CN111153926A - Organic silicon compound for ultraviolet-curing super-hydrophobic coating and preparation method thereof - Google Patents
Organic silicon compound for ultraviolet-curing super-hydrophobic coating and preparation method thereof Download PDFInfo
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- CN111153926A CN111153926A CN202010036176.8A CN202010036176A CN111153926A CN 111153926 A CN111153926 A CN 111153926A CN 202010036176 A CN202010036176 A CN 202010036176A CN 111153926 A CN111153926 A CN 111153926A
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- Prior art keywords
- organic silicon
- silicon compound
- ultraviolet
- formula
- hydrophobic coating
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- 239000011248 coating agent Substances 0.000 title claims abstract description 24
- 238000000576 coating method Methods 0.000 title claims abstract description 24
- 150000003377 silicon compounds Chemical class 0.000 title claims abstract description 23
- 230000003075 superhydrophobic effect Effects 0.000 title claims abstract description 16
- 238000002360 preparation method Methods 0.000 title abstract description 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 claims abstract description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 7
- 239000003054 catalyst Substances 0.000 claims abstract description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 10
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 6
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 6
- 238000010438 heat treatment Methods 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 239000003377 acid catalyst Substances 0.000 claims description 2
- 230000002378 acidificating effect Effects 0.000 claims description 2
- 238000000034 method Methods 0.000 claims 4
- 150000003961 organosilicon compounds Chemical class 0.000 claims 2
- 239000002994 raw material Substances 0.000 claims 1
- 239000011521 glass Substances 0.000 abstract description 12
- 239000000758 substrate Substances 0.000 abstract description 6
- 125000004185 ester group Chemical group 0.000 abstract description 3
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract description 3
- 229920002554 vinyl polymer Polymers 0.000 abstract description 3
- 239000002904 solvent Substances 0.000 abstract description 2
- 238000001723 curing Methods 0.000 description 16
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000003889 chemical engineering Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 230000005611 electricity Effects 0.000 description 1
- 238000004134 energy conservation Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- 238000009776 industrial production Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 239000008204 material by function Substances 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 238000001029 thermal curing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D143/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium, or a metal; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
Abstract
The invention discloses an organic silicon compound for an ultraviolet curing super-hydrophobic coating, which is characterized by having a structure shown as a formula (1):
Description
Technical Field
The invention belongs to the field of synthesis of novel organic silicon functional materials, and particularly relates to an organic silicon compound for an ultraviolet-cured super-hydrophobic coating and a preparation method thereof.
Background
The organic silicon compound has the basic properties of small surface tension, low surface energy and the like due to the unique structure of the organic silicon compound, and has the excellent characteristics of high and low temperature resistance, electrical insulation, chemical stability resistance, weather resistance, corrosion resistance, hydrophobicity and the like, so that the organic silicon compound has wide application in the industries of aerospace, electronics and electricity, construction, transportation, chemical engineering, textile, food, light industry, medical treatment and the like. The characteristics of low surface tension and low surface energy are the important reasons for the excellent characteristics of the coating in hydrophobic, defoaming and coating applications.
At present, the ultraviolet curing technology has the advantages of high efficiency, energy conservation, environmental protection, good adhesion with base materials, excellent coating performance and the like, thereby being particularly suitable for industrial production. The traditional organic silicon coating is basically in a thermal curing mode, and the curing mode is high in energy consumption and low in efficiency. If the ultraviolet curing technology is combined with the organic silicon compound, the advantages of the ultraviolet curing technology and the organic silicon compound can be more remarkable, and the ultraviolet curing organic silicon coating with various excellent performances such as durability, weather resistance, super hydrophobicity and the like can be obtained.
Disclosure of Invention
The invention aims to provide an organic silicon compound for an ultraviolet light curing super-hydrophobic coating and a preparation method thereof.
In order to solve the technical problems, the invention adopts the following technical scheme:
an organic silicon compound for an ultraviolet light curing super-hydrophobic coating is characterized by having a structure shown as a formula (1):
the organic silicon compound contains vinyl, phenyl and ester groups, has excellent affinity with a glass substrate, can be cured to form a coating under the action of a photoinitiator and ultraviolet light, and has a good super-hydrophobic effect.
A preparation method of an organic silicon compound for an ultraviolet light curing super-hydrophobic coating is characterized by comprising the following steps: the formula (1) is formed by removing methanol through the reaction of trimethoxy phenyl silane and 2-hydroxyethyl acrylate under the action of a catalyst. The specific reaction formula is as follows:
preferably, the preparation method of the organic silicon compound for the ultraviolet-curing super-hydrophobic coating comprises the following steps:
(a) adding trimethoxy phenyl silane and an acid catalyst into a reactor protected by nitrogen and anhydrous and stirring;
(b) gradually heating to 80-120 deg.C, and simultaneously adding 2-hydroxyethyl acrylate;
(c) after the dripping is finished, the mixture is kept at a constant temperature and stirred for reaction for 4 to 8 hours, and the organic silicon compound with the structure of the formula (1) is prepared.
Preferably, the molar ratio of trimethoxyphenylsilane to 2-hydroxyethyl acrylate is 1: 3.
A preferred acidic catalyst is dibutyltin dilaurate, which is used in an amount of 0.5 to 2%, preferably 1.2%, based on the total mass of the starting materials.
Due to the adoption of the technical scheme, the invention has the following beneficial effects:
the organic silicon compound contains vinyl, phenyl and ester groups, has excellent affinity with a glass substrate, can be cured to form a coating under the action of a photoinitiator and ultraviolet light, and has a good super-hydrophobic effect. Compared with the prior art, the organic silicon compound has the advantages of simple and easy operation in the preparation process, no need of solvent, special structure, lower surface tension and great application value.
Detailed Description
Example 1
Adding 19.8290g of trimethoxy phenyl silane (0.1mol) and 0.2733g of dibutyltin dilaurate into a four-neck flask which is protected by nitrogen, gradually heating to 80 ℃ while stirring, simultaneously dropwise adding 34.8360g of 2-hydroxyethyl acrylate (0.3mol), keeping constant temperature for reaction for 4 hours after dropwise adding, and cooling to obtain the target product. 3600-3000cm by infrared spectrum analysis-1The OH stretching vibration absorption peak in the acrylic acid-2-hydroxyethyl ester in the frequency range disappears, which indicates that the acrylic acid-2-hydroxyethyl ester is completely reacted, and the target product with the structure shown in the formula (1) is obtained.
The target product and a commercially available BASF Irgacure photoinitiator are fully and uniformly mixed according to the ratio of 100:5, coated on a glass substrate and placed in an ultraviolet curing machine for ultraviolet curing. The glass sheet was then removed and the water contact angle of the glass coating was tested to 145 ° according to national standard GB/T26490-2011.
Example 2
Adding 19.8290g of trimethoxy phenyl silane (0.1mol) and 0.6560g of dibutyltin dilaurate into a four-neck flask which is protected by nitrogen, gradually heating to 120 ℃ while stirring, simultaneously dropwise adding 34.8360g of 2-hydroxyethyl acrylate (0.3mol), keeping constant temperature for reacting for 6 hours after dropwise adding, and cooling to obtain the target product. 3600-3000cm by infrared spectrum analysis-1The OH stretching vibration absorption peak in the acrylic acid-2-hydroxyethyl ester in the frequency range disappears, which indicates that the acrylic acid-2-hydroxyethyl ester is completely reacted, and the target product with the structure shown in the formula (1) is obtained.
The target product and a commercially available BASF Irgacure photoinitiator are fully and uniformly mixed according to the ratio of 100:5, coated on a glass substrate and placed in an ultraviolet curing machine for ultraviolet curing. The glass sheet was then removed and the water contact angle of the glass coating was tested to be 148 ° according to national standard GB/T26490-2011.
Example 3
Adding 19.8290g of trimethoxy phenyl silane (0.1mol) and 1.0933g of dibutyltin dilaurate into a four-neck flask which is protected by nitrogen, gradually heating to 100 ℃ while stirring, simultaneously dropwise adding 34.8360g of 2-hydroxyethyl acrylate (0.3mol), keeping constant temperature for reacting for 8 hours after dropwise adding, and cooling to obtain the target product. 3600-3000cm by infrared spectrum analysis-1The OH stretching vibration absorption peak in the acrylic acid-2-hydroxyethyl ester in the frequency range disappears, which indicates that the acrylic acid-2-hydroxyethyl ester is completely reacted, and the target product with the structure shown in the formula (1) is obtained.
The target product and a commercially available BASF Irgacure photoinitiator are fully and uniformly mixed according to the ratio of 100:5, coated on a glass substrate and placed in an ultraviolet curing machine for ultraviolet curing. The glass sheet was then removed and the water contact angle of the glass coating was tested to 147 ° according to the national standard GB/T26490-2011.
The above is only a specific embodiment of the present invention, but the technical features of the present invention are not limited thereto. Any simple changes, equivalent substitutions or modifications made on the basis of the present invention to solve the same technical problems and achieve the same technical effects are all covered in the protection scope of the present invention.
Claims (5)
1. An organic silicon compound for an ultraviolet light curing super-hydrophobic coating is characterized by having a structure shown as a formula (1):
2. a method for preparing the organic silicon compound for the ultraviolet-curing super-hydrophobic coating according to claim 1, which is characterized in that: the formula (1) is formed by removing methanol through the reaction of trimethoxy phenyl silane and 2-hydroxyethyl acrylate under the action of a catalyst.
3. The method for preparing the organic silicon compound for the ultraviolet-curing super-hydrophobic coating according to claim 2, characterized by comprising the following steps:
(a) adding the trimethoxy phenyl silane and the acid catalyst into a reactor protected by nitrogen and anhydrous and stirring;
(b) gradually heating to 80-120 ℃, and simultaneously dropwise adding the acrylic acid-2-hydroxyethyl ester;
(c) keeping constant temperature and stirring for reaction for 4-8 hours after the dropwise addition is finished, and obtaining the organic silicon compound with the structure of the formula (1).
4. The method for preparing the organosilicon compound for the UV-curable superhydrophobic coating according to claim 2, wherein: the molar ratio of the trimethoxyphenylsilane to the 2-hydroxyethyl acrylate was 1: 3.
5. The method for preparing the organosilicon compound for the UV-curable superhydrophobic coating according to claim 2, wherein: the acidic catalyst is dibutyltin dilaurate, and the using amount of the dibutyltin dilaurate is 0.5-2% of the total mass of the raw materials.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010036176.8A CN111153926A (en) | 2020-01-14 | 2020-01-14 | Organic silicon compound for ultraviolet-curing super-hydrophobic coating and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202010036176.8A CN111153926A (en) | 2020-01-14 | 2020-01-14 | Organic silicon compound for ultraviolet-curing super-hydrophobic coating and preparation method thereof |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN111153926A true CN111153926A (en) | 2020-05-15 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202010036176.8A Pending CN111153926A (en) | 2020-01-14 | 2020-01-14 | Organic silicon compound for ultraviolet-curing super-hydrophobic coating and preparation method thereof |
Country Status (1)
| Country | Link |
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| CN (1) | CN111153926A (en) |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85106072A (en) * | 1984-06-08 | 1987-01-07 | 威景铁有限公司 | Covering material |
| CN109311917A (en) * | 2016-06-10 | 2019-02-05 | 莫门蒂夫性能材料股份有限公司 | The preparation method of alkoxy silane |
-
2020
- 2020-01-14 CN CN202010036176.8A patent/CN111153926A/en active Pending
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN85106072A (en) * | 1984-06-08 | 1987-01-07 | 威景铁有限公司 | Covering material |
| CN109311917A (en) * | 2016-06-10 | 2019-02-05 | 莫门蒂夫性能材料股份有限公司 | The preparation method of alkoxy silane |
Non-Patent Citations (1)
| Title |
|---|
| XI-E CHENG等，: "UV-curing behavior and properties of tri/di(acryloyloxyethyloxy) phenyl silane used for flame-retardant coatings", 《PROGRESS IN ORGANIC COATINGS》 * |
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Application publication date: 20200515 |
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