-fog coating according to claim 1 is characterized in that hydrophilic high molecular material is monomer (I) and the multipolymer of monomer (II) with N-vinyl pyrrolidone (III), and the structural formula of III is as follows:
(III)
3. hydrophilic macromolecule anti-fog coating according to claim 1 is characterized in that hydrophilic high molecular material is the multipolymer of monomer I, II and hydrophilic monomer (IV), and the structure of hydrophilic monomer (IV) is as follows:
(IV)
R
1Be hydrogen atom or methyl;
R
4For amino or contain an amino alkyl to four carbon.
4. hydrophilic macromolecule anti-fog coating according to claim 1, it is characterized in that hydrophilic high molecular material is the multipolymer of monomer I, II and acrylate or methacrylate monomer (V), the structure of acrylate or methacrylate monomer (V) is as follows:
R
1Be hydrogen atom or methyl;
R
5It is a alkyl to four carbon.
5. according to claim 1 or 2 or 3 or 4 described hydrophilic macromolecule anti-fog coatings, it is characterized in that (methyl) vinylformic acid or and the acrylate of hydroxyl or the acrylate that methacrylate monomer (II) is vinylformic acid or vinylformic acid and hydroxyl share.
6. hydrophilic macromolecule anti-fog coating according to claim 5 is characterized in that the acrylate of ω one terminal hydroxy group nonionogenic tenside or methacrylic ester are ω one terminal hydroxy group dodecanol oxyethyl group n=4 methacrylic esters.
7. hydrophilic macromolecule anti-fog coating according to claim 1 is characterized in that solidifying agent is trimeric cyanamide and etherification derivative.
8. hydrophilic macromolecule anti-fog coating according to claim 1 is characterized in that curing catalyst is acid or sour salt.
9. hydrophilic macromolecule anti-fog coating according to claim 2, the preparation method who it is characterized in that hydrophilic high molecular material in this anti-fog coating is in thermometric reactor is arranged, drop into monomer and solvent, drop into monomeric logical simultaneously nitrogen, and adding radical initiator, under the 60-80 ℃ of temperature polymerization 6-10 hour, cooling got final product; The weight ratio of monomer and solvent is 1: (2-5), the add-on of initiator is the 0.1-3.0wt% of amount of monomer, and various monomeric add-ons are as follows:
I：20-80wt％；
II：20-80wt％；
III:20-80wt%; Each monomer add-on sum is 100%.
10. hydrophilic macromolecule anti-fog coating according to claim 2 is characterized in that various monomeric add-ons are as follows:
I：10-80wt％；
II：10-80wt％；
III:10-80wt%; Each monomer add-on sum is 100%.
11. hydrophilic macromolecule anti-fog coating according to claim 6 is characterized in that the ω-terminal hydroxy group nonionogenic tenside monomer of gram molecular weights such as the ω-acrylate of terminal hydroxy group nonionogenic tenside or the preparation method of methacrylic ester are and acrylic acid derivative esterification obtain.
12. hydrophilic macromolecule anti-fog coating according to claim 1, the solvent that it is characterized in that this coating are ethylene glycol monomethyl ether or ethylene glycol monoethyl ether.
13., it is characterized in that this coating is to be coated on the transparent substrate after the drying when using according to the using method of claim 1 hydrophilic macromolecule anti-fog coating, be positioned over 50-120 ℃ of heating 30-180 minute down, coating curing is got final product.
14. the using method of hydrophilic macromolecule anti-fog coating according to claim 1, the coating method that it is characterized in that this coating are brushings, or spraying, or dip-coating.
15. the using method of hydrophilic macromolecule anti-fog coating according to claim 1 is characterized in that the thickness that anti-fog coating is coated on the residuite is 1-30um.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB03129409XA CN1321164C (en) | 2003-06-20 | 2003-06-20 | Lyophilic high-molecular antifogging coating and preparing method thereof |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CNB03129409XA CN1321164C (en) | 2003-06-20 | 2003-06-20 | Lyophilic high-molecular antifogging coating and preparing method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN1472268A CN1472268A (en) | 2004-02-04 |
| CN1321164C true CN1321164C (en) | 2007-06-13 |
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|---|---|---|---|
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|---|---|---|---|---|
| CN100341926C (en) * | 2005-12-07 | 2007-10-10 | 浙江大学 | Method for preparing antifogging plastic film by surface coating process |
| CN100425436C (en) * | 2005-12-07 | 2008-10-15 | 浙江大学 | Method for preparing antifogging plastic film by blend reshaping process |
| CN101591494B (en) * | 2009-07-03 | 2011-08-31 | 北京瑞博奥生物科技有限公司 | Antifogging coating, special antifogging coating composition and antifogging product thereof |
| CN102086348B (en) * | 2010-11-26 | 2013-01-09 | 上海旺俊化工有限公司 | Polyurethane cured acrylic resin anti-fogging and abrasion-resistant paint and preparation method thereof |
| CN102167945A (en) * | 2010-11-29 | 2011-08-31 | 湖南晟通科技集团有限公司 | Hydrophilic paint and preparation method thereof |
| CN102146242B (en) * | 2011-01-18 | 2012-11-14 | 深圳市嘉卓成科技发展有限公司 | High-performance antifog coating and production method and using method thereof |
| CN104212292B (en) * | 2014-08-27 | 2017-02-01 | 深圳市安品有机硅材料有限公司 | Antifogging paint, antifogging coating and preparation method of antifogging paint |
| CN104356724B (en) * | 2014-12-10 | 2017-01-04 | 李永志 | A kind of preparation method of hydrophilic reflection paint |
| CN104558661A (en) * | 2014-12-18 | 2015-04-29 | 盐城工学院 | Antifogging resin optical lens and preparation method thereof |
| CN105315735B (en) * | 2015-11-04 | 2018-05-11 | 上海乘鹰新材料有限公司 | The hydrophilic antifogging coating composition of photo-thermal dual curable |
| JP7027034B2 (en) * | 2016-10-14 | 2022-03-01 | 株式会社Adeka | Anti-fog paint compositions and articles |
| CN106750235B (en) * | 2017-01-24 | 2019-04-12 | 上海维凯光电新材料有限公司 | The preparation method of quaternary hydrophily UV-cured resin |
| 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 |
| RU2762179C2 (en) * | 2017-10-04 | 2021-12-16 | ЭмСиЭс ИНДАСТРИЗ, ИНК. | Anti-mist coating and process of application thereof |
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| CN1472268A (en) | 2004-02-04 |
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