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 PDF

Info

Publication number
CN110903484B
CN110903484B CN201911254137.9A CN201911254137A CN110903484B CN 110903484 B CN110903484 B CN 110903484B CN 201911254137 A CN201911254137 A CN 201911254137A CN 110903484 B CN110903484 B CN 110903484B
Authority
CN
China
Prior art keywords
organic
polysilazane
coating
organic polysilazane
easy
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Active
Application number
CN201911254137.9A
Other languages
Chinese (zh)
Other versions
CN110903484A (en
Inventor
汪清云
王柱
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Hunan Yuhong New Material Technology Co.,Ltd.
Original Assignee
Hunan Yuhong New Material Technology Co ltd
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hunan Yuhong New Material Technology Co ltd filed Critical Hunan Yuhong New Material Technology Co ltd
Priority to CN201911254137.9A priority Critical patent/CN110903484B/en
Publication of CN110903484A publication Critical patent/CN110903484A/en
Application granted granted Critical
Publication of CN110903484B publication Critical patent/CN110903484B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • CCHEMISTRY; METALLURGY
    • C08ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08GMACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G77/00Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
    • C08G77/60Macromolecular 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
    • C08G77/62Nitrogen atoms
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D183/00Coating 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
    • C09D183/16Coating 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
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D7/00Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/40Additives
    • C09D7/60Additives non-macromolecular
    • C09D7/63Additives non-macromolecular organic

Landscapes

  • 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)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)

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

Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same
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
Figure BDA0002308183390000021
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
Figure BDA0002308183390000061
Figure BDA0002308183390000071
Table 2 results of performance testing
Figure BDA0002308183390000072
Figure BDA0002308183390000081

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.
CN201911254137.9A 2019-12-09 2019-12-09 Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same Active CN110903484B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN201911254137.9A CN110903484B (en) 2019-12-09 2019-12-09 Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN201911254137.9A CN110903484B (en) 2019-12-09 2019-12-09 Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same

Publications (2)

Publication Number Publication Date
CN110903484A CN110903484A (en) 2020-03-24
CN110903484B true CN110903484B (en) 2022-02-08

Family

ID=69823693

Family Applications (1)

Application Number Title Priority Date Filing Date
CN201911254137.9A Active CN110903484B (en) 2019-12-09 2019-12-09 Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same

Country Status (1)

Country Link
CN (1) CN110903484B (en)

Families Citing this family (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP7140040B2 (en) 2019-04-17 2022-09-21 信越化学工業株式会社 Alkoxysilyl group-containing organic silazane compound, method for producing the same, composition and cured product containing the same
CN113549349A (en) * 2020-04-25 2021-10-26 泰兴瑞深新材科技有限公司 Preparation method of surface treating agent for pipette tip
CN111621228A (en) * 2020-07-01 2020-09-04 广东威凯表面技术有限公司 Easy-to-clean coating with high hardness and high toughness
CN112322186B (en) * 2020-10-26 2022-06-21 华帝股份有限公司 Anticorrosive paint and preparation method and application thereof
CN112879269B (en) * 2021-01-29 2023-04-11 宁波东洲传动件有限公司 U-shaped joint for air cylinder and preparation method thereof
CN113174049B (en) * 2021-04-08 2022-10-25 华南理工大学 Modified organic polysilazane modified based on long-chain alkyl compound and preparation method and application thereof
CN115772268B (en) * 2021-09-08 2023-09-15 涂创时代(苏州)科技开发有限公司 Modified polysilazane nanocomposite and preparation method and application thereof
CN114561149A (en) * 2022-03-11 2022-05-31 江西师范大学 Superhard polysilazane easy-to-clean coating and preparation method thereof
CN114349536B (en) * 2022-03-21 2022-06-21 广东简一(集团)陶瓷有限公司 Anti-fouling nano easy-cleaning liquid and preparation method thereof, and preparation method of anti-fouling nano easy-cleaning ceramic

Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101020750A (en) * 2007-03-16 2007-08-22 西北工业大学 Silicone antifoulant and its prepn
CN102827496A (en) * 2012-09-17 2012-12-19 张家港楚人新材料科技有限公司 Method for packaging and modifying surface of substance
CN103913966A (en) * 2012-12-28 2014-07-09 佳能株式会社 Toner
CN105531332A (en) * 2013-09-13 2016-04-27 巴斯夫欧洲公司 Scratch-resistant radiation-cured coatings
CN106459482A (en) * 2014-02-28 2017-02-22 Az电子材料(卢森堡)责任有限公司 Hybrid material for optoelectronic applications
CN106612617A (en) * 2014-06-19 2017-05-03 英克伦股份有限公司 Composition having siloxane polymer and particle
CN106751894A (en) * 2016-12-02 2017-05-31 镇江高美新材料有限公司 A kind of resistant to elevated temperatures antimicrobial form liquid silastic and preparation method thereof
CN107236453A (en) * 2012-07-03 2017-10-10 伯宁布什集团有限公司 Silicon substrate high performance paint composition
CN107722283A (en) * 2017-11-02 2018-02-23 合众(佛山)化工有限公司 A kind of superhard organic silicon hydrophobic glass resin and preparation method thereof
CN109485853A (en) * 2017-09-11 2019-03-19 中国科学院化学研究所 A kind of polysiloxanes/Perhydropolysilazane hybridized polymer and its synthetic method
CN110092873A (en) * 2019-05-16 2019-08-06 广东工业大学 A kind of photosensitive resin ceramics and its Stereo Lithography preparation method
CN110128664A (en) * 2019-04-04 2019-08-16 华南理工大学 Modification organopolysilazane and its preparation method and application based on fluorochemical modification
CN110205025A (en) * 2019-05-28 2019-09-06 华南理工大学 It is a kind of using organopolysilazane as super-hydrophilic coating of anchor molecule and preparation method thereof

Patent Citations (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN101020750A (en) * 2007-03-16 2007-08-22 西北工业大学 Silicone antifoulant and its prepn
CN107236453A (en) * 2012-07-03 2017-10-10 伯宁布什集团有限公司 Silicon substrate high performance paint composition
CN102827496A (en) * 2012-09-17 2012-12-19 张家港楚人新材料科技有限公司 Method for packaging and modifying surface of substance
CN103913966A (en) * 2012-12-28 2014-07-09 佳能株式会社 Toner
CN105531332A (en) * 2013-09-13 2016-04-27 巴斯夫欧洲公司 Scratch-resistant radiation-cured coatings
CN106459482A (en) * 2014-02-28 2017-02-22 Az电子材料(卢森堡)责任有限公司 Hybrid material for optoelectronic applications
CN106612617A (en) * 2014-06-19 2017-05-03 英克伦股份有限公司 Composition having siloxane polymer and particle
CN106751894A (en) * 2016-12-02 2017-05-31 镇江高美新材料有限公司 A kind of resistant to elevated temperatures antimicrobial form liquid silastic and preparation method thereof
CN109485853A (en) * 2017-09-11 2019-03-19 中国科学院化学研究所 A kind of polysiloxanes/Perhydropolysilazane hybridized polymer and its synthetic method
CN107722283A (en) * 2017-11-02 2018-02-23 合众(佛山)化工有限公司 A kind of superhard organic silicon hydrophobic glass resin and preparation method thereof
CN110128664A (en) * 2019-04-04 2019-08-16 华南理工大学 Modification organopolysilazane and its preparation method and application based on fluorochemical modification
CN110092873A (en) * 2019-05-16 2019-08-06 广东工业大学 A kind of photosensitive resin ceramics and its Stereo Lithography preparation method
CN110205025A (en) * 2019-05-28 2019-09-06 华南理工大学 It is a kind of using organopolysilazane as super-hydrophilic coating of anchor molecule and preparation method thereof

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
乙烯基硅氮烷-巯基共聚物热裂解研究;陈立新等;《化学学报》;20090614;第67卷(第11期);第1182-1188页 *
巯基/乙烯基硅氮烷紫外光固化的研究;宋家乐等;《影像科学与光化学》;20080531;第26卷(第3期);第218-223页 *

Also Published As

Publication number Publication date
CN110903484A (en) 2020-03-24

Similar Documents

Publication Publication Date Title
CN110903484B (en) Organic silicon modified organic polysilazane and high-hardness easy-to-clean coating prepared from same
CN108906557B (en) Long-acting super-hydrophilic polysilazane coating and preparation method thereof
CN111117376B (en) Primer for silane modified building sealant
CN104072781B (en) SiH in a kind of molecular structure2and SiH1the controlled Perhydropolysilazane of ratio and hydrophobic transparent high hardness spray coating prepared therefrom and synthetic method thereof
US4233428A (en) Primer compositions for silicone rubber compositions
TW574735B (en) Method of film formation on a semiconductor substrate and the insulating film formed thereby
EP2130850A1 (en) Curable fluoripolyether coating compositions
JP2007111645A5 (en)
US20030158351A1 (en) Phenylethynyl-containing imide silanes
WO2015187766A1 (en) Adhesion primer for glass and ceramics
CN101508852B (en) Glass-hard organosilicon protective coating, preparation and uses thereof
JP5790480B2 (en) Acid anhydride group-containing organosiloxane and method for producing the same
US10696788B2 (en) Surface treatment agent
CN110387191B (en) Hydrophobic coating, preparation method thereof and hydrophobic coating solution
CN113773501A (en) Preparation method of curable silicon-based hybrid resin
CN113999613A (en) Solvent-free anti-doodling coating capable of being cured at room temperature
CN112724409A (en) UV (ultraviolet) photocuring multifunctional epoxy reactive diluent and preparation method thereof
JP2008255143A (en) Silicon fine particles, method for producing the same, solar cell by using the same, and method for producing solar cell
TWI637977B (en) Surface treatment agent
CN105384901A (en) Preparation method of bottom coating penetrant specially used for concrete joint sealant
KR100798745B1 (en) Anti-fog composition and manufacturing method thereby, anti-fog coatings
CN107011763B (en) Aqueous composition containing [3- (2, 3-dihydroxypropyl-1-oxy) propyl ] silanol oligomer, preparation method and application
CN115637096B (en) High-wear-resistance coating liquid composition and preparation method thereof
CN115340821B (en) Metal-based high-strength room-temperature-cured phenylamide ester-based silicone protective coating as well as preparation method and application thereof
CN108203502B (en) Water-soluble cross-linking agent and application thereof in water-based resin

Legal Events

Date Code Title Description
PB01 Publication
PB01 Publication
SE01 Entry into force of request for substantive examination
SE01 Entry into force of request for substantive examination
TA01 Transfer of patent application right

Effective date of registration: 20220105

Address after: 412000 No. 101, building D1, Kechuang Industrial Park, Nanzhou Town, Lukou District, Zhuzhou City, Hunan Province

Applicant after: Hunan Yuhong New Material Technology Co.,Ltd.

Address before: 412000 No. 10, Hejia group, Tangshi village, Longchuan Town, Zhuzhou County, Zhuzhou City, Hunan Province

Applicant before: ZHUZHOU XINXIANGYU ENVIRONMENT PROTECTION TECHNOLOGY Co.,Ltd.

TA01 Transfer of patent application right
GR01 Patent grant
GR01 Patent grant