CN110903484B - Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same - Google Patents
Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same Download PDFInfo
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- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/60—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which all the silicon atoms are connected by linkages other than oxygen atoms
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- 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/16—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers in which all the silicon atoms are connected by linkages other than oxygen atoms
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
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Abstract
The invention relates to the technical field of novel functional coating materials, and discloses organic silicon modified organic polysilazane and a high-hardness easy-to-clean coating prepared from the same. Based on the concept of human health and environmental friendliness, under the condition of completely abandoning the use of fluoride, the organic polysilazane modified by organic silicon and having excellent anchoring effect and physical and mechanical properties is obtained by modifying the organic polysilazane containing double bonds by using a silane coupling agent with mercapto groups by adopting a click chemistry method; organic polysilazane modified by organic silicon is matched with other organic silane coupling agents and other substances, so that a coating with high hardness and easy cleaning can be obtained at low solid content (10-20 percent), and the production cost can be greatly saved. The method has the advantages of short reaction process time, mild and controllable reaction conditions, simple post-treatment, high yield, simple and stable preparation process, low cost of required equipment, strong operability, easy mass production and good industrial application prospect.
Description
Technical Field
The invention relates to the technical field of novel functional coating materials, in particular to organic silicon modified organic polysilazane and a high-hardness easy-to-clean coating prepared from the same.
Background
With the continuous progress of technology, more and more high performance coatings are beginning to move to people's lives, especially functional coatings, and in recent years, the construction and application of low surface energy surfaces have become one of the most important research directions in the field of functional surfaces. However, one has to face a long standing problem in the construction of low surface energy functional surfaces: researches show that long-chain fluoride with better effect has biological accumulation and persistence and potential harm to the environment and human health, and the fluoride is expensive, so the practical application is greatly limited; however, other substances used at present have poor adhesion with a base material due to low surface energy, so that the performances of surface stability, durability and the like are difficult to meet the long-term practical application requirements.
Polysilazanes have been prepared by stock and somieski research groups since the 20 th century, and this compound has been almost a century of development and application studies in the latter. Polysilazanes have been used mainly for Si3N4Or a Si-C-N ceramic precursor, most of the work is focused on developing the application of the ceramic material by utilizing the characteristic that the ceramic material is formed by high-temperature pyrolysis and conversion of the ceramic material, and the application is expanded to the fields of coatings, adhesives, ceramic matrix composite materials, ceramic films, micro-electro-mechanical systems (MEMS), porous ceramics and the like at present, but the existing research shows that polysilazane has higher required concentration when being used for coatings and treating ceramic and metal surfaces, and the mass fraction of the polysilazane is generally required to be 20-60% so as to cover the larger defects of the substrate surface and achieve the expected performance requirements.
Disclosure of Invention
The invention utilizes the excellent anchoring effect and physical and mechanical properties of the organic polysilazane to be matched with other substances such as organosilane coupling agents and the like to prepare the high-hardness easy-to-clean coating, constructs the environment-friendly fluorine-free super-hydrophobic coating, simultaneously solves the problem of poor adhesion between the substances with low surface energy and the base material for a long time, improves the stability and durability of the coating and the surface, enhances the hardness of the coating and the like
The invention aims to overcome the defects of the prior art, provide an organic silicon modified organic polysilazane with excellent anchoring effect and physical and mechanical properties, and provide an environment-friendly fluorine-free super-hydrophobic high-hardness easy-to-clean coating.
The purpose of the invention is realized by the following technical scheme:
providing an organosilicon modified organopolysilazane obtained by the steps of:
s1, premixing: firstly, dissolving organic polysilazane containing double bonds in a solvent system, then adding a coupling agent containing mercaptosilane, fully mixing, finally adding an initiator, and dissolving and mixing to obtain a mixed solution I;
s2, reaction: reacting the mixed solution I obtained in the step S1 under the conditions of stirring and ultraviolet light irradiation to obtain a mixed solution II;
s3, impurity removal: carrying out reduced pressure distillation on the mixed solution II obtained in the step S2 to obtain the organic silicon modified organic polysilazane;
wherein, the steps S1 to S3 are all performed in an oxygen-free environment.
The general structural formula of the organic polysilazane is
Wherein R is1、R2、R3Some or all of the groups are organic groups; since the electronegativity of Si and N atoms constituting the Si-N bond of the polysilazane macromolecular main chain is different by 1.2, and the electronegativity difference is between the Si-C bond and the Si-O bond, about 30% of the characteristic bonds of the Si-N bond with ionic bonds have a characteristic bond energy of about 355KJ/mol, so that the Si-N bond can be easily converted into other types of new bonds and can easily react with water, polar compounds or oxygen. The organic polysilazane has active chemical properties, and Si-H, Si-N and N-H bonds rich in the molecular structure of the organic polysilazane are easy to react with other substances. Both Si-H and N-H bonds can generate dehydrogenation coupling reaction, and the Si-N bond can generate water/alcoholysis reaction with hydroxyl-containing compounds such as water, alcohol, phenol, silanol and the like, and can also generate reaction with acid, boron or phosphorus halide and the like. In addition, polysilazanes can also participate in important reactions such as hydrosilylation transamination and dehydrocoupling reactions. Due to the unique structure of the material, the material has excellent anchoring performance on the surfaces of most substrate glass, metal materials and the like, Si-H, N-H bonds rich in molecular structures can react with the substrate, so that macromolecules are anchored on the surface of the substrate in a covalent bond mode, and the effect and the efficiency are high. The invention uses polysilazanes with special reaction propertiesThe click chemistry method adopts a series of hydrosulphonyl silane coupling agents to modify organic polysilazane containing double bonds to obtain organic polysilazane compounds modified by organic silicon with different structures.
Preferably, the double bond-containing organic polysilazane of step S1 is a vinyl group-containing organic polysilazane. More preferably, the vinyl group-containing organic polysilazane of step S1 is: one or more of monovinyl-terminated organic polysilazane, divinyl-terminated organic polysilazane, and silicone polysilazane having a vinyl group in a side chain or a cyclic vinyl group.
Preferably, the mercaptosilane coupling agent in step S2 is one or more of mercaptopropyltriethoxysilane, γ -mercaptopropyltrimethoxysilane, γ -mercaptopropylmethyldiethoxysilane, γ -mercaptopropylmethyldimethoxysilane, γ -mercaptopropylisopropoxysilane, and α -mercaptomethyltriethoxysilane.
Preferably, the solvent system of step S1: one or more of isopropanol, ethanol, ethyl acetate, n-butyl ether, propylene glycol monomethyl ether, toluene, xylene, chloroform, and xylene.
Preferably, in the step S2, the reaction is performed at room temperature, the wavelength of the ultraviolet light is 350-370nm, and the irradiation time is 20-40 min.
The invention also provides a high-hardness easy-cleaning coating prepared by the following steps: firstly, adding the obtained organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and a film-forming auxiliary agent, uniformly mixing, then diluting with a diluting solvent to obtain a coating mixed solution III, finally uniformly spraying the obtained coating mixed solution III onto a coating carrier by using a spray gun, and curing to obtain the high-hardness easy-to-clean coating.
According to the invention, the high-hardness easy-to-clean coating is prepared by utilizing the excellent anchoring effect and physical and mechanical properties of organic polysilazane and matching with other materials such as organic silane coupling agents, the environment-friendly fluorine-free super-hydrophobic coating surface is constructed, the problem of poor adhesion between a low-surface-energy material and a base material for a long time is solved, the stability and durability of the coating and the surface are improved, the hardness of the coating is enhanced, and the like.
Preferably, the coalescing agent is dibutyltin laurate. In order to form a complete and compact film material on the whole coating, a reactive group capable of chemically bonding with other organosilane coupling agents needs to be introduced into the molecular chain of the organic polysilazane, so that the coating with good compactness and good anchoring effect with the substrate can be formed.
Preferably, the solid content of the coating mixed solution III is 10% -20%, and the coating carrier is one of glass, metal or wood. The material composed of the coating liquid has higher reactivity, and the surfaces of glass, metal and wood contain groups capable of being combined with the material composed of the coating liquid, so that a compact and strong-binding-force coating can be easily obtained.
Preferably, the thickness of the high hardness easy-to-clean coating obtained by curing is 80-120 μm.
Based on the concept of human health and environmental friendliness, under the condition of completely abandoning the use of fluoride, the organic polysilazane modified by organic silicon and having excellent anchoring effect and physical and mechanical properties is obtained by modifying the organic polysilazane containing double bonds by using a silane coupling agent with mercapto groups by adopting a click chemistry method; the organic polysilazane modified by the organic silicon is matched with other substances such as organic silane coupling agents and the like, and because the organic polysilazane has excellent performance, the high-quality fraction (20% -60%) of the organic polysilazane is not needed, and a coating with high hardness and easy cleaning can be obtained at low solid content (10% -20%), so that the production cost can be greatly saved. The method has the advantages of short reaction process time, mild and controllable reaction conditions, simple post-treatment, high yield, simple and stable preparation process, low cost of required equipment, strong operability, easy mass production and good industrial application prospect.
Drawings
FIG. 1 is a schematic diagram of the reaction for synthesizing organosilicon-modified organopolysilazane described in example 1.
DETAILED DESCRIPTION OF EMBODIMENT (S) OF INVENTION
The invention is further illustrated by the following specific examples. The starting materials and the methods employed in the examples of the present invention are those conventionally available in the art and those conventionally used, and the equipment used is equipment conventional in the art, unless otherwise specified.
Example 1
1. Preparation of organic silicon modified organic polysilazane
S1, premixing: firstly, adding 5g of mercaptopropyltriethoxysilane and 5.36g of trivinyltrimethylcyclotrisilazane into chloroform, fully mixing and dissolving, and finally dissolving and mixing 0.536g of 2, 2-dimethoxy-2-phenylacetophenone (DMPA) to obtain a mixed solution I;
s2, reaction: stirring the mixed solution I obtained in the step S1 at room temperature, and irradiating the mixed solution I with ultraviolet light with the wavelength of 365nm for 30min for reaction, wherein the reaction schematic diagram is shown in figure 1, so as to obtain a mixed solution II;
s3, impurity removal: distilling the mixed solution II obtained in the step S2 under reduced pressure to remove the solvent and unreacted small molecular monomers to obtain organic silicon modified organic polysilazane; wherein, the steps S1 to S3 are all performed under the protection of nitrogen.
2. Preparation of high-hardness easy-to-clean coating
According to the component ratio in the table 1, adding organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and a film forming additive, uniformly mixing, diluting with a diluting solvent to obtain a coating mixed solution III, uniformly spraying the obtained coating mixed solution III onto a glass sheet subjected to pretreatment (the specific substrate treatment method comprises the steps of cleaning the glass sheet for several times by using a cleaning agent to remove oil stains on the surface of the glass sheet, sequentially ultrasonically cleaning the glass sheet for 15min by using acetone, absolute ethyl alcohol and deionized water, placing the cleaned glass sheet on a vacuum drying oven for drying, standing for 7 days in a dustproof manner, curing to obtain the high-hardness easy-to-clean coating, and performing performance test, wherein the result is shown in the table 2.
Examples 2 to 4
Examples 2-4 differ from example 1 in that coating mixture iii was prepared according to the respective composition formulations specified in table 1, and the results of the high hardness easy-clean coating property test are shown in table 2.
Example 5
In contrast to example 1, the coated substrate was 304 stainless steel, and the results of the high hardness easy-clean coating property test are shown in table 2.
Example 6
In contrast to example 2, the mercaptopropyltriethoxysilane and chloroform in S1 were changed to gamma-mercaptopropyltrimethoxysilane and ethyl acetate, respectively, and the coating substrate used was 304 stainless steel, the results of the high hardness easy-to-clean coating performance test are shown in Table 2.
Example 7
In contrast to example 3, the mercaptopropyltriethoxysilane and chloroform in S1 were replaced with alpha-mercaptomethyltriethoxysilane and xylene, respectively, and the coating substrate used was 304 stainless steel, resulting in high hardness easy-to-clean coating performance test results as shown in Table 2.
Example 8
In contrast to example 4, the coated substrate was 304 stainless steel, and the results of the high hardness easy-clean coating property test are shown in table 2.
Example 9
Different from example 5, according to the ratio of each component in table 1, adding the organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and dibutyltin laurate, mixing uniformly, and then diluting with a diluting solvent to obtain a coating mixture liquid III, wherein the test results of the performance of the high-hardness easy-cleaning coating are shown in table 2.
Example 10
Different from example 4, according to the ratio of each component in table 1, adding the organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and dibutyltin laurate, mixing uniformly, and then diluting with a diluting solvent to obtain a coating mixed solution III, wherein the test results of the performance of the high-hardness easy-cleaning coating are shown in table 2.
Example 11
Different from example 4, according to the ratio of each component in table 1, adding the organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and dibutyltin laurate, mixing uniformly, and then diluting with a diluting solvent to obtain a coating mixed solution III, wherein the test results of the performance of the high-hardness easy-cleaning coating are shown in table 2.
Example 12
Different from example 4, according to the ratio of each component in table 1, adding the organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyl trimethoxy silane, gamma- (2, 3-epoxypropoxy) propyl trimethoxy silane and dibutyltin laurate, mixing uniformly, and then diluting with a diluting solvent to obtain a coating mixed solution III, wherein the test results of the performance of the high-hardness easy-cleaning coating are shown in table 2.
Performance testing and results
The hardness of the coating is tested according to the national standard GB/T6739-2006, the adhesion is tested according to the national standard GB/T9286-89, and the easy-cleaning performance is tested by adopting an oil pen painting-scratch test and a water contact angle, and the results are shown in Table 2.
From the results, the physical property change trends of the treatment coatings with different concentrations are basically the same after the treatment coatings are completely cured and formed into films on two substrates, and the functional coating treatment solid content is 15%, so that better performance can be obtained.
The above-mentioned embodiments only express several embodiments of the present invention, and the description thereof is more specific and detailed, but not construed as limiting the scope of the present invention. It should be noted that, for a person skilled in the art, several variations and modifications can be made without departing from the inventive concept, which falls within the scope of the present invention. Therefore, the protection scope of the invention patent should be subject to the appended claims.
TABLE 1 mixture of III kinds of components and their mass fractions
Table 2 results of performance testing
Claims (6)
1. A high-hardness easy-to-clean coating prepared from organic silicon modified organic polysilazane is characterized by being prepared by the following steps: firstly, uniformly mixing organic silicon modified organic polysilazane, tetraethyl orthosilicate, methyltrimethoxysilane, gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane and a film-forming auxiliary agent, then diluting with a diluting solvent to obtain a coating mixed solution III, finally uniformly spraying the obtained coating mixed solution III onto a coating carrier by using a spray gun, and curing to obtain the high-hardness easy-to-clean coating;
the organic silicon modified organic polysilazane is prepared by the following steps:
s1. premix: firstly, dissolving organic polysilazane containing double bonds in a solvent system, then adding a coupling agent containing mercaptosilane, fully mixing, finally adding an initiator, and dissolving and mixing to obtain a mixed solution I;
s2, reaction: reacting the mixed solution I obtained in the step S1 under the conditions of stirring and ultraviolet light irradiation to obtain a mixed solution II;
s3, impurity removal: carrying out reduced pressure distillation on the mixed solution II obtained in the step S2 to obtain the organic silicon modified organic polysilazane;
wherein, the steps S1 to S3 are all performed in an oxygen-free environment;
the double bond-containing organic polysilazane of step S1 is a vinyl group-containing organic polysilazane, and the vinyl group-containing organic polysilazane is: one or more than two of organic polysilazane blocked by monovinyl, organic polysilazane blocked by divinyl and organic silicone polysilazane with vinyl on side chain or vinyl on ring;
the mercaptosilane coupling agent of step S2 is one or more of mercaptopropyltriethoxysilane, gamma-mercaptopropyltrimethoxysilane, gamma-mercaptopropylmethyldiethoxysilane, gamma-mercaptopropylmethyldimethoxysilane, gamma-mercaptopropylisopropoxysilane and alpha-mercaptomethyltriethoxysilane.
2. The high-hardness easy-to-clean coating prepared from the organosilicon modified organic polysilazane of claim 1, wherein the solvent system of step S1: one or more of isopropanol, ethanol, ethyl acetate, n-butyl ether, propylene glycol monomethyl ether, toluene, xylene, chloroform, and xylene.
3. The high-hardness easy-to-clean coating prepared from the organosilicon modified organic polysilazane as claimed in claim 1, wherein the reaction in step S2 is performed at room temperature, the wavelength of the ultraviolet light is 350-370nm, and the irradiation time is 20-40 min.
4. The high-hardness easy-to-clean coating prepared from the organic silicon modified organic polysilazane of claim 1, wherein the organic film-forming aid is dibutyltin laurate.
5. The high-hardness easy-to-clean coating prepared from the organic silicon modified organic polysilazane as claimed in claim 4, wherein the solid content of the coating mixed solution III is 10% -20%, and the coating carrier is one of glass, metal or wood.
6. The high-hardness easy-cleaning coating prepared from the organosilicon modified organic polysilazane of claim 5, wherein the thickness of the high-hardness easy-cleaning coating obtained by curing is 80-120 μm.
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