CN104910203A - Glass surface hydrophobic modifier and synthetic method therefor - Google Patents
Glass surface hydrophobic modifier and synthetic method therefor Download PDFInfo
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- CN104910203A CN104910203A CN201510246902.8A CN201510246902A CN104910203A CN 104910203 A CN104910203 A CN 104910203A CN 201510246902 A CN201510246902 A CN 201510246902A CN 104910203 A CN104910203 A CN 104910203A
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- glass
- glass surface
- synthetic method
- hydrophobic modifier
- surface hydrophobic
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Abstract
The invention discloses a glass surface hydrophobic modifier. S-triazine is employed as a core, and peripheral end groups are six hydrophobic alkyl end groups and a coupling group, the structural formula is shown in the specification, R1 is an alkyl group with 4-12 carbon atoms, and R2 is a methyl group or an ethyl group. The synthetic method comprises the following steps: first, ingredient preparation is carried out; section, a reaction is carried out; third, 3-aminopropyl-triethoxysilane is added and a backflow reaction is carried out; fourth, organic solvents are removed, washing is carried out, and a glass surface hydrophobic modifier is obtained. The glass surface hydrophobic modifier employs cheap and easily available cyanuric chloride as a raw material, six alkyl chains are introduced as hydrophobic end groups and an organosiloxane is introduced as a coupling end group with glass successively, hydrophobic modification of glass surfaces can be carried out in simple conditions, the contact angle of water on the surface can reach more than 90 degrees, and good hydrophobicity and glass light transmittance are achieved. The synthetic method is advantaged by cheap raw materials, mild synthesis conditions, simple technology, high yield and good application prospect.
Description
Technical field
The invention belongs to technical field of fine, be specifically related to a kind of glass surface hydrophobic modifier and synthetic method thereof.
Background technology
Glass is a kind of material widely used at present, can be used for many fields such as building, building decoration, automobile making, electronical display and photovoltaic device.The surface of simple glass is generally the water-wetted surface of high surface energy.After contacting with water, the surface energy of simple glass has larger reduction, thus can soak by water.But rough, uneven due to simple glass, there will be advancing angle after making water droplet on the surface of the simple glass tilted and laggard angle is unequal sticks.Water droplet stick situations such as can causing the light transmission of glass is poor, flash of light, pickup, affect the application of glass in fields such as automobile, building decoration, electronical display and photovoltaic devices.
Being attached on to solve water droplet the problem that glass produces, being typically employed in now the method for plated film on glass.Glass coating makes, with hydrophobic film on glass, to become Hydrophobic glass.After on the Hydrophobic glass that water droplet drops on inclination, because hydrophobic film reduces the adhesive power between glass and water droplet, thus can make water droplet rapid landing from glass under the effect of self gravitation.Present coating technique has: alumina formwork method, chemical Vapor deposition process, sol-gel method etc.Because after glass coating, its light transmission can reduce, its application in some fields can be affected; Or need to take special anti-reflection technology, such production cost turn improves.Simple glass so can be accomplished to be converted into Hydrophobic glass, the light transmission of glass is not affected again while carrying out surface of ordinary glass hydrophobically modified? here, suitable glass surface hydrophobic modifier is used just to become the key that simple glass is converted into Hydrophobic glass.
Summary of the invention
The object of the invention is to solve the problem, a kind of glass surface hydrophobic modifier is provided---s-triazine hydrophobic modifier, it with cyanuric chloride cheap and easy to get for raw material, successively introduce six alkyl chains as hydrophobic ending group and an organo-siloxane as the coupling end group with glass, glass surface hydrophobically modified can be carried out under easy condition, modified glass, the contact angle of water on its surface can reach 90
oabove, there is good hydrophobicity.The second object of the present invention is, provides the synthetic method of described glass surface hydrophobic modifier.
For achieving the above object, this invention takes following technical scheme.
A kind of glass surface hydrophobic modifier, it is characterized in that, take s-triazine as core, and peripheral end group is six hydrophobic alkyl end groups and a coupling base, and its structural formula is:
In formula:
R
1for the alkyl of 4-12 carbon;
R
2for methyl or ethyl.
For realizing above-mentioned second object, this invention takes following technical scheme.
A synthetic method for glass surface hydrophobic modifier, is characterized in that, containing following steps:
(1) component prepares
Under nitrogen atmosphere, to adding the cyanuric chloride of 1 times of molar weight, three-(2-carbalkoxy ethoxymethyl)-methylamines of 2 times of molar weights, the salt of wormwood of 4 times of molar weights and dioxane in the reactor of reflux as solvent, above-mentioned raw materials is mixed;
(2) react
The mixing raw material of step (1) is first reacted 1h under 0 DEG C of ice-water bath; Then room temperature reaction 2h; Back flow reaction 20h again;
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction
The basis of step (2) reactant adds the 3-aminopropyltrialkoxy silanes of 5 times of molar weights, continues back flow reaction 10h;
(4) remove organic solvent and wash
Pressure reducing and steaming organic solvent and dioxane and excessive 3-aminopropyltrialkoxy silanes, priority water and petroleum ether removing impurity again, obtain glass surface hydrophobic modifier---2-(3-organoalkoxysilane Propylamino)-4,6-bis--[three-(2-carbalkoxy ethoxyl methyl)-methylaminos]-[1,3,5]-triazine;
The chemical equation of described synthetic method is:
。
Further, described in step (1) three-(2-carbalkoxy ethoxymethyl)-methylamines are one of trimethyl carbinol ester in C4-C12 alcohol ester, hexamethylene alcohol ester, isooctyl alcohol ester or lauryl alcohol ester.
Further, the 3-aminopropyltrialkoxy silanes described in step (3) is the one in methoxyl group or oxyethyl group.
Positively effect of the present invention is:
(1) glass surface hydrophobic modifier of the present invention with cyanuric chloride cheap and easy to get for raw material, successively introduce six alkyl chains as hydrophobic ending group and an organo-siloxane as the coupling end group with glass, the hydrophobically modified of glass surface can be carried out under easy condition.
(2) glass adopting glass surface hydrophobic modifier of the present invention modified, transparence is unaffected, and the contact angle of water on its surface can reach 90
oabove, there is good hydrophobicity.
(3) synthetic method raw material of the present invention is cheap, synthesis condition is gentle, technique is simple, productive rate is high, has applications well prospect.
Accompanying drawing explanation
Fig. 1 is the FB(flow block) of the synthetic method of a kind of glass surface hydrophobic modifier of the present invention.
Fig. 2 is that water is at the contact angle without properties-correcting agent glass surface.
Fig. 3 is the contact angle of water on properties-correcting agent I-1 modified glass surface.
Fig. 4 is the contact angle of water on properties-correcting agent I-2 modified glass surface.
Fig. 5 is the contact angle of water on properties-correcting agent I-3 modified glass surface.
Fig. 6 is the contact angle of water on properties-correcting agent I-4 modified glass surface.
Fig. 7 is the contact angle of water on properties-correcting agent I-5 modified glass surface.
Embodiment
The embodiment of a kind of glass surface hydrophobic modifier of the present invention and synthetic method thereof is provided below in conjunction with accompanying drawing, 5 embodiments and 1 Application Example are provided.But it is noted that enforcement of the present invention is not limited to following embodiment.
embodiment 1
A synthetic method for glass surface hydrophobic modifier, containing following steps:
(1) component prepares
In 1000mL there-necked flask, add 3.69g(20mmol successively) cyanuric chloride, 11.2g(80mmol) Anhydrous potassium carbonate; add 400mL dioxane under nitrogen protection again; under ice-water bath cooling; drip 20.2g(40mmol again) dioxane (100mL) solution of three-[(2-tert-butoxycarbonyl oxyethyl group)-methyl]-methylamines, above-mentioned raw materials is mixed.
(2) react
The mixing raw material of step (1) is first reacted 1h under 0 DEG C of ice-water bath; Then room temperature reaction 2h; Back flow reaction 20h again.
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction
The basis of step (2) reactant adds 3-aminopropyl three (oxyethyl group) silane 22.5g(100mmol) 100mL dioxane solution, back flow reaction 10h.
(4) remove organic solvent and wash
Decompression removing organic solvent and dioxane and excessive 3-aminopropyl triethoxysilane, then priority water and petroleum ether residuum no longer reduce to weight, obtain the glass surface hydrophobic modifier 20.1g of yellow mucus shape, productive rate is 77%, is numbered properties-correcting agent I-1.
The chemical equation of described synthetic method is:
。
Adopt NMR (Nuclear Magnetic Resonance) spectrum method to detect the glass surface hydrophobic modifier that embodiment 1 is synthesized, detected result is:
1H NMR(CDCl
3, 400MHz, 25℃), δ(ppm): 3.86-3.78(m, 18H), 3.64(t,
J= 6.4Hz, 12H), 3.31(d,
J= 4.8Hz, 2H), 2.45(t,
J= 10.4Hz, 12H), 1.44(s, 56H), 1.23(t,
J= 7.2Hz, 9H), 0.53(t, J=7.0Hz, 2H)。
13C NMR(CDCl
3, 100MHz, 25℃), δ(ppm): 171.9, 165.4, 80.3, 69.6, 67.0, 59.3, 58.4, 36.3, 28.3, 28.1, 23.2, 18.3, 7.8, 0.01。
embodiment 2
A synthetic method for glass surface hydrophobic modifier, containing following steps:
(1) component prepares
Basic with embodiment 1, distinguishing:
Described three-(2-carbalkoxy ethoxymethyl)-methylamines are trimethyl carbinol ester 22.5g.
(2) (with embodiment 1) is reacted.
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction
Basic with embodiment 1, distinguishing:
The basis of step (2) reactant adds 3-aminopropyl trimethoxy silane 17.8g.
(4) remove organic solvent and wash
Basic with embodiment 1, obtain the glass surface hydrophobic modifier 19.2g of yellow mucus shape, productive rate is 76%, is numbered properties-correcting agent I-2.
embodiment 3
A synthetic method for glass surface hydrophobic modifier, containing following steps:
(1) component prepares
Basic with embodiment 1, distinguishing:
Described three-(2-carbalkoxy ethoxymethyl)-methylamines are hexamethylene alcohol ester 23.4g.
(2) (with embodiment 1) is reacted.
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction (with embodiment 1).
(4) remove organic solvent and wash
Basic with embodiment 1, obtain the glass surface hydrophobic modifier 21.5g of yellow mucus shape, productive rate is 73%, is numbered properties-correcting agent I-3.
embodiment 4
A synthetic method for glass surface hydrophobic modifier, containing following steps:
(1) component prepares
Basic with embodiment 1, distinguishing:
Add 600mL dioxane under nitrogen protection;
Described three-(2-carbalkoxy ethoxymethyl)-methylamines are isooctyl alcohol ester 27.0g.
(2) (with embodiment 1) is reacted.
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction (with embodiment 1).
(4) remove organic solvent and wash
Basic with embodiment 1, obtain the glass surface hydrophobic modifier 24.6g of yellow mucus shape, productive rate is 75%, is numbered properties-correcting agent I-4.
embodiment 5
A synthetic method for glass surface hydrophobic modifier, containing following steps:
(1) component prepares
Basic with embodiment 1, distinguishing:
Add 600mL dioxane under nitrogen protection;
Described three-(2-carbalkoxy ethoxymethyl)-methylamines are lauryl alcohol ester 33.5g.
(2) (with embodiment 1) is reacted.
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction (with embodiment 1).
(4) remove organic solvent and wash
Basic with embodiment 1, obtain the glass surface hydrophobic modifier 26.5g of yellow mucus shape, productive rate is 67%, is numbered properties-correcting agent I-5
.
The synthesis of embodiment 1-5 the results are shown in Table 1.
The synthesis table look-up of table 1. embodiment 1 ~ 5 glass surface hydrophobic modifier
。
application Example 1
The application of the glass surface hydrophobic modifier of the present invention's synthesis, comprises the following steps:
(1) first, alternately clean surface of ordinary glass 3 times with dehydrated alcohol and acetone, each scavenging period is 3 minutes.
(2) then, the glass that step (1) is cleaned is placed in the hydrogen peroxide (30%) that volume ratio is 1:3 and cleans 15 minutes with the mixing solutions of the vitriol oil (98%); Use deionized water ultrasonic cleaning again 3 times, then hot blast drying.
(3) glass immersion again step (2) dried up pH value be 6, in the dioxane solution of glass surface hydrophobic modifier numbering I-1 ~ I-5 that the present invention containing 0.1mol/L synthesizes 1 hour.
(4) last, sheet glass step (3) handled well takes out, and uses methylene dichloride, ethanol and washed with de-ionized water glass surface successively, hot blast drying, obtains the glass of surface hydrophobicity modification.
To the test result of the glass of the surface hydrophobicity modification that Application Example 1 obtains be:
The contact angle of the glass surface that the glass surface hydrophobic modifier of synthesizing with invention is modified is 75.5 ~ 95.1
obetween, and contact angle is before modified 21.4
o; The transmittance of 550nm visible light wavelengths before modification after substantially constant, see table 2.
The contact angle on water and modified glass surface and glass transmission rate in table 2. Application Example 1
。
Application Example 1 proves: simple glass is water repellent surface through the surface that glass surface hydrophobic modifier of the present invention is modified and has good glass transmission rate.
Claims (4)
1. a glass surface hydrophobic modifier, is characterized in that, take s-triazine as core, and peripheral end group is six hydrophobic alkyl end groups and a coupling base, and its structural formula is:
In formula:
R
1for the alkyl of 4-12 carbon;
R
2for methyl or ethyl.
2. a synthetic method for glass surface hydrophobic modifier as claimed in claim 1, is characterized in that, containing following steps:
(1) component prepares
Under nitrogen atmosphere, to adding the cyanuric chloride of 1 times of molar weight, three-(2-carbalkoxy ethoxymethyl)-methylamines of 2 times of molar weights, the salt of wormwood of 4 times of molar weights and dioxane in the reactor of reflux as solvent, above-mentioned raw materials is mixed;
(2) react
The mixing raw material of step (1) is first reacted 1h under 0 DEG C of ice-water bath; Then room temperature reaction 2h; Back flow reaction 20h again;
(3) add 3-aminopropyltrialkoxy silanes and continue back flow reaction
The basis of step (2) reactant adds the 3-aminopropyltrialkoxy silanes of 5 times of molar weights, continues back flow reaction 10h;
(4) remove organic solvent and wash
Pressure reducing and steaming organic solvent and dioxane and excessive 3-aminopropyltrialkoxy silanes, priority water and petroleum ether removing impurity again, obtain glass surface hydrophobic modifier---2-(3-organoalkoxysilane Propylamino)-4,6-bis--[three-(2-carbalkoxy ethoxyl methyl)-methylaminos]-[1,3,5]-triazine;
The chemical equation of described synthetic method is:
。
3. synthetic method according to claim 2, is characterized in that, described in step (1) three-(2-carbalkoxy ethoxymethyl)-methylamines are one of trimethyl carbinol ester in C4-C12 alcohol ester, hexamethylene alcohol ester, isooctyl alcohol ester or lauryl alcohol ester.
4. synthetic method according to claim 2, is characterized in that, the 3-aminopropyltrialkoxy silanes described in step (3) is the one in methoxyl group or oxyethyl group.
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|---|---|---|---|
| CN201510246902.8A CN104910203B (en) | 2015-05-13 | 2015-05-13 | A kind of glass surface hydrophobic modifier and its synthetic method |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201510246902.8A CN104910203B (en) | 2015-05-13 | 2015-05-13 | A kind of glass surface hydrophobic modifier and its synthetic method |
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| Publication Number | Publication Date |
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| CN104910203A true CN104910203A (en) | 2015-09-16 |
| CN104910203B CN104910203B (en) | 2018-03-06 |
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143728A (en) * | 2022-10-18 | 2023-05-23 | 智仑超纯环氧树脂(西安)有限公司 | Reactive epoxy hydrophobic modifier and preparation method and application thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1158364A (en) * | 1995-10-26 | 1997-09-03 | 默克专利股份有限公司 | Material for and method of preparing water-repellent coatings on optical substrates |
| US20050106068A1 (en) * | 2003-11-18 | 2005-05-19 | Abdul Malik | Sol-gel dendron separation and extraction capillary column |
| CN102952158A (en) * | 2012-10-26 | 2013-03-06 | 大连理工大学 | Triazine type siloxane surface modifier and preparation method thereof |
-
2015
- 2015-05-13 CN CN201510246902.8A patent/CN104910203B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1158364A (en) * | 1995-10-26 | 1997-09-03 | 默克专利股份有限公司 | Material for and method of preparing water-repellent coatings on optical substrates |
| US20050106068A1 (en) * | 2003-11-18 | 2005-05-19 | Abdul Malik | Sol-gel dendron separation and extraction capillary column |
| CN102952158A (en) * | 2012-10-26 | 2013-03-06 | 大连理工大学 | Triazine type siloxane surface modifier and preparation method thereof |
Non-Patent Citations (2)
| Title |
|---|
| MARCELO CALDERON等，: "Electrochemical Study of a Dendritic Family at the Water/1,2-Dichloroethane Interface", 《LANGMUIR》 * |
| SUBHENDU K. MOHANTY等，: "Photophysical properties of Newkome-type dendrimers in aqueous medium", 《PHOTOCHEM. PHOTOBIOL. SCI.》 * |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN116143728A (en) * | 2022-10-18 | 2023-05-23 | 智仑超纯环氧树脂(西安)有限公司 | Reactive epoxy hydrophobic modifier and preparation method and application thereof |
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| CN104910203B (en) | 2018-03-06 |
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Granted publication date: 20180306 Termination date: 20200513 |