CN116217091B - Application of dihydroxyamino propyl silane coupling agent in glass surface modification - Google Patents
Application of dihydroxyamino propyl silane coupling agent in glass surface modification Download PDFInfo
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- CN116217091B CN116217091B CN202310116727.5A CN202310116727A CN116217091B CN 116217091 B CN116217091 B CN 116217091B CN 202310116727 A CN202310116727 A CN 202310116727A CN 116217091 B CN116217091 B CN 116217091B
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- coupling agent
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- silane coupling
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- 239000011521 glass Substances 0.000 title claims abstract description 113
- 239000006087 Silane Coupling Agent Substances 0.000 title claims abstract description 31
- 230000004048 modification Effects 0.000 title claims abstract description 12
- 238000012986 modification Methods 0.000 title claims abstract description 12
- -1 dihydroxyamino propyl silane Chemical compound 0.000 title abstract description 25
- WFACWTZLXIFJCM-UHFFFAOYSA-N 5-(chloromethyl)-2-hydroxybenzaldehyde Chemical compound OC1=CC=C(CCl)C=C1C=O WFACWTZLXIFJCM-UHFFFAOYSA-N 0.000 claims abstract description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 72
- 239000000243 solution Substances 0.000 claims description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 17
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 14
- 239000007822 coupling agent Substances 0.000 claims description 14
- XABJJJZIQNZSIM-UHFFFAOYSA-N azane;phenol Chemical compound [NH4+].[O-]C1=CC=CC=C1 XABJJJZIQNZSIM-UHFFFAOYSA-N 0.000 claims description 13
- 239000000758 substrate Substances 0.000 claims description 13
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 230000015572 biosynthetic process Effects 0.000 claims description 9
- 238000003786 synthesis reaction Methods 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 8
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 claims description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 6
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 6
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 claims description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 6
- 239000008367 deionised water Substances 0.000 claims description 6
- 229910021641 deionized water Inorganic materials 0.000 claims description 6
- 238000001035 drying Methods 0.000 claims description 6
- 239000000126 substance Substances 0.000 claims description 6
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 claims description 5
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 4
- 241000252506 Characiformes Species 0.000 claims description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 4
- 238000006243 chemical reaction Methods 0.000 claims description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 claims description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 4
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 claims description 4
- 239000000463 material Substances 0.000 claims description 4
- 239000003960 organic solvent Substances 0.000 claims description 4
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 claims description 4
- 238000001291 vacuum drying Methods 0.000 claims description 4
- SJECZPVISLOESU-UHFFFAOYSA-N 3-trimethoxysilylpropan-1-amine Chemical compound CO[Si](OC)(OC)CCCN SJECZPVISLOESU-UHFFFAOYSA-N 0.000 claims description 3
- 238000001816 cooling Methods 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 3
- WYTZZXDRDKSJID-UHFFFAOYSA-N (3-aminopropyl)triethoxysilane Chemical compound CCO[Si](OCC)(OCC)CCCN WYTZZXDRDKSJID-UHFFFAOYSA-N 0.000 claims description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 claims description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 claims description 2
- HXLAEGYMDGUSBD-UHFFFAOYSA-N 3-[diethoxy(methyl)silyl]propan-1-amine Chemical compound CCO[Si](C)(OCC)CCCN HXLAEGYMDGUSBD-UHFFFAOYSA-N 0.000 claims description 2
- ZYAASQNKCWTPKI-UHFFFAOYSA-N 3-[dimethoxy(methyl)silyl]propan-1-amine Chemical compound CO[Si](C)(OC)CCCN ZYAASQNKCWTPKI-UHFFFAOYSA-N 0.000 claims description 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 claims description 2
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 claims description 2
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 claims description 2
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 2
- 238000005406 washing Methods 0.000 claims description 2
- 150000002430 hydrocarbons Chemical group 0.000 claims 1
- 238000006482 condensation reaction Methods 0.000 abstract description 4
- 238000005956 quaternization reaction Methods 0.000 abstract description 3
- 238000002834 transmittance Methods 0.000 abstract description 3
- 239000011159 matrix material Substances 0.000 abstract description 2
- 238000002715 modification method Methods 0.000 abstract 1
- 235000019441 ethanol Nutrition 0.000 description 15
- 238000004140 cleaning Methods 0.000 description 6
- 230000033444 hydroxylation Effects 0.000 description 6
- 238000005805 hydroxylation reaction Methods 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- 238000011049 filling Methods 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- YKPUWZUDDOIDPM-SOFGYWHQSA-N capsaicin Chemical compound COC1=CC(CNC(=O)CCCC\C=C\C(C)C)=CC=C1O YKPUWZUDDOIDPM-SOFGYWHQSA-N 0.000 description 2
- 239000005357 flat glass Substances 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 150000002443 hydroxylamines Chemical class 0.000 description 2
- 150000002500 ions Chemical class 0.000 description 2
- 244000005700 microbiome Species 0.000 description 2
- 239000011259 mixed solution Substances 0.000 description 2
- 125000001453 quaternary ammonium group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- QDHHCQZDFGDHMP-UHFFFAOYSA-N Chloramine Chemical compound ClN QDHHCQZDFGDHMP-UHFFFAOYSA-N 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 229920002125 Sokalan® Polymers 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 1
- 239000003242 anti bacterial agent Substances 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 229960002504 capsaicin Drugs 0.000 description 1
- 235000017663 capsaicin Nutrition 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000001514 detection method Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 230000036571 hydration Effects 0.000 description 1
- 238000006703 hydration reaction Methods 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 229920002401 polyacrylamide Polymers 0.000 description 1
- 239000004584 polyacrylic acid Substances 0.000 description 1
- 229920001223 polyethylene glycol Polymers 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 239000005368 silicate glass Substances 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
Classifications
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- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C23/00—Other surface treatment of glass not in the form of fibres or filaments
- C03C23/0095—Solution impregnating; Solution doping; Molecular stuffing, e.g. of porous glass
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/70—Properties of coatings
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2218/00—Methods for coating glass
- C03C2218/30—Aspects of methods for coating glass not covered above
- C03C2218/31—Pre-treatment
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Surface Treatment Of Glass (AREA)
Abstract
The invention provides an application of a dihydroxyamino propyl silane coupling agent in glass surface modification, in particular to a modification method of grafting phenolammonium zwitterions on the glass surface, which is realized by condensation reaction of the dihydroxyamino propyl silane coupling agent and the hydroxylated glass surface and then quaternization reaction of the dihydroxyamino propyl silane coupling agent and 5-chloromethylsalicylaldehyde. The functionalized layers bonded with quaternary ammonium cations and phenolammonium zwitterions on the surfaces of the glass are monomolecular layers, and are distributed in a dot matrix manner, so that the uniformity is high, and the modified glass is high in light transmittance and super-hydrophilic.
Description
Technical Field
The invention relates to an application of a dihydroxyamino propyl silane coupling agent in glass surface modification, which is realized by condensation reaction of the dihydroxyamino propyl silane coupling agent and hydroxyl groups on the glass surface and then quaternization reaction of the dihydroxyamino propyl silane coupling agent and 5-chloromethyl salicylaldehyde, and belongs to the technical field of glass surfaces.
Technical Field
Silicate glass is an isotropic amorphous inorganic material having high light transmittance, high hardness, high pressure resistance, wear resistance, corrosion resistance, and has been widely manufactured into glass optical windows of domestic glass products, vehicle windshields, medical glass products, glass curtain walls, glass greenhouses, photovoltaic glass, underwater equipment, etc. in view of its good workability. In particular, it has been clarified that the high hydrophilicity and antibacterial function of the optical window glass of the underwater equipment are necessary conditions for securing the effective use thereof, and for this purpose many CN201210442595.7、CN201410321560.7、CN201410145198.2、CN201410551397.3、CN201110155872.1、CN202210463398.7 and the like indicate that new chemical active centers can be established by condensation reaction of silane coupling agents carrying-c=c, -NH 2, -SH, -NCO or epoxy groups on the surface of the hydroxylated glass, graft copolymerization can be performed according to these chemical active centers, polyethylene glycol, polyacrylic acid, polyacrylamide, quaternary ammonium carboxylic acid inner salt, quaternary ammonium phosphoric acid inner salt or quaternary ammonium sulfonic acid inner salt, and the like are linked, and these hydrophilic substances form hydration layers on the surface of the glass, which can isolate and prevent suspended substances in water or microorganisms from contacting or adhering on the surface of the glass, or introduce some antibacterial agents such as capsaicin, chloramine, quaternary ammonium salt, and the like on the surface of the glass, kill or inhibit the proliferation and growth of microorganisms on the surface of the glass, thereby achieving self-cleaning of the optical window glass. Therefore, the realization of super-hydrophilic modification of the glass surface by a simple method is of great importance.
Disclosure of Invention
The invention provides an application of a dihydroxyamino propyl silane coupling agent in glass surface modification, which is realized by condensation reaction of the dihydroxyamino propyl silane coupling agent and hydroxyl groups on the glass surface and then quaternization reaction of the dihydroxyamino propyl silane coupling agent and 5-chloromethyl salicylaldehyde, wherein the specific technical scheme is as shown in the following reaction formula:
Wherein R in the formula is selected from H or methyl.
The specific scheme for realizing the application of the dihydroxyamino propyl silane coupling agent in glass surface modification is as follows:
and firstly, filling an ethanol aqueous solution of a dihydroxyaminopropyl silane coupling agent on the surface of the hydroxylated glass sheet, placing the hydroxylated glass sheet in a 30-130 ℃ oven, taking out and cooling the hydroxylated glass sheet after the time is controlled to be 0.5-20 hours, cleaning the glass sheet by using ethanol, and drying the glass sheet to obtain the surface hydroxylamines glass sheet.
The hydroxylation glass sheet is prepared by the following steps of filling a piranha solution prepared by concentrated sulfuric acid with the mass percentage concentration of 98% and hydrogen peroxide with the mass percentage concentration of 30% according to the volume ratio of 9:1-7:3 on the surface of a cleaned and dried glass substrate, controlling the temperature to be 20-120 ℃ for 0.5-50 hours, taking out the glass substrate, cleaning the surface of the glass sheet by deionized water, and then vacuum drying at 60-90 ℃ to obtain the surface hydroxylation glass sheet.
Wherein the use amount of the piranha solution is 2-200% of the mass of the glass substrate.
The mass ratio of the dihydroxyaminopropyl silane coupling agent to ethanol in the dihydroxyaminopropyl silane coupling agent ethanol aqueous solution is 2-8:85-95:3-7, and the dosage of the dihydroxyaminopropyl silane coupling agent ethanol aqueous solution is 5-500% of the mass of the hydroxylated glass sheet;
The dihydroxyaminopropyl silane coupling agent disclosed by the invention has a chemical structure shown in a general formula (1):
Wherein R 1、R2 and R 3 in the general formula (1) are respectively selected from substituted or substituted C 1～C18 alkyl, and R is selected from H or methyl.
The preparation method comprises the steps of adding ethanol and an aminosilane coupling agent into a synthesis reactor, controlling the temperature of the materials in the synthesis reactor to be 10-60 ℃, slowly adding the hydroxyethyl acrylate or the hydroxyethyl methacrylate into the synthesis reactor under stirring, continuing to react for 2-6 hours after the addition, and adding ethanol and water into the ethanol solution of the dihydroxyaminopropyl silane coupling agent, so that the mass ratio of ethanol to water in the ethanol solution of the dihydroxyaminopropyl silane coupling agent is 2-8:85-95:3-7 for later use.
The aminosilane coupling agent is one or more than two of 3-aminopropyl trimethoxy silane, 3-aminopropyl triethoxy silane, N- (2-amino ethyl) -3-aminopropyl trimethoxy silane, N- (2-amino ethyl) -3-aminopropyl triethoxy silane, 3-aminopropyl dimethoxy methyl silane and 3-aminopropyl diethoxy methyl silane, and the dosage mole ratio of the aminosilane coupling agent to hydroxyethyl acrylate or hydroxyethyl methacrylate is 2.0-2.2.
And secondly, adding a 5-chloromethylsalicylaldehyde solution on the surface of the hydroxylamines glass sheet obtained in the step one, placing the glass sheet into a reactor at a temperature of between 0 and 60 ℃ for controlling the reaction time to be between 0.5 and 50 hours, taking out the glass sheet, cleaning the glass sheet by using acetone to remove unreacted 5-chloromethylsalicylaldehyde on the glass sheet, eluting the glass sheet by using deionized water to be neutral, and drying the glass sheet to obtain the surface grafted ammonium phenolate amphoteric ion glass sheet.
Wherein the mass ratio of the 5-chloromethyl salicylaldehyde to the organic solvent in the 5-chloromethyl salicylaldehyde solution is 0.01-0.5:1, and the dosage of the 5-chloromethyl salicylaldehyde solution is 2-200% of the mass of the hydroxylated glass sheet.
The organic solvent is one or more of acetone, butanone, cyclohexanone, methyl acetate, ethyl acetate, chloroform, 1, 2-dichloroethane, carbon tetrachloride, tetrahydrofuran, 1, 4-dioxane, decalin, toluene, chlorobenzene, dimethyl sulfoxide or N, N-dimethylacetamide.
The method for grafting the ammonium phenolate amphoteric ion on the glass surface has the advantages of simple technology, easiness in implementation, wide sources of raw materials, low price, high reaction efficiency in each preparation step and no mutual influence between the preparation process and the preparation process.
The functionalized layers grafted with the ammonium phenolate zwitterions on the surfaces of the glass are all monomolecular layers, and are distributed in a dot matrix mode and high in uniformity, so that the light transmittance of the modified glass is not influenced by the ammonium phenolate zwitterions grafted on the surfaces of the modified glass.
Detailed Description
For a further understanding of the present invention, reference will now be made in detail to the present examples, which are included in the accompanying drawings. Therefore, the use of the dihydroxyaminopropyl silane coupling agent not listed in the examples in the modification of glass surfaces should not be considered as limiting the scope of protection of the present invention.
Example 1 preparation of ammonium phenolate zwitterionic glass sheet (1-a)
Preparing a hydroxylated glass sheet, namely cleaning and drying a glass substrate (glass slide, jiangsu Feilong glass plastic Co., ltd.) of 7.6-2.5-0.15 cm, preparing 5 g of mixed solution of concentrated sulfuric acid and hydrogen peroxide according to a volume ratio of 7:3, adding the mixed solution on the glass sheet, treating the glass sheet at 60-70 ℃ for 2 hours, leaching the glass sheet to be neutral by deionized water, and vacuum-drying the glass sheet at 60 ℃ to obtain the surface hydroxylated glass sheet (1-a).
3.60 G of 3-aminopropyl trimethoxy silane is added into a synthesis reactor, the temperature of the materials in the synthesis reactor is controlled to be 20-30 ℃, 2.66 g of hydroxyethyl methacrylate is slowly dripped into the synthesis reactor under stirring, after the material feeding is finished, the heat preservation reaction is continued for 4 hours, 20 g of aqueous ethanol solution with the mass percent concentration of 5% is added, and the aqueous ethanol solution of the dihydroxyamino propyl silane coupling agent with the formula (1-a) is prepared for standby.
And firstly, filling the ethanol aqueous solution of the dihydroxyaminopropyl silane coupling agent shown in the formula (1-a) on the surface of the hydroxylated glass sheet (1-a), putting the hydroxylated glass sheet into an oven at 80-90 ℃, taking out the hydroxylated glass sheet after 2 hours, cooling the hydroxylated glass sheet, washing the glass sheet with ethanol, and drying the glass sheet to obtain the surface hydroxylation glass sheet (1-a).
And step two, placing the surface hydroxylamine glass sheet (1-a) obtained in the step one into a reactor, controlling the temperature to be 5-10 ℃, slowly filling 5g of acetone solution of 5-chloromethyl salicylaldehyde with the mass percentage concentration of 40% on the surface of the glass sheet, taking out the glass sheet after 2 hours, cleaning the glass sheet by using acetone to remove unreacted 5-chloromethyl salicylaldehyde, sequentially eluting the glass surface by using ethanol and deionized water, and vacuum drying to obtain the surface grafted ammonium phenolate zwitterionic glass sheet (1-a).
After the glass substrate, the hydroxylation glass sheet (1-a) and the phenolammonium zwitterionic glass sheet (1-a) are respectively placed in absolute ethyl alcohol and soaked for 0.5 hour, an infrared spectrum test is carried out, an absorption peak with medium intensity is shown at 1692nm, which is the typical characteristic absorption peak of aldehyde carbonyl C=O, an absorption peak with medium intensity is shown at 1734nm, which is the typical characteristic absorption peak of ester carbonyl C=O, and the glass substrate and the hydroxylation glass sheet (1-a) have no absorption peak near 1700nm, thereby confirming that the actual preparation process of the surface grafted phenolammonium zwitterionic glass sheet is completely consistent with the theoretical design scheme, and indicating that the surface of the glass sheet is successfully grafted with phenolammonium zwitterionic.
Example 2 preparation of ammonium phenolate zwitterionic glass sheet (1-b)
According to the method and the operation procedure of example 1, hydroxyethyl methacrylate in the stock of the dihydroxyaminopropyl silane coupling agent in example 1 was changed to hydroxyethyl acrylate, and a glass sheet (1-b) with surface grafted with ammonium phenolate zwitterion was produced.
Example 3 characterization of surface-grafted ammonium phenolate zwitterionic glass sheets
According to GB/T24368-2009 glass surface hydrophobic contaminant detection contact angle measurement method, the pure water contact angles of the glass substrates, the hydroxylated glass sheets and the surface grafted ammonium phenolate zwitterionic glass sheets of examples 1-2 are measured, and are shown in Table 1.
TABLE 1 pure water contact angle of glass sheets
| Sample numbering | 1-a | 1-b | Glass substrate | Hydroxylated glass sheet |
| Water contact angle theta | 0 | 0 | 53.2 | 41.4 |
The test results in table 1 show that the glass substrate has a reduced water contact angle after hydroxylation treatment, and the water contact angle is reduced to 0 after the surface grafting of the ammonium phenolate zwitterion, which shows that the surface of the glass sheet has super-hydrophilicity, and also shows that the surface of the glass sheet has been successfully grafted with the ammonium phenolate zwitterion.
Claims (4)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310116727.5A CN116217091B (en) | 2023-02-15 | 2023-02-15 | Application of dihydroxyamino propyl silane coupling agent in glass surface modification |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202310116727.5A CN116217091B (en) | 2023-02-15 | 2023-02-15 | Application of dihydroxyamino propyl silane coupling agent in glass surface modification |
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| Publication Number | Publication Date |
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| CN116217091A CN116217091A (en) | 2023-06-06 |
| CN116217091B true CN116217091B (en) | 2025-03-14 |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN117049794A (en) * | 2023-08-16 | 2023-11-14 | 江苏海洋大学 | Application of functional silane coupling agent in surface modification of bioactive glass |
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| JPH0959041A (en) * | 1995-06-14 | 1997-03-04 | Toto Ltd | Anticlouding coating composition containing photocatalyst |
| US6099852A (en) * | 1998-09-23 | 2000-08-08 | Johnson & Johnson Vision Products, Inc. | Wettable silicone-based lenses |
| KR101864757B1 (en) * | 2016-11-11 | 2018-06-05 | 한국생산기술연구원 | Insulation coating composition for plating rack and manufacturing method thereof |
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| CN117049794A (en) * | 2023-08-16 | 2023-11-14 | 江苏海洋大学 | Application of functional silane coupling agent in surface modification of bioactive glass |
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