CN116217804A - Organosilicon hybrid composite material and preparation method and application thereof - Google Patents

Organosilicon hybrid composite material and preparation method and application thereof Download PDF

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CN116217804A
CN116217804A CN202211623570.7A CN202211623570A CN116217804A CN 116217804 A CN116217804 A CN 116217804A CN 202211623570 A CN202211623570 A CN 202211623570A CN 116217804 A CN116217804 A CN 116217804A
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hybrid composite
composite material
organic silicon
silicone
preparation
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杨淼
章小林
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Central Research Institute Of China Chemical Science And Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
    • C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
    • C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
    • C08F230/085—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon the monomer being a polymerisable silane, e.g. (meth)acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
    • C08F222/10—Esters
    • C08F222/1006—Esters of polyhydric alcohols or polyhydric phenols
    • C08F222/102—Esters of polyhydric alcohols or polyhydric phenols of dialcohols, e.g. ethylene glycol di(meth)acrylate or 1,4-butanediol dimethacrylate
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K5/00—Heat-transfer, heat-exchange or heat-storage materials, e.g. refrigerants; Materials for the production of heat or cold by chemical reactions other than by combustion
    • C09K5/08—Materials not undergoing a change of physical state when used
    • C09K5/14—Solid materials, e.g. powdery or granular
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2227—Oxides; Hydroxides of metals of aluminium
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/24—Acids; Salts thereof
    • C08K3/26—Carbonates; Bicarbonates
    • C08K2003/265—Calcium, strontium or barium carbonate

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  • Chemical & Material Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
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  • Health & Medical Sciences (AREA)
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  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
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  • Compositions Of Macromolecular Compounds (AREA)

Abstract

The invention relates to an organosilicon hybrid composite material, a preparation method and application thereof, and belongs to the technical field of thermal management materials. In the invention, the organic silicon hybrid composite material is cured on a heat conduction interface through free radical initiation. The organic silicon hybrid composite material comprises an organic silicon acrylic acid hybrid compound, a polyurethane hybrid polymer, a free radical initiator and a heat conducting filler. The composite material has better adhesive property while keeping low viscosity, high strength after complete curing and better water resistance.

Description

Organosilicon hybrid composite material and preparation method and application thereof
Technical Field
The invention relates to the technical field of thermal management materials, and particularly provides an organosilicon hybrid composite material, and a preparation method and application thereof.
Background
The resin materials used for the thermal management material at the present stage comprise organic silicon resin, polyurethane resin, MS resin, epoxy resin and the like, wherein the polyurethane resin and the epoxy resin have good strength and adhesiveness, the MS resin has good flexibility, and the organic silicon resin has good flexibility and weather resistance. The organic silicon resin has great advantages in flexible resin, has high temperature resistance and stability, has excellent weather resistance and durability, and can be made into a rubber elastomer with excellent performance. However, the organosilicon material needs two-component crosslinking curing or moisture curing, and the two-component material has faster curing, but more complex use process than the single-component material and higher requirements on equipment; the single-component material needs moisture curing or low-temperature storage, has the limitation of slow curing or harsh storage conditions, and the requirements of normal-temperature storage and quick curing require that the material has long-term storage property at room temperature and can be quickly cured after temperature rise.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides an organosilicon hybrid composite material, and a preparation method and application thereof. The invention uses the thermal management material solidified by the free radical mechanism, and can realize the rapid solidification after temperature rise when being matched with a proper ratio of the free radical initiator and the material.
In order to solve the technical problems, the invention provides the following technical scheme:
on the one hand, the invention provides an organic silicon hybrid composite material which is prepared from the following raw materials in parts by weight:
Figure BDA0004003491660000011
Figure BDA0004003491660000021
the structural formula of the organosilicon acrylic acid hybrid compound is as follows:
Figure BDA0004003491660000022
wherein R1 is a compound Containing (CH) 2 ) Or (OCH) 2 CH 2 ) Is a linking group of (a).
R2 is a linking group containing 6 to 30 carbon atoms.
Further, the structural formula of R2 is as follows:
Figure BDA0004003491660000023
Figure BDA0004003491660000031
preferably, the heat-conducting filler is one or more of aluminum oxide, silicon dioxide, zinc oxide, magnesium oxide, aluminum nitride, boron nitride, aluminum hydroxide, silicon nitride, silicon carbide and calcium carbonate; the particle size of the heat conductive filler is 0.5-300 microns, preferably 1-100 microns. Preferably, the weight ratio of alumina 70 microns, alumina 40 microns, alumina 20 microns and alumina 3 microns is 3:3:2:2.
Further, the free radical initiator is a cyano compound or an organic peroxide containing an azo group. Preference is given to azobisisobutyronitrile, azobisisoheptonitrile, benzoyl peroxide, dicumyl peroxide, t-butyl benzoyl peroxide and the like.
Further, the polymerization inhibitor is one or more of hydroquinone, 2, 6-di-tert-butyl-4-cresol (BHT), p-hydroxyanisole, phenothiazine, 4-hydroxy-2, 6-tetramethyl piperidine-1-oxygen free radical and 4- (2-aminoethyl) phenol.
Further, the solvent is one or more of mineral oil, vegetable oil, industrial white oil, liquid paraffin and silicone oil.
Further, the other double bond containing monomers are compounds containing one or more carbon-carbon double bond functional groups.
Preferably, the other monomer containing a double bond is an ester of methacrylic acid with an alcohol containing C1 to C12, a diester of methacrylic acid with a glycol containing C1 to C6, a triester of methacrylic acid with a triol containing C1 to C6, or an oligomer containing a methacrylic acid group. Preferred are triglycerides of methacrylic acid, triglycerides of acrylic acid, diethylene glycol methacrylate, ethylene glycol methacrylate pentaerythritol methacrylate, pentaerythritol acrylate, ethoxylated pentaerythritol acrylate, dipentaerythritol hexaacrylate and the like.
On the other hand, the invention also provides a preparation method of the organic silicon hybrid composite material, wherein the organic silicon hybrid composite material is cured on a heat conduction interface through free radical initiation; specific: mixing and stirring the organosilicon acrylic acid hybrid compound, the heat-conducting filler, the free radical initiator, the polymerization inhibitor, the solvent and other monomers containing double bonds uniformly.
In still another aspect, the invention further provides an application of the organic silicon hybrid composite material in the field of thermal management, wherein the organic silicon hybrid composite material is coated on a target surface on extrusion equipment, the thickness is 0.1-5 mm, and the organic silicon hybrid composite material is formed by heating, curing and molding, and is heated for 10 min-3 h at 80-200 ℃.
Compared with the prior art, the invention has the following beneficial effects:
the organic silicon hybrid composite material is cured on a heat conduction interface through free radical initiation, and has better bonding performance, water resistance and heat conductivity while keeping low viscosity. Meanwhile, all the substances are mixed, and solidification can be completed through heating, so that the preparation method is convenient for normal-temperature storage and transportation; and the curing is completed without adding other substances, so that the method is convenient and quick, and the preparation method is simple and convenient.
Detailed Description
In order to make the technical problems, technical solutions and advantages to be solved by the present invention more apparent, the following detailed description will be made with reference to specific embodiments.
The reagents and materials used in the examples and comparative examples of the present invention were commercially available unless otherwise specified.
The invention provides an organosilicon hybrid composite material, a preparation method and application thereof, and specific embodiments are as follows.
Example 1
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000041
the structural formula of the organosilicon acrylic acid hybrid compound is as follows:
Figure BDA0004003491660000051
wherein R1 is OCH 2 CH 2 The method comprises the steps of carrying out a first treatment on the surface of the R2 is (CH) 2 ) 6 。
Specific: mixing and stirring the organosilicon acrylic acid hybrid compound, the heat conducting filler, the free radical initiator, the polymerization inhibitor, the solvent and other monomers containing double bonds uniformly.
Example 2
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000052
the structural formula of the organosilicon acrylic acid hybrid compound is the same as that of the embodiment 1.
The preparation method is the same as in example 1.
Example 3
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000061
the structural formula of the organosilicon acrylic acid hybrid compound is the same as that of the embodiment 1.
The preparation method is the same as in example 1.
Example 4
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000062
the structural formula of the organosilicon acrylic acid hybrid compound is as follows:
Figure BDA0004003491660000071
wherein R1 is CH 2 。
The structural formula of R2 is as follows:
Figure BDA0004003491660000072
the preparation method is the same as in example 1.
Example 5
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000073
Figure BDA0004003491660000081
the structural formula of the organosilicon acrylic acid hybrid compound is as follows:
Figure BDA0004003491660000082
wherein R1 is OCH 2 CH 2 。
The structural formula of R2 is as follows:
Figure BDA0004003491660000083
the preparation method is the same as in example 1.
Example 6
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000084
Figure BDA0004003491660000091
the structure of the organosilicon acrylic hybrid compound is the same as in example 5.
The preparation method is the same as in example 1.
Example 7
The preparation method of the organic silicon hybrid composite material comprises the following raw materials in parts by weight:
Figure BDA0004003491660000092
the organosilicon acrylic acid hybrid compound has the following structure:
Figure BDA0004003491660000093
wherein R1 is OCH 2 CH 2 The method comprises the steps of carrying out a first treatment on the surface of the The R2 structure is as follows:
Figure BDA0004003491660000101
the preparation method is the same as in example 1.
The specific application is as follows: the material prepared in the embodiment is coated on the target surface on extrusion equipment, the thickness is 0.1-5 mm, and the material is formed by heating, solidifying and shaping, and the material is heated for 10 min-3 h at 80-200 ℃. The target object may be a chip or the like, and the above-mentioned materials may be heated and cured, so that the thermal conductivity, tensile strength and water resistance of the target sample can be improved.
To further highlight the beneficial effects of the present invention, the following comparative examples were constructed.
Comparative example 1
The heat conductive filler in this comparative example was 100 parts of aluminum oxide 70 μm, and the other conditions were the same as in example 1. The sample cannot flow.
Comparative example 2
The heat conductive filler in this comparative example was 100 parts of alumina 3 μm, and the other conditions were the same as in example 1. The viscosity of the sample is too high to prepare the sample.
Comparative example 3
In this comparative example, the heat conductive filler was omitted, and the other conditions were the same as in example 1.
Comparative example 4
In this comparative example, the silicone acrylic hybrid compound was replaced with an acrylic ester, and the other conditions were the same as in example 1.
Sample preparation and performance testing were performed on the materials prepared in the above examples and comparative examples according to the given standard requirements, with the sample curing temperature being 150 degrees for 30 minutes. The thermal conductivity was measured according to the standard ASTM D5470-2006 test method for thermal transmission performance standard of heat conductive and insulating materials, the tensile strength was measured according to the standard GB/T528-2009 determination of tensile stress strain performance of vulcanized rubber or thermoplastic rubber, the shear strength was measured according to the standard GB/T7124-2008 determination of tensile shear strength of adhesive (rigid material to rigid material), the water absorption was measured using 1mm by 50mm sample pieces, and the water absorption was measured by immersing in 0.5mol/L aqueous sodium hydroxide solution for 24 hours, and the water absorption= (mass of sample pieces after immersing-mass of sample pieces before immersing)/mass of sample pieces before immersing, and the results are shown in tables 1-2.
TABLE 1
Figure BDA0004003491660000111
As can be seen from Table 1, the preparation method enables the organosilicon acrylic acid hybrid compound, other monomers containing double bonds, the heat-conducting filler and the like to react through heating free radical initiation, so that the prepared material has better bonding performance, higher heat conductivity, tensile strength and shearing strength, and lower water absorption.
Meanwhile, all the substances are mixed, and solidification can be completed through heating, so that the preparation method is convenient for normal-temperature storage and transportation; in addition, the application is single-component free radical initiated curing, and the curing is completed without adding other substances, so that the preparation method is convenient and quick, and is simple and convenient.
TABLE 2
Figure BDA0004003491660000112
As can be seen from table 2, compared with the single particle size (comparative examples 1-2), the present application, by adjusting the particle size grading of the heat conductive filler, on the one hand, adjusts the heat conductivity of the prepared material, and, on the other hand, by adjusting the grading of the heat conductive filler with different particle sizes, when coated on the solid surface, the compactness is increased, and the tensile strength and the shear strength thereof are enhanced after curing. The material prepared in this application has higher thermal conductivity and tensile strength than the material without the addition of the thermally conductive filler (comparative example 3). Compared with acrylic ester (comparative example 4), the material prepared by the method has higher tensile strength and shear strength, and has extremely low water absorption, thus proving that the water resistance is better. This is probably due to the synergistic effect of the organosilicon acrylic hybrid compound with the free radical initiator and the heat conductive filler, while maintaining low viscosity, better adhesion properties, and improved tensile strength and shear properties.
In conclusion, the preparation method can improve the thermal conductivity, tensile strength and shearing strength of the material by initiating multi-component curing through free radicals, the prepared material has good water resistance, and the material is stable in normal-temperature storage and is single-component direct curing, so that the preparation method is convenient and quick.
While the foregoing is directed to the preferred embodiments of the present invention, it will be appreciated by those skilled in the art that various modifications and adaptations can be made without departing from the principles of the present invention, and such modifications and adaptations are intended to be comprehended within the scope of the present invention.

Claims (10)

1. The organic silicon hybrid composite material is characterized by being prepared from the following raw materials in parts by weight:
Figure FDA0004003491650000011
the structural formula of the organosilicon acrylic acid hybrid compound is as follows:
Figure FDA0004003491650000012
wherein R1 is a compound Containing (CH) 2 ) Or (OCH) 2 CH 2 ) Is a linking group of (2);
r2 is a linking group containing 6 to 30 carbon atoms.
2. The silicone hybrid composite of claim 1, wherein the R2 has the structural formula:
Figure FDA0004003491650000021
3. the silicone hybrid composite of claim 2, wherein the thermally conductive filler is one or more of aluminum oxide, silicon dioxide, zinc oxide, magnesium oxide, aluminum nitride, boron nitride, aluminum hydroxide, silicon nitride, silicon carbide, and calcium carbonate.
4. The silicone hybrid composite according to claim 2, wherein the radical initiator is a cyano compound containing azo groups or an organic peroxide.
5. The silicone hybrid composite of claim 2, wherein the polymerization inhibitor is one or more of hydroquinone, 2, 6-di-tert-butyl-4-cresol (BHT), para-hydroxyanisole, phenothiazine, 4-hydroxy-2, 6-tetramethylpiperidin-1-oxyl, 4- (2-aminoethyl) phenol.
6. The silicone hybrid composite of claim 2, wherein the solvent is one or more of mineral oil, vegetable oil, technical white oil, liquid paraffin, silicone oil.
7. The silicone hybrid composite of claim 2, wherein the other double bond containing monomers are compounds containing one or more carbon-carbon double bond functional groups.
8. The silicone hybrid composite according to claim 7, wherein the other double bond containing monomers are esters of methacrylic acid with alcohols containing C1 to C12, diesters of methacrylic acid with diols containing C1 to C6, triesters of methacrylic acid with triols containing C1 to C6 or oligomers containing methacrylic acid groups.
9. The method for preparing the organic silicon hybrid composite material according to any one of claims 1 to 8, which is characterized in that the organic silicon acrylic acid hybrid compound, the heat conducting filler, the free radical initiator, the polymerization inhibitor, the solvent and other monomers containing double bonds are uniformly mixed and stirred.
10. Use of the silicone hybrid composite according to any one of claims 1 to 8 in the field of thermal management, wherein the silicone hybrid composite according to any one of claims 1 to 8 is applied to a target surface on an extrusion device and is shaped by thermal curing.
CN202211623570.7A 2022-12-16 2022-12-16 Organosilicon hybrid composite material and preparation method and application thereof Pending CN116217804A (en)

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Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110212332A1 (en) * 2008-05-22 2011-09-01 Dic Corporation Aqueous hybrid resin composition, coating preparation containing the same, and laminate therewith
KR20140010914A (en) * 2013-12-23 2014-01-27 에스엠에스주식회사 Optically clear adhesive with high thermal and chemical resistance
CN103666236A (en) * 2013-11-25 2014-03-26 陕西科技大学 VOC (volatile organic compound)-free organosilicone modified water-borne PU (polyurethane) nano hybrid paint and preparation method thereof
CN103709412A (en) * 2013-12-27 2014-04-09 成都硅宝科技股份有限公司 Hybrid organosilicon thermoplastic elastomer and preparation method thereof
CN104017413A (en) * 2014-05-05 2014-09-03 苏州弗克新型建材有限公司 Thermal insulation putty for internal walls and application method thereof
CN107488441A (en) * 2017-09-20 2017-12-19 天津沃尔提莫新材料技术股份有限公司 A kind of liquid metal for conducting heat filler and preparation method
CN110894338A (en) * 2018-09-12 2020-03-20 天津理工大学 Controllable deformation accurate regulation and control composite material based on super-elastic network and preparation method and application thereof
JP6692512B1 (en) * 2018-12-25 2020-05-13 富士高分子工業株式会社 Thermally conductive composition and thermally conductive sheet using the same
US20210070910A1 (en) * 2018-05-16 2021-03-11 Henkel IP & Holding GmbH One-pot process of making silicone-acrylic hybrid pressure sensitive adhesive compositions
CN113039245A (en) * 2018-11-16 2021-06-25 汉高知识产权控股有限责任公司 Dual curable silicone-organic hybrid polymer compositions for liquid optically clear adhesive applications
CN113698855A (en) * 2021-09-09 2021-11-26 西北民族大学 Acrylic acid/organic silicon nano composite modified waterborne polyurethane ship antifouling paint and preparation method thereof
CN114958066A (en) * 2022-06-08 2022-08-30 浙江壁灵宝建材科技有限公司 Waterproof putty and preparation method thereof

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20110212332A1 (en) * 2008-05-22 2011-09-01 Dic Corporation Aqueous hybrid resin composition, coating preparation containing the same, and laminate therewith
CN103666236A (en) * 2013-11-25 2014-03-26 陕西科技大学 VOC (volatile organic compound)-free organosilicone modified water-borne PU (polyurethane) nano hybrid paint and preparation method thereof
KR20140010914A (en) * 2013-12-23 2014-01-27 에스엠에스주식회사 Optically clear adhesive with high thermal and chemical resistance
CN103709412A (en) * 2013-12-27 2014-04-09 成都硅宝科技股份有限公司 Hybrid organosilicon thermoplastic elastomer and preparation method thereof
CN104017413A (en) * 2014-05-05 2014-09-03 苏州弗克新型建材有限公司 Thermal insulation putty for internal walls and application method thereof
CN107488441A (en) * 2017-09-20 2017-12-19 天津沃尔提莫新材料技术股份有限公司 A kind of liquid metal for conducting heat filler and preparation method
US20210070910A1 (en) * 2018-05-16 2021-03-11 Henkel IP & Holding GmbH One-pot process of making silicone-acrylic hybrid pressure sensitive adhesive compositions
CN110894338A (en) * 2018-09-12 2020-03-20 天津理工大学 Controllable deformation accurate regulation and control composite material based on super-elastic network and preparation method and application thereof
CN113039245A (en) * 2018-11-16 2021-06-25 汉高知识产权控股有限责任公司 Dual curable silicone-organic hybrid polymer compositions for liquid optically clear adhesive applications
JP6692512B1 (en) * 2018-12-25 2020-05-13 富士高分子工業株式会社 Thermally conductive composition and thermally conductive sheet using the same
CN113698855A (en) * 2021-09-09 2021-11-26 西北民族大学 Acrylic acid/organic silicon nano composite modified waterborne polyurethane ship antifouling paint and preparation method thereof
CN114958066A (en) * 2022-06-08 2022-08-30 浙江壁灵宝建材科技有限公司 Waterproof putty and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
侯志成;姚伯龙;沈锋;韩兵;: "UV-潮气双重固化有机硅杂化聚氨酯的制备与性能研究", 化工新型材料, no. 09, 15 September 2012 (2012-09-15), pages 41 - 48 *

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