CN116144315A - Dealcoholized organosilicon sealant and preparation method thereof - Google Patents

Dealcoholized organosilicon sealant and preparation method thereof Download PDF

Info

Publication number
CN116144315A
CN116144315A CN202211584794.1A CN202211584794A CN116144315A CN 116144315 A CN116144315 A CN 116144315A CN 202211584794 A CN202211584794 A CN 202211584794A CN 116144315 A CN116144315 A CN 116144315A
Authority
CN
China
Prior art keywords
parts
dealcoholized
coupling agent
trimethoxysilane
alpha
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.)
Granted
Application number
CN202211584794.1A
Other languages
Chinese (zh)
Other versions
CN116144315B (en
Inventor
何睿
刘畅
喻学锋
李书兵
黄前华
胡瑞
胡莉
孙刚
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.)
Hubei Xingrui Silicon Material Co Ltd
Original Assignee
Hubei Xingrui Silicon Material 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 Hubei Xingrui Silicon Material Co Ltd filed Critical Hubei Xingrui Silicon Material Co Ltd
Priority to CN202211584794.1A priority Critical patent/CN116144315B/en
Publication of CN116144315A publication Critical patent/CN116144315A/en
Application granted granted Critical
Publication of CN116144315B publication Critical patent/CN116144315B/en
Active legal-status Critical Current
Anticipated expiration legal-status Critical

Links

Images

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
    • C09J183/04—Polysiloxanes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/04—Non-macromolecular additives inorganic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/02—Non-macromolecular additives
    • C09J11/06—Non-macromolecular additives organic
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
    • C09J11/08—Macromolecular additives
    • 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
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/011—Nanostructured additives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2201/00—Properties
    • C08L2201/08—Stabilised against heat, light or radiation or oxydation

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Sealing Material Composition (AREA)

Abstract

The application relates to the technical field of adhesives, in particular to dealcoholized organosilicon sealant and a preparation method thereof. The organosilicon sealant is prepared from alpha, omega-dihydroxy polydimethylsiloxane, a filler, a plasticizer, a cross-linking agent, a coupling agent, a catalyst and a stabilizer; wherein the coupling agent has a plurality of alkoxy groups which undergo a condensation reaction with the hydroxyl groups of the alpha, omega-dihydroxydimethicone. The raw material combination of the dealcoholized organosilicon sealant can improve the storage stability of the sealant without modifying alpha, omega-dihydroxy polydimethylsiloxane, and the storage stability can reach more than 12 months.

Description

Dealcoholized organosilicon sealant and preparation method thereof
Technical Field
The application relates to the technical field of adhesives, in particular to dealcoholized organosilicon sealant and a preparation method thereof.
Background
The dealcoholized organosilicon sealant has the advantages of no corrosion and no pungent smell to the bonding base material, and is widely applied to the photovoltaic industry and the electronic and electric industry. In the storage process of the dealcoholized organosilicon sealant, trace moisture and free alcohol contained in the dealcoholized organosilicon sealant react with polysiloxane in the presence of an organometallic catalyst in a chain cutting and balancing way to form a short chain and non-crosslinking functional (CH) 3 O)(CH 3 ) 2 SiO 1/2 End groups and the like, and the curing performance and physical properties of the product gradually decline or even disappear with the extension of storage time. In the prior art, the following two modes are mainly adopted to improve the storage stability of the dealcoholized organosilicon sealant: 1. alkoxy end capping modification is carried out on the base polymer alpha, omega-dihydroxy polydimethylsiloxane; 2. as the stabilizer, nitrogen silane, molecular sieve, calcium chloride, etc. are generally used. The first way, although it can better solve the problem of storage stability, requires additional process steps, resulting in increased cost; the second approach has limited effectiveness and can result in other performance degradation.
Based on the above analysis, it is important to provide a raw material combination that improves the storage stability of dealcoholized silicone sealants without adding process steps.
Disclosure of Invention
The embodiment of the application provides a dealcoholized organic silicon sealant, which aims to solve the problem of improving the storage stability of the organic silicon sealant by adding process steps in the related art.
In a first aspect, the present application provides a dealcoholized silicone sealant prepared from an α, ω -dihydroxypolydimethylsiloxane, a filler, a plasticizer, a crosslinking agent, a coupling agent, a catalyst, and a stabilizer; wherein the coupling agent has an alkoxy group that undergoes a condensation reaction with a hydroxyl group of the α, ω -dihydroxydimethicone.
In some embodiments, the mass parts of the raw materials are as follows: 100 parts of alpha, omega-dihydroxyl polydimethylsiloxane, 60-150 parts of filler, 5-40 parts of plasticizer, 2-15 parts of cross-linking agent, 0.5-8 parts of coupling agent, 1-10 parts of catalyst and 0.1-5 parts of stabilizer.
In some embodiments, the α, ω -dihydroxypolydimethylsiloxane has the formula:
Figure BDA0003992450900000011
wherein n is a positive integer which enables the kinematic viscosity of alpha, omega-dihydroxypolydimethylsiloxane to be 1000-200000 mPa.S at 25 ℃; r is methyl, phenyl or vinyl.
In some preferred embodiments, R is methyl.
In some preferred embodiments, the alpha, omega-dihydroxy polydimethylsiloxane has an kinematic viscosity at 25℃of 5000-80000 mPa.S.
In some embodiments, the coupling agent comprises an alpha-coupling agent trimer having the structural formula:
Figure BDA0003992450900000021
wherein R is 1 、R 2 、R 3 Each independently is C1-C4 alkyl, R 1 、R 2 、R 3 May be the same group or may be different groups. The functional group of the alpha-coupling agent trimer is separated from the silicon atom by only one carbon atom, and the functional group and the silicon atom are close to each other, so that the electron effect on the functional group is more easily transferred to the silicon atom, the alkoxy group directly connected with the silicon atom becomes abnormally active, the condensation reaction with the silicon hydroxyl group is easily carried out to remove alcohol, the content of the silicon hydroxyl group in the system is reduced, and the storage stability of the sealant is improvedSex; in addition, the molecular structure contains a special nitrogen-containing heterocyclic structure, so that the moisture-heat resistant adhesion of the sealant to various base materials such as aluminum, copper, polycarbonate, PPO, ABS and the like can be improved.
In some preferred embodiments, R 1 、R 2 、R 3 Each independently is methyl or ethyl.
In some embodiments, the coupling agent further comprises a mixture of one or more of aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N- (β -aminoethyl) - γ -aminopropyl trimethoxysilane, γ -acyloxypropyl trimethoxysilane, γ -glycidoxypropyl trimethoxysilane, γ -mercaptopropyl trimethoxysilane, isocyanatopropyl trimethoxysilane, γ - (2, 3-epoxypropoxy) propyl trimethoxysilane, N-diethyl-3-aminopropyl trimethoxysilane, bis- [3- (methoxysilicon) -propyl ] -amine, and 2- (3, 4-epoxycyclohexane) ethyl trimethoxysilane.
In some preferred embodiments, the coupling agent comprises aminopropyl triethoxysilane, gamma- (2, 3-glycidoxy) propyl trimethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyl trimethoxysilane, or a corresponding hydrolyzed copolymer.
In some embodiments, the amount of the α -coupling agent trimer is 20% to 80% of the total mass of the coupling agent.
In some embodiments, the plasticizer comprises a hydroxyl-terminated polybutadiene and a polydimethylsiloxane having an kinematic viscosity at 25 ℃ of 100-1000 mPa-S. The viscosity of the hydroxyl-terminated polybutadiene is 100-1000 mPa.S, the molecules of the polybutadiene are of a directional three-dimensional structure, the periphery of the molecular structure is terminated by active hydroxyl groups, and the polybutadiene can form chemical bonding with alpha, omega-dihydroxy polydimethylsiloxane, so that the mechanical property of the sealant is improved; the polydibutene has lower moisture vapor transmission rate, so that the high-temperature and high-humidity resistance of the sealant can be effectively improved after the polydibutene is completely cured.
In some embodiments, the hydroxyl-terminated polybutadiene and polydimethylsiloxane are mixed in a mass ratio of 1:5-5:1.
in some embodiments, the filler is a mixture of one or more of nano calcium carbonate, micro silica powder, fumed silica, light calcium carbonate, and heavy calcium carbonate; the nano calcium carbonate is active nano calcium carbonate which is surface treated by stearic acid, and the average grain diameter is 50-100nm.
In some embodiments, the cross-linking agent is one or more of methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, isopropyltrimethoxysilane, isopropyltriethoxysilane, phenyltrimethoxyphenyltriethoxysilane, methyl orthosilicate, ethyl orthosilicate.
In some embodiments, the catalyst is a mixture of one or more of n-butyl titanate, tetraisobutyl titanate, n-propyl titanate, tetraisopropyl titanate, t-butyl titanate, and a titanium complex of ethyl acetoacetate.
In some embodiments, the stabilizer is one or more of hexamethyldisilazane, hexamethylcyclotrisilazane, isocyanatopropyl trimethoxysilane, divinyl tetramethoxydisilazane, calcium chloride, magnesium chloride, zeolite, molecular sieves.
In some preferred embodiments, the stabilizer is divinyl tetramethoxy disilazane or hexamethyldisilazane.
In a second aspect, an embodiment of the present application further provides a method for preparing the dealcoholized silicone sealant, including the following steps:
mixing alpha, omega-dihydroxy polydimethylsiloxane, plasticizer and filler, heating and vacuumizing to obtain a mixed base material;
and sequentially adding a cross-linking agent, a coupling agent, a catalyst and a stabilizer into the mixed base material, and vacuumizing to obtain the dealcoholized organosilicon sealant.
The beneficial effects that technical scheme that this application provided brought include: the coupling agent in the raw material combination of the dealcoholized organosilicon sealant provided by the application has the advantages that the alkoxy contained in the coupling agent can be subjected to condensation reaction with the silicon hydroxyl groups of the alpha, omega-dihydroxy polydimethylsiloxane to dealcoholize, the silicon hydroxyl content in the system is reduced, the reaction of free alcohol and polysiloxane is effectively avoided, the improvement of the storage stability of the sealant can be realized without modifying the alpha, omega-dihydroxy polydimethylsiloxane, and the storage stability can reach more than 12 months.
Drawings
In order to more clearly illustrate the technical solutions of the embodiments of the present application, the drawings that are needed in the description of the embodiments will be briefly introduced below, and it is obvious that the drawings in the following description are only some embodiments of the present application, and that other drawings may be obtained according to these drawings without inventive effort for a person skilled in the art.
Fig. 1 is a schematic flow chart of a preparation method of a dealcoholized silicone sealant according to an embodiment of the present application.
Detailed Description
For the purposes of making the objects, technical solutions and advantages of the embodiments of the present application more clear, the technical solutions of the embodiments of the present application will be clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is apparent that the described embodiments are some embodiments of the present application, but not all embodiments. All other embodiments, which can be made by one of ordinary skill in the art without undue burden from the present disclosure, are within the scope of the present application based on the embodiments herein.
Embodiments of the present application provide a dealcoholized silicone sealant, which can solve the problems of the related art that the storage stability of the silicone sealant is improved by adding process steps.
Referring to fig. 1, the preparation method of the dealcoholized organosilicon sealant provided in the embodiment of the application includes the following steps:
step S101, adding 100 parts of alpha, omega-dihydroxyl polydimethylsiloxane, 5-40 parts of plasticizer and 60-150 parts of filler into a stirring kettle according to parts by weight, stirring and dehydrating for 2-4 hours at the temperature of 120-150 ℃ under the condition of vacuumizing, and cooling to obtain a mixed base material;
step S102, sequentially adding 2-15 parts of cross-linking agent, 0.5-8 parts of coupling agent, 1-10 parts of catalyst and 0.1-5 parts of stabilizer into the mixed base material according to the parts by mass, and vacuumizing to obtain the dealcoholized organosilicon sealant.
Wherein, the structural formula of the alpha, omega-dihydroxy polydimethylsiloxane is as follows:
Figure BDA0003992450900000041
wherein R is methyl, phenyl or vinyl.
The coupling agent composition comprises an alpha-coupling agent trimer, and the structural formula of the alpha-coupling agent trimer is shown as the formula (I):
formula (I):
Figure BDA0003992450900000042
wherein R is 1 、R 2 、R 3 Each independently is C1-C4 alkyl, R 1 、R 2 、R 3 May be the same group or may be different groups.
The alpha-coupling agent trimer is prepared by the following process: adding an alpha halogenated silane coupling agent, cyanate and nickel complex into a solvent, stirring uniformly, completely dissolving the mixture, heating the mixture to 100-140 ℃, reacting the mixture for 3-5 hours, filtering the obtained solution, and distilling the solution under reduced pressure to obtain alpha-isocyanate methylsilane; adding alpha-isocyanate methylsilane into a reaction kettle, adding a catalyst in the presence of a solvent, then reacting for 3-5 hours at 50-80 ℃, then adding benzoyl chloride, and continuing to react for 0.5-1 hour to obtain an alpha-coupling agent trimer; the solvent used in the preparation process is methyl isobutyl ketone, N-dimethylformamide or N-butyl acetate; the catalyst used is an organophosphorus catalyst, an organic amine catalyst or an organic base catalyst; the cyanate is potassium cyanate or sodium cyanate; the structural formula of the alpha halogenated silane coupling agent is as follows:
Figure BDA0003992450900000043
the coupling agent also includes a mixture of one or more of aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N- (beta-aminoethyl) -gamma-aminopropyl trimethoxysilane, gamma-acyloxypropyl trimethoxysilane, gamma-glycidoxypropyl trimethoxysilane, gamma-mercaptopropyl trimethoxysilane, isocyanatopropyl trimethoxysilane, gamma- (2, 3-glycidoxy) propyl trimethoxysilane, N-diethyl-3-aminopropyl trimethoxysilane, bis- [3- (methoxysilyl) -propyl ] -amine, and 2- (3, 4-epoxycyclohexane) ethyl trimethoxysilane.
Plasticizers include hydroxy-terminated polybutadiene and polydimethylsiloxane.
The dealcoholized silicone sealants provided herein and the preparation method thereof are described in detail below with reference to examples and comparative examples.
Example 1
Embodiment 1 provides a preparation method of dealcoholized organosilicon sealant, which comprises the following steps:
(1) Adding 100 parts by mass of alpha, omega-dihydroxyl polydimethylsiloxane with the viscosity of 20000 mPa.S at 25 ℃, 100 parts by mass of nano calcium carbonate, 15 parts by mass of polydimethylsiloxane with the viscosity of 300 mPa.S at 25 ℃, 10 parts by mass of hydroxyl-terminated liquid polybutadiene with the viscosity of 400 mPa.S at 25 ℃ and 10 parts by mass of fumed silica into a vacuum kneader, dehydrating, blending and kneading for 3 hours under the conditions of the temperature of 120 ℃ and the vacuum degree of 0.095MPa, and cooling to obtain a mixed base material;
(2) At room temperature, adding 7 parts of methyltrimethoxysilane, 3 parts of vinyltrimethoxysilane, 1 part of aminopropyl triethoxysilane, 2 parts of gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane and 5 parts of titanium complex of ethyl acetoacetate into a high-speed dispersion stirrer or a planetary stirrer with the mixed base material, stirring for 30min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, vacuumizing, sequentially adding 4 parts of alpha-coupling agent trimer and 0.5 part of hexamethyldisilazane, stirring for 10min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, and vacuumizing to obtain the single-component dealcoholized organosilicon sealant.
In example 1, the nano calcium carbonate used was activated nano calcium carbonate treated with stearic acid, and the fumed silica used was surface-treated with hexamethyldisilazaneFumed silica having a specific surface area of 160m 2 /g。
In example 1, the alpha-coupling agent trimer used has the structural formula (I) wherein R 1 Is methyl, R 2 And R is 3 Is ethyl.
Comparative example 1
Comparative example 1 provides a method for preparing dealcoholized silicone sealant, and comparative example 1 provides a method differing from example 1 only in that: comparative example 1 no alpha-coupling agent trimer was added during the preparation of the silicone sealant; the rest of the procedure is substantially the same as in example 1.
Comparative example 2
Comparative example 2 provides a method for preparing dealcoholized silicone sealant, and comparative example 2 provides a method differing from example 1 only in that: comparative example 2 no hydroxy-terminated liquid polybutadiene was added during the preparation of the silicone sealant; the rest of the procedure is substantially the same as in example 1.
Example 2
Embodiment 2 provides a preparation method of dealcoholized organosilicon sealant, which comprises the following steps:
(1) Adding 100 parts by mass of alpha, omega-dihydroxyl polydimethylsiloxane with the viscosity of 50000 mPa.S at 25 ℃, 120 parts by mass of nano calcium carbonate, 5 parts by mass of polydimethylsiloxane with the viscosity of 200 mPa.S at 25 ℃, 10 parts by mass of hydroxyl-terminated liquid polybutadiene with the viscosity of 400 mPa.S at 25 ℃ and 10 parts by mass of fumed silica into a vacuum kneader, dehydrating, blending and kneading for 3 hours at 130 ℃ and the vacuum degree of 0.095MPa, and cooling to obtain a mixed base material;
(2) At room temperature, adding 5 parts of methyltrimethoxysilane, 3 parts of vinyltriethoxysilane, 2 parts of aminopropyl trimethoxysilane, 2 parts of gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane and 4 parts of titanium complex of ethyl acetoacetate into a high-speed dispersion stirrer or a planetary stirrer with the mixed base material, stirring for 30min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, vacuumizing, sequentially adding 2 parts of alpha-coupling agent trimer and 3 parts of hexamethyl-cyclotrisilazane, stirring for 10min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, and vacuumizing to obtain the single-component dealcoholized organic silicon sealant.
In example 2, the nano calcium carbonate used was stearic acid-treated active nano calcium carbonate, the fumed silica used was hexamethyldisilazane surface-treated fumed silica, and the specific surface area was 160m 2 /g。
In example 2, the alpha-coupling agent trimer used has the formula (I) wherein R 1 Is methyl, R 2 Is ethyl, R 3 Is butyl.
Example 3
Embodiment 3 provides a preparation method of dealcoholized organosilicon sealant, which comprises the following steps:
(1) Adding 100 parts by mass of alpha, omega-dihydroxyl polydimethylsiloxane with the viscosity of 20000 mPa.S at 25 ℃, 80 parts by mass of nano calcium carbonate, 15 parts by mass of polydimethylsiloxane with the viscosity of 600 mPa.S at 25 ℃, 15 parts by mass of hydroxyl-terminated liquid polybutadiene with the viscosity of 600 mPa.S at 25 ℃ and 10 parts by mass of silicon micropowder into a vacuum kneader, dehydrating, blending and kneading for 3h under the conditions of the temperature of 140 ℃ and the vacuum degree of 0.095MPa, and cooling to obtain a mixed base material;
(2) According to the mass parts, 4 parts of isopropyl triethoxysilane, 3 parts of isopropyl trimethoxysilane, 0.5 part of aminopropyl triethoxysilane, 1 part of gamma-mercaptopropyl trimethoxysilane and 3 parts of n-butyl titanate are added into a high-speed dispersion stirrer or a planetary stirrer with the mixed base materials at room temperature, stirring is carried out for 30min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, then vacuumizing is carried out, then 1 part of alpha-coupling agent trimer and 1 part of divinyl tetramethoxy disilazane are sequentially added, stirring is carried out for 10min under the conditions of vacuum degree of-0.095 to-0.1 MPa and rotating speed of 80rpm, and then vacuumizing is carried out, so that the single-component dealcoholized organic silicon sealant is obtained.
In example 3, the nano calcium carbonate used was stearic acid treated activated nano calcium carbonate.
In example 3, the alpha-coupling agent trimer used has the formula (I) wherein R 1 And R is 2 Is ethyl, R 3 Is butyl.
Example 4
Example 4 differs from example 1 only in that: no aminopropyl triethoxysilane and gamma- (2, 3-epoxypropoxy) propyl trimethoxysilane are added in the process of preparing the organosilicon sealant; the remainder was substantially the same as in example 1.
The silicone sealants prepared in examples 1 to 4 and comparative examples 1 to 2 were subjected to performance test, and the results are shown in Table 1.
Table 1: performance comparison of the Silicone sealants prepared in examples 1-4 and comparative examples 1-2
Figure BDA0003992450900000071
Note that: the heat storage aging condition is 70 ℃ multiplied by 7d, and the double 85 environmental aging condition is as follows: the temperature is 85+/-2 ℃ and the humidity is 85+/-5%
From the results of examples 1-4 and comparative examples 1-2, it can be seen that the heat storage aging performance and dual 85 environmental aging of the sealants prepared in comparative example 1 without the addition of the α -coupling agent trimer were significantly lower than those prepared in example 1; the mechanical properties of the sealant prepared without polybutadiene in comparative example 2 were significantly lower than those of the sealant prepared in example 1.
In the description of the present specification, reference to the terms "one embodiment/manner," "some embodiments/manner," "example," "a particular example," or "some examples," etc., means that a particular feature, structure, material, or characteristic described in connection with the embodiment/manner or example is included in at least one embodiment/manner or example of the present application. In this specification, the schematic representations of the above terms are not necessarily for the same embodiment/manner or example. Furthermore, the particular features, structures, materials, or characteristics described may be combined in any suitable manner in any one or more embodiments/modes or examples. Furthermore, the various embodiments/modes or examples described in this specification and the features of the various embodiments/modes or examples can be combined and combined by persons skilled in the art without contradiction.
It should be noted that in this application, relational terms such as "first" and "second" and the like are used solely to distinguish one entity or action from another entity or action without necessarily requiring or implying any actual such relationship or order between such entities or actions. Moreover, the terms "comprises," "comprising," or any other variation thereof, are intended to cover a non-exclusive inclusion, such that a process, method, article, or apparatus that comprises a list of elements does not include only those elements but may include other elements not expressly listed or inherent to such process, method, article, or apparatus. Without further limitation, an element defined by the phrase "comprising one … …" does not exclude the presence of other like elements in a process, method, article, or apparatus that comprises the element. In the present application, the meaning of "plurality" means at least two, for example, two, three, etc., unless explicitly specified otherwise.
The foregoing is merely a specific embodiment of the application to enable one skilled in the art to understand or practice the application. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the application. Thus, the present application is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.

Claims (10)

1. The dealcoholized organosilicon sealant is characterized in that the dealcoholized organosilicon sealant is prepared from alpha, omega-dihydroxy polydimethylsiloxane, a filler, a plasticizer, a cross-linking agent, a coupling agent, a catalyst and a stabilizer; wherein the coupling agent has a plurality of alkoxy groups which undergo a condensation reaction with the hydroxyl groups of the alpha, omega-dihydroxydimethicone.
2. The dealcoholized silicone sealant according to claim 1, wherein the coupling agent comprises an α -coupling agent trimer having the structural formula:
Figure DEST_PATH_IMAGE002
wherein R is 1 、R 2 、R 3 Each independently is a C1-C4 alkyl group.
3. The dealcoholized silicone sealant according to claim 2, wherein the coupling agent further comprises a mixture of one or more of aminopropyl trimethoxysilane, aminopropyl triethoxysilane, N- (β -aminoethyl) - γ -aminopropyl trimethoxysilane, γ -methacryloxypropyl trimethoxysilane, γ -glycidoxypropyl trimethoxysilane, γ -mercaptopropyl trimethoxysilane, isocyanatopropyl trimethoxysilane, γ - (2, 3-epoxypropoxy) propyl trimethoxysilane, N-diethyl-3-aminopropyl trimethoxysilane, bis- [3- (methoxysilicon) -propyl ] -amine, and 2- (3, 4-epoxycyclohexane) ethyl trimethoxysilane.
4. The dealcoholized silicone sealant according to claim 2, wherein the mass amount of the α -coupling agent trimer is 20% to 80% of the total mass of the coupling agent.
5. The dealcoholized silicone sealant according to claim 1, wherein the plasticizer comprises hydroxyl-terminated polybutadiene and polydimethylsiloxane.
6. The dealcoholized silicone sealant according to claim 5, wherein the mass ratio of the hydroxyl-terminated polybutadiene to the polydimethylsiloxane is 1:5-5:1.
7. the dealcoholized silicone sealant according to claim 1, wherein the filler is a mixture of one or more of nano calcium carbonate, fine silica powder, fumed silica, light calcium carbonate and heavy calcium carbonate.
8. The dealcoholized silicone sealant according to claim 1, wherein the cross-linking agent is one or more of methyltrimethoxysilane, methyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, isopropyltrimethoxysilane, isopropyltriethoxysilane, phenyltrimethoxyphenyltriethoxysilane, methyl orthosilicate, ethyl orthosilicate.
9. The dealcoholized organosilicon sealant according to claim 1, wherein the weight parts of the raw materials are: 100 parts of alpha, omega-dihydroxyl polydimethylsiloxane, 60-150 parts of filler, 5-40 parts of plasticizer, 2-15 parts of cross-linking agent, 0.5-8 parts of coupling agent, 1-10 parts of catalyst and 0.1-5 parts of stabilizer.
10. The method for preparing the dealcoholized organosilicon sealant according to any one of claims 1 to 9, comprising the steps of:
mixing alpha, omega-dihydroxy polydimethylsiloxane, plasticizer and filler, heating and vacuumizing to obtain a mixed base material;
and sequentially adding a cross-linking agent, a coupling agent, a catalyst and a stabilizer into the mixed base material, and vacuumizing to obtain the dealcoholized organosilicon sealant.
CN202211584794.1A 2022-12-11 2022-12-11 Dealcoholized organosilicon sealant and preparation method thereof Active CN116144315B (en)

Priority Applications (1)

Application Number Priority Date Filing Date Title
CN202211584794.1A CN116144315B (en) 2022-12-11 2022-12-11 Dealcoholized organosilicon sealant and preparation method thereof

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
CN202211584794.1A CN116144315B (en) 2022-12-11 2022-12-11 Dealcoholized organosilicon sealant and preparation method thereof

Publications (2)

Publication Number Publication Date
CN116144315A true CN116144315A (en) 2023-05-23
CN116144315B CN116144315B (en) 2024-10-18

Family

ID=86359114

Family Applications (1)

Application Number Title Priority Date Filing Date
CN202211584794.1A Active CN116144315B (en) 2022-12-11 2022-12-11 Dealcoholized organosilicon sealant and preparation method thereof

Country Status (1)

Country Link
CN (1) CN116144315B (en)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117050718A (en) * 2023-07-17 2023-11-14 江苏明昊新材料科技股份有限公司 Double-component dealcoholized sealant for photovoltaic frame and preparation method thereof

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833504A (en) * 2017-02-10 2017-06-13 深圳市森日有机硅材料股份有限公司 A kind of heat conduction single-component dealcoholization-type RTV fluid sealants and preparation method thereof
CN106957631A (en) * 2017-05-11 2017-07-18 杭州之江有机硅化工有限公司 A kind of dealcoholized silicone rubber sealant
CN109722216A (en) * 2018-12-29 2019-05-07 江苏创景科技有限公司 A kind of Silante terminated liquid polybutadiene modified organic silicon sealant and preparation method thereof
CN112574712A (en) * 2020-12-11 2021-03-30 绵阳惠利电子材料有限公司 Bi-component room temperature vulcanized silicone rubber composition for sensor and preparation method thereof

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN106833504A (en) * 2017-02-10 2017-06-13 深圳市森日有机硅材料股份有限公司 A kind of heat conduction single-component dealcoholization-type RTV fluid sealants and preparation method thereof
CN106957631A (en) * 2017-05-11 2017-07-18 杭州之江有机硅化工有限公司 A kind of dealcoholized silicone rubber sealant
CN109722216A (en) * 2018-12-29 2019-05-07 江苏创景科技有限公司 A kind of Silante terminated liquid polybutadiene modified organic silicon sealant and preparation method thereof
CN112574712A (en) * 2020-12-11 2021-03-30 绵阳惠利电子材料有限公司 Bi-component room temperature vulcanized silicone rubber composition for sensor and preparation method thereof

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
段久芳编著: "《天然高分子材料》", vol. 1, 30 September 2016, 华中科技大学出版社, pages: 308 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN117050718A (en) * 2023-07-17 2023-11-14 江苏明昊新材料科技股份有限公司 Double-component dealcoholized sealant for photovoltaic frame and preparation method thereof

Also Published As

Publication number Publication date
CN116144315B (en) 2024-10-18

Similar Documents

Publication Publication Date Title
CN110305621B (en) Dealcoholized room-temperature curing organosilicon sealant and preparation method thereof
TWI617642B (en) Moisture-curable hot melt silicone adhesive compositions including an alkoxy-functional siloxane reactive resin
CN110003842B (en) Single-component dealcoholized room temperature vulcanized organopolysiloxane composition
US5468826A (en) Adhesion promoting additives and curable organosiloxane compositions containing same
EP3645643A1 (en) Dual cure organopolysiloxane composition
EP0178751B1 (en) Silicone elastomers with good adhesion
CN110577747B (en) Room temperature vulcanized fluorosilicone rubber and preparation method thereof
CN105001422B (en) A kind of addition-type silicon rubber tackifier and preparation method thereof and addition-type silicon rubber
CN111394052B (en) Dealcoholized condensed type double-component room temperature vulcanized silicone rubber and preparation method thereof
CN116144315B (en) Dealcoholized organosilicon sealant and preparation method thereof
CN101787256A (en) Addition type silicone adhesive composition and preparation method thereof
CN109593510A (en) Alkoxy end-capped organosilicon polymer, preparation method and single-component de-alcoholized organosilicon sealant
CN111499877A (en) Preparation method of organic silicon modified epoxy resin
CN110387128B (en) Self-adhesive single-component addition type silicone rubber and preparation method thereof
CN112662370B (en) Single-component dealcoholized silicone sealant and preparation method thereof
CN109181623B (en) Silicone sealant for fast curing photovoltaic module and preparation method thereof
CN114262550A (en) Silane modified acrylic resin, synthetic method and primer for silicone rubber
JPH10237174A (en) Silylated polymethylsilsesquioxane
CN114316897A (en) Silicone sealant and preparation method thereof
CN112812733B (en) Low-modulus high-elongation transparent pouring sealant composition and preparation method thereof
CN112210341B (en) Double-vulcanization system building sealant and preparation method thereof
CN114656643B (en) Phenyl-containing cross-linking agent, high-temperature-resistant silicon rubber for bonding and sealing and preparation method thereof
CN104829642B (en) Silane compound and preparation method thereof and translucent dealcoholized cold curing silicon rubber and preparation method thereof
CN113480969A (en) Preparation method of single-component transparent alcohol type room temperature vulcanized silicone sealant
CN113444123A (en) Ultraviolet absorbent and preparation method and application thereof

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
GR01 Patent grant