CN115820046B - Silicone sealant primer and preparation method thereof - Google Patents

Silicone sealant primer and preparation method thereof Download PDF

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CN115820046B
CN115820046B CN202211716864.4A CN202211716864A CN115820046B CN 115820046 B CN115820046 B CN 115820046B CN 202211716864 A CN202211716864 A CN 202211716864A CN 115820046 B CN115820046 B CN 115820046B
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parts
silicone sealant
primer
chitosan
sealant primer
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CN115820046A (en
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李牧洁
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Guangzhou Baiyun Technology Co ltd
Guangdong Baiyun Technology Co Ltd
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Guangzhou Baiyun Chemical Industry Co Ltd
Guangdong Baiyun Technology Co Ltd
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    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02EREDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00Energy generation through renewable energy sources
    • Y02E10/50Photovoltaic [PV] energy

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Abstract

The invention discloses a silicone sealant primer and a preparation method thereof, wherein the silicone sealant primer is prepared from the following raw materials in parts by weight: 20-45 parts of chitosan, 10-109 parts of cross-linking agent, 14-99 parts of grafting modifier, 0.3-5.6 parts of catalyst, 1-3 parts of hollow microsphere and 50-100 parts of solvent. Wherein the cross-linking agent is one or more of glyoxal, glutaraldehyde, terephthalaldehyde, methylene bisacrylamide and epichlorohydrin; the grafting modifier is one or more of thioglycollic acid, mercaptopropionic acid, cysteine, vinyl acetic acid and vinyl formic acid. The silicone sealant primer can provide excellent low-temperature-resistant adhesion, and can establish a stable chemical bridge between the silicone sealant and a metal substrate under a low-temperature condition, so that the problem that the silicone sealant primer is not firmly adhered to the metal substrate under a low-temperature environment is effectively solved.

Description

Silicone sealant primer and preparation method thereof
Technical Field
The invention belongs to the technical field of sealants, and particularly relates to a silicone sealant primer and a preparation method thereof.
Background
The silicone sealant for the building has the advantages of excellent weather resistance, high and low temperature resistance, corrosion resistance and the like after being cured, and is widely applied to the building fields of curtain walls, interior decoration and the like, and plays roles of bonding and sealing. However, the silicone sealant has fewer polar groups connected to the Si-O chain, so that the bonding property with the metal substrate is poor, the silicone sealant is pasty before being cured, the fluidity on the surface of the metal substrate is poor, and the bonded metal substrate cannot be wetted well, so that the bonding effect with the metal substrate is affected.
For the phenomenon of weak adhesion of metal substrates, a primer is generally used for solving the problem. The primer is a solution substance which is coated on the base material in advance in the sealant construction process, and can form a firm thin layer on the surface of the base material after solidification. The thin layer is used as a transition layer between the sealant and the substrate and generally contains two functional groups, and can respectively form chemical bonds with the surface active functional groups of the substrate and the organic functional groups in the sealant, so that the bonding force between the thin layer and the sealant and between the substrate is superior to that between the sealant and the substrate, and the bonding performance between the sealant and the substrate is enhanced. However, under the low-temperature environment in winter, the reaction activity of the primer is slowed down, the chemical bonding points with the surface of the metal substrate are reduced, and the debonding phenomenon with different degrees is caused with the metal substrate, so that the development of the primer with low-temperature resistance and excellent cohesiveness has application value.
Disclosure of Invention
The invention aims to provide a silicone sealant primer, which can provide excellent cohesiveness in a low-temperature environment and effectively solve the problem that the conventional silicone sealant primer is not firmly adhered to a metal substrate in the low-temperature environment.
The technical scheme for achieving the aim comprises the following steps.
In one aspect, the invention provides a silicone sealant primer coating liquid which is prepared from the following raw materials in parts by weight:
the cross-linking agent is one or more of glyoxal, glutaraldehyde, terephthalaldehyde, methylene bisacrylamide and epichlorohydrin;
the grafting modifier is one or more of thioglycollic acid, mercaptopropionic acid, cysteine, vinyl acetic acid and vinyl formic acid;
the hollow microsphere is a hollow powder structure with components comprising silicon dioxide and calcium oxide; the main components of the hollow microsphere are silicon dioxide and calcium oxide, but other components such as sodium oxide, boron oxide and the like can be also included, wherein the silicon dioxide and the calcium oxide account for 70-95% of the total mass.
In some embodiments, the composition is prepared from the following raw materials in parts by weight:
in some embodiments, the chitosan is 34 to 36 parts by weight.
In some of these embodiments, the grafting modifier is present in an amount of 22 to 70 parts by weight.
In some of these embodiments, the hollow microspheres have a diameter of 5 μm to 30 μm.
In some embodiments, the chitosan is a macromolecular linear polymer having a degree of deacetylation greater than or equal to 95% and a viscosity of 50mpa.s to 100 mpa.s.
In some of these embodiments, the catalyst is an organometallic complex catalyst.
In some of these embodiments, the catalyst is one or more of dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin dioctanoate, isopropyl titanate, t-butyl titanate, isopropyl tris (dioctyl pyrophosphoryl) titanate.
In some of these embodiments, the solvent is a mixture of isopropanol with xylene and/or ethyl acetate.
In some of these embodiments, the weight ratio of the xylene and/or ethyl acetate to the isopropyl alcohol is 1:0.6-0.9.
In one aspect of the invention, a preparation method of a silicone sealant primer based on the above is provided, which comprises the following steps:
adding chitosan into a solvent, stirring until the chitosan is dissolved, adding a cross-linking agent, uniformly stirring, and reacting for 0.5-5 h at 20-50 ℃ to prepare chitosan resin;
adding a grafting modifier into the chitosan resin, and uniformly stirring to obtain a grafting modified chitosan resin;
sequentially adding a solvent, hollow microspheres and a catalyst into the grafted modified chitosan resin, and uniformly stirring to obtain the silicone sealant primer.
The inventor of the present invention found that the conventional silicone sealant primer exhibits poor adhesion at low temperature, and is mainly characterized by a large area of non-tackiness at a relatively short curing time, and a punctiform non-tackiness with an increase in curing time. The main reason for the occurrence of the above phenomenon is that under low temperature conditions, the reactivity of the primer is reduced, the chemical bonding point with the surface of the metal substrate is reduced, and the adhesion to the metal substrate is not high. On the basis, the inventor researches and obtains the sealant primer provided by the invention, and the sealant primer can realize that the sealant primer has good bonding performance on metal substrates with different surface characteristics at low temperature.
The silicone sealant primer is prepared by mixing macromolecular polymer-chitosan with low cost and more active groups, a cross-linking agent, a grafting modifier, a catalyst, hollow microspheres and a solvent. Wherein the chitosan is crosslinked with-NH in chitosan by a crosslinking agent 2 The chitosan resin with a reticular cross-linked structure retaining an-OH side chain is generated by a cross-linking reaction, so that a thin layer is easily formed on the surface of a metal substrate after the primer is solidified, the surface activity of the metal substrate is increased, and the adhesive force to the metal substrate is improved; -COOH in the grafting modifier and-NH in the chitosan resin 2 Amidation or esterification reaction is carried out on the/(OH), mercapto and/or vinyl groups are introduced, so that the surface cross-linking curing degree of the sealing glue is improved; by adding the hollow microspheres, the fluidity and spreading uniformity of the base coat are enhanced, the bonding effect is prevented from being influenced by too thick or too thin base coat which is brushed, and the construction is also facilitated. The components interact and cooperate, so that the obtained silicone sealant primer has more difunctional groups, better compatibility and excellent low-temperature-resistant adhesion, and a stable chemical bridge can be established between the silicone sealant and the metal substrate under the low-temperature condition to replace a silane coupling agent in the traditional primer, thereby effectively solving the problem that the silicone sealant primer is not firmly adhered to the metal substrate under the low-temperature environment.
Detailed Description
The present invention will be described more fully hereinafter in order to facilitate an understanding of the present invention. This invention may be embodied in many different forms and is not limited to the embodiments described herein. Rather, these embodiments are provided so that this disclosure will be thorough and complete.
The experimental procedures, which do not address the specific conditions in the examples below, are generally carried out under conventional conditions or under conditions recommended by the manufacturer. The various chemicals commonly used in the examples are commercially available.
Unless defined otherwise, all technical and scientific terms used herein have the same meaning as commonly understood by one of ordinary skill in the art to which this invention belongs. The terminology used in the description of the invention herein is for the purpose of describing particular embodiments only and is not intended to be limiting of the invention. The term "and/or" as used herein includes any and all combinations of one or more of the associated listed items.
Example 1
The preparation method of the silicone sealant primer provided by the embodiment comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 30 parts of isopropanol, stirring until the chitosan is dissolved, adding 18 parts of glyoxal (40% of mass fraction), stirring uniformly, and reacting at 40 ℃ for 1h to obtain chitosan resin;
adding 23 parts of thioglycollic acid into the chitosan resin, and uniformly stirring and mixing to obtain grafted modified chitosan resin;
45 parts of ethyl acetate, 1.6 parts of hollow microsphere (C100 of China star with the diameter of 5-30 mu m) and 0.8 part of isopropyl titanate are sequentially added into the grafted modified chitosan resin, and the mixture is fully and uniformly stirred to prepare the silicone sealant primer.
Example 2
The preparation method of the silicone sealant primer provided by the embodiment comprises the following steps:
dissolving 20 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 30 parts of isopropanol, stirring until the chitosan is dissolved, adding 27 parts of glutaraldehyde (the mass fraction of glutaraldehyde is 25%), stirring uniformly, and reacting at 35 ℃ for 2 hours to obtain chitosan resin;
29 parts of mercaptopropionic acid is added into the chitosan resin, and the grafted modified chitosan resin is prepared by stirring and mixing uniformly;
45 parts of dimethylbenzene, 1.6 parts of hollow microsphere (C100 of China star with the diameter of 5-30 mu m) and 0.9 part of tert-butyl titanate are sequentially added into the grafted and modified chitosan resin, and the mixture is fully stirred to prepare the silicone sealant primer.
Example 3
The preparation method of the silicone sealant primer provided by the embodiment comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 40 parts of isopropanol, stirring until the chitosan is dissolved, adding 73 parts of terephthalaldehyde, stirring uniformly, and reacting for 3 hours at 45 ℃ to obtain chitosan resin;
66 parts of cysteine is added into the chitosan resin, and the grafting modified chitosan resin is prepared by stirring and mixing uniformly;
45 parts of dimethylbenzene, 1.6 parts of hollow microsphere (C100 of China star with the diameter of 5-30 mu m) and 4.7 parts of isopropyl tri (dioctyl pyrophosphoric acid acyloxy) titanate are sequentially added into the grafted modified chitosan resin, and the mixture is fully stirred to prepare the silicone sealant primer.
Example 4:
the embodiment provides a preparation method of a silicone sealant primer, which comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 40 parts of isopropanol, stirring until the chitosan is dissolved, adding 36 parts of methylene bisacrylamide, stirring uniformly, and reacting for 4 hours at 40 ℃ to obtain chitosan resin;
adding 14 parts of vinyl acetic acid into the chitosan resin, and uniformly stirring and mixing to obtain grafted modified chitosan resin;
45 parts of ethyl acetate, 1.6 parts of hollow microsphere (C100 of China star with the diameter of 5-30 mu m) and 0.6 part of dibutyl tin dilaurate are sequentially added into the grafted modified chitosan resin, and the mixture is fully stirred to prepare the silicone sealant primer.
Example 5:
the embodiment provides a preparation method of a silicone sealant primer, which comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 30 parts of isopropanol, stirring until the chitosan is dissolved, adding 25 parts of epichlorohydrin, stirring uniformly, and reacting for 2 hours at 40 ℃ to obtain chitosan resin;
17 parts of vinyl formic acid is added into the chitosan resin, and the grafting modified chitosan resin is prepared by stirring and mixing uniformly;
and sequentially adding 35 parts of ethyl acetate, 0.8 part of hollow microsphere (C100 of China star with the diameter of 5-30 mu m) and 0.5 part of dibutyl tin diacetate into the grafted modified chitosan resin, and fully stirring to obtain the silicone sealant primer.
Comparative example 1:
the area of the silicone sealant primer provided in this comparative example with example 1 is: the other components and preparation method were the same as in example 1 without adding the graft modifier. The preparation method comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 30 parts of isopropanol, stirring until the chitosan is dissolved, adding 18 parts of glyoxal (40% of mass fraction), stirring uniformly, and reacting at 40 ℃ for 1h to obtain chitosan resin;
45 parts of ethyl acetate, 1.6 parts of hollow microsphere (C100 of China star with the diameter of 5-30 μm) and 0.8 part of isopropyl titanate are sequentially added into chitosan resin, and the mixture is fully stirred to prepare the silicone sealant primer.
Comparative example 2:
the area of the silicone sealant primer provided in this comparative example with example 1 is: without adding hollow microspheres, other components and preparation methods are the same as those of the embodiment 1. The preparation method comprises the following steps:
dissolving 35 parts of chitosan (R013967 of Roen, deacetylation degree of 95% and viscosity of 50-100 mpa.s) in 30 parts of isopropanol, stirring until the chitosan is dissolved, adding 18 parts of glyoxal (40% of mass fraction), stirring uniformly, and reacting at 40 ℃ for 1h to obtain chitosan resin;
adding 23 parts of thioglycollic acid into the chitosan resin, and uniformly stirring and mixing to obtain grafted modified chitosan resin;
45 parts of ethyl acetate and 0.8 part of isopropyl titanate are sequentially added into the grafted modified chitosan resin, and the mixture is fully stirred to prepare the silicone sealant primer.
TABLE 1 list of the amounts (parts by weight) of the raw material components of examples and comparative examples
Description of the preferred embodiments Chitosan Crosslinking agent Grafting modifier Hollow micro-bead Catalyst Solvent(s)
Example 1 35 18 23 1.6 0.8 75
Example 2 20 27 29 1.6 0.9 75
Example 3 35 73 66 1.6 4.7 85
Example 4 35 36 14 1.6 0.6 85
Example 5 35 25 17 0.8 0.5 65
Comparative example 1 35 18 0 1.6 0.8 75
Comparative example 2 35 18 23 0 0.8 75
The silicone sealant primers prepared in examples 1-5 and comparative examples 1-2 were tested for adhesion to various metal substrates by the following procedure:
the silicone sealant base solutions prepared in examples and comparative examples were placed in a constant temperature and humidity cabinet (temperature 0 ℃ + -0.2 ℃, humidity 50% + -5%) for 1 day. And (3) after low-temperature treatment, taking out, coating onto a test metal substrate, drying for 5 minutes, carrying out Shi Shuang component dealcoholized silicone structural sealant (selected from Guangzhou white cloud chemical industry), continuously placing in a constant-temperature constant-humidity box (the temperature is 0+/-0.2 ℃ and the humidity is 50+/-5%) after construction, carrying out low-temperature maintenance for 16 hours, and taking out of the room for normal-temperature peeling test. The results of the test are shown in Table 2, with a two-component dealcoholized silicone sealer applied directly without brushing the silicone sealer primer as a control.
TABLE 2 Low temperature adhesion test of two-component dealcoholized sealants and various Metal substrates
Description of the preferred embodiments Anodized aluminum Fluorocarbon sprayed aluminum Powder spraying aluminum Stainless steel Galvanized steel sheet
Example 1 100%CF 100%CF 100%CF 100%CF 100%CF
Example 2 75%CF 70%CF 70%CF 65%CF 65%CF
Example 3 100%CF 100%CF 100%CF 100%CF 100%CF
Example 4 80%CF 80%CF 80%CF 80%CF 70%CF
Example 5 90%CF 90%CF 90%CF 90%CF 80%CF
Comparative example 1 65%CF 60%CF 60%CF 65%CF 60%CF
Comparative example 2 85%CF 85%CF 85%CF 80%CF 80%CF
Comparative example 25%CF 15%CF 15%CF 10%CF 10%CF
Note that: CF represents cohesive failure, with a larger number indicating better adhesion.
As is clear from Table 2, the comparative example in which the primer was not used had poor low-temperature adhesion. The silicone sealant primer prepared in the examples 1-5 has obvious improvement effect on the low-temperature adhesion of dealcoholized silicone sealant and various metal substrates; in comparison with example 2 and example 1, the silicone sealant primer has less chitosan and exhibits a relatively large area of non-tackiness. Compared with the examples 3-4 and the example 1, the silicone sealant primer has the advantages that the dosage of the cross-linking agent and the grafting modifier is small, the film forming effect of the primer is slightly poor, the interface destruction area is large, and the content of the grafting modifier in the primer is a key factor influencing the low-temperature-resistant bonding performance of the primer. In comparison with example 1, when the amount of hollow microspheres in the silicone sealant primer is reduced to half, the cured thin layer of the silicone sealant primer is uneven, the surface drying time is slightly prolonged, and the punctiform non-sticking condition appears, which indicates that the hollow microspheres in the silicone sealant primer can improve the uniformity and fluidity of the primer, and provides guarantee for uniform spreading of the silicone sealant primer.
Therefore, the silicone sealant primer provided by the invention can provide excellent low-temperature-resistant adhesion, and the problem that the silicone sealant primer is not firmly adhered to a metal substrate in a low-temperature environment is effectively solved, so that stable adhesion between the silicone sealant and the metal substrate is realized in the low-temperature condition.
The technical features of the above-described embodiments may be arbitrarily combined, and all possible combinations of the technical features in the above-described embodiments are not described for brevity of description, however, as long as there is no contradiction between the combinations of the technical features, they should be considered as the scope of the description.
The above examples illustrate only a few embodiments of the invention, which are described in detail and are not to be construed as limiting the scope of the invention. It should be noted that it will be apparent to those skilled in the art that several variations and modifications can be made without departing from the spirit of the invention, which are all within the scope of the invention. Accordingly, the scope of protection of the present invention is to be determined by the appended claims.

Claims (8)

1. The silicone sealant primer is characterized by being prepared from the following raw materials in parts by weight:
34-36 parts of chitosan
16-80 parts of cross-linking agent
22-70 parts of grafting modifier
0.3-5.6 parts of catalyst
1-3 parts of hollow microsphere
50-100 parts of a solvent;
the cross-linking agent is one or more of glyoxal, glutaraldehyde, terephthalaldehyde, methylene bisacrylamide and epichlorohydrin;
the grafting modifier is one or more of thioglycollic acid, mercaptopropionic acid, cysteine, vinyl acetic acid and vinyl formic acid;
the hollow microsphere is a hollow powder structure with components comprising silicon dioxide and calcium oxide;
the solvent is a mixture of isopropanol and xylene and/or ethyl acetate.
2. The silicone sealant primer of claim 1, wherein the primer is prepared from the following raw materials in parts by weight:
35 parts of chitosan
16-80 parts of cross-linking agent
23-66 parts of grafting modifier
0.5-4.7 parts of catalyst
1.1-2.3 parts of hollow microsphere
65-85 parts of a solvent.
3. The silicone sealant primer of claim 1, wherein the hollow microspheres have a diameter of 5 μm to 30 μm.
4. The silicone sealant primer of claim 1, wherein the chitosan is a macromolecular linear polymer having a deacetylation degree of not less than 95% and a viscosity of 50mpa.s to 100 mpa.s.
5. The silicone sealant primer of claim 1, wherein the catalyst is an organometallic complex catalyst.
6. The silicone sealant primer of claim 5, wherein the catalyst is one or more of dibutyl tin dilaurate, dibutyl tin diacetate, dibutyl tin dioctanoate, isopropyl titanate, t-butyl titanate, isopropyl tris (dioctyl pyrophosphoryloxy) titanate.
7. The silicone sealant primer of claim 1, wherein the weight ratio of the xylene and/or ethyl acetate to the isopropyl alcohol is 1:0.6-0.9.
8. A method for preparing a silicone sealant primer solution according to any one of claims 1 to 7, comprising the steps of:
adding chitosan into a solvent, stirring until the chitosan is dissolved, adding a cross-linking agent, uniformly stirring, and reacting for 0.5-5 h at 20-50 ℃ to obtain chitosan resin;
adding a grafting modifier into the chitosan resin, and uniformly stirring to obtain a grafting modified chitosan resin;
sequentially adding a solvent, hollow microspheres and a catalyst into the grafted modified chitosan resin, and uniformly stirring to obtain the silicone sealant primer.
CN202211716864.4A 2022-12-29 2022-12-29 Silicone sealant primer and preparation method thereof Active CN115820046B (en)

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Citations (5)

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Publication number Priority date Publication date Assignee Title
JP2003201576A (en) * 2002-01-11 2003-07-18 Nippon Parkerizing Co Ltd Aqueous surface preparation agent, surface preparation method and surface-prepared material
FI20085543A0 (en) * 2008-06-03 2008-06-03 Upm Kymmene Corp Release material composition, base material and method for making base material, surface treatment agent for base material and use of surface treatment agent
CN101336272A (en) * 2006-01-25 2008-12-31 大日精化工业株式会社 Hydroxyalkylated chitosan solution
WO2011082706A2 (en) * 2010-01-07 2011-07-14 Ringo Grombe Surface modification system for coating substrate surfaces
WO2014030208A1 (en) * 2012-08-21 2014-02-27 大日精化工業株式会社 Aqueous liquid composition, aqueous coating liquid, funtional coating film and composite material

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US11795320B2 (en) * 2019-09-20 2023-10-24 Bausch + Lomb Ireland Limited Grafted polymer and use thereof

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2003201576A (en) * 2002-01-11 2003-07-18 Nippon Parkerizing Co Ltd Aqueous surface preparation agent, surface preparation method and surface-prepared material
CN101336272A (en) * 2006-01-25 2008-12-31 大日精化工业株式会社 Hydroxyalkylated chitosan solution
FI20085543A0 (en) * 2008-06-03 2008-06-03 Upm Kymmene Corp Release material composition, base material and method for making base material, surface treatment agent for base material and use of surface treatment agent
WO2011082706A2 (en) * 2010-01-07 2011-07-14 Ringo Grombe Surface modification system for coating substrate surfaces
WO2014030208A1 (en) * 2012-08-21 2014-02-27 大日精化工業株式会社 Aqueous liquid composition, aqueous coating liquid, funtional coating film and composite material

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