CN110256956A - A kind of silicon rubber silane coupling agent and preparation method thereof - Google Patents
A kind of silicon rubber silane coupling agent and preparation method thereof Download PDFInfo
- Publication number
- CN110256956A CN110256956A CN201910588943.3A CN201910588943A CN110256956A CN 110256956 A CN110256956 A CN 110256956A CN 201910588943 A CN201910588943 A CN 201910588943A CN 110256956 A CN110256956 A CN 110256956A
- Authority
- CN
- China
- Prior art keywords
- coupling agent
- silane coupling
- silicon rubber
- silane
- acid
- 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
Links
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular 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
- C09J5/00—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers
- C09J5/02—Adhesive processes in general; Adhesive processes not provided for elsewhere, e.g. relating to primers involving pretreatment of the surfaces to be joined
-
- 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
- C09J2400/00—Presence of inorganic and organic materials
- C09J2400/10—Presence of inorganic materials
- C09J2400/14—Glass
- C09J2400/143—Glass in the substrate
-
- 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
- C09J2483/00—Presence of polysiloxane
- C09J2483/006—Presence of polysiloxane in the substrate
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The present invention relates to high molecule sealing materials fields more particularly to a kind of silicon rubber silane coupling agent and preparation method thereof.Silicon rubber silane coupling agent includes: 5~20 parts of methoxyl group silicone resin according to parts by weight；1~10 part of cohesive promoting agent；1~5 part of esters of silicon acis；1~5 part of silane coupling agent；1~5 part of catalyst；60~90 parts of solvent；The cohesive promoting agent is made by epoxy silane and secondary amine silane reaction；The silane coupling agent is selected from vinyl silane tri-butyl peroxy and/or double-[γ-(triethoxysilicane) propyl] tetrasulfide.Silicon rubber silane coupling agent provided by the invention can not only improve single-component silicon rubber in the cementability of LOW-E glass surface, moreover it is possible to improve two-component silicone rubber in the cementability of LOW-E glass surface.The cohesional failure that experiment shows that the silicon rubber either cooperates one-component silicone adhesive or cooperation two-component silicone adhesive to use with silane coupling agent is attained by 85% or even 100%.
Description
Technical field
The present invention relates to high molecule sealing materials fields more particularly to a kind of silicon rubber silane coupling agent and preparation method thereof.
Background technique
The heat loss of outer door glass is the major part of building energy consumption, accounts for 50% of building energy consumption or more.It is related
Research data shows that the heat transfer of interior surfaces of glass based on radiating, accounts for 58%, it means that subtract from the performance for changing glass
The loss of few thermal energy, most efficient method are to inhibit the radiation of its inner surface.The radiance of common float glass is up to 0.84, when
After plating one layer of low radiation film based on silver, radiance can be down to 0.15 or less.Therefore, with Low-E glass manufacture
Building window can substantially reduce indoor heat caused by due to radiation to outdoor transmitting, reach ideal energy-saving effect.
Another significant benefit brought by the reduction of indoor thermal loss is environmental protection.Cold season, because of constructure heating
Caused CO2、SO2The discharge of equal pernicious gases is important pollution sources.If using Low-E glass, due to the drop of heat loss
It is low, it can be greatly decreased because of fuel consumed by heating, to reduce the discharge of pernicious gas.
Heat through glass be it is two-way, heat can be transmitted to outdoor by interior, and vice versa, and be simultaneously into
Capable, only transmit the problem of heat difference.When winter, indoor temperature is higher than outdoor, it is desirable that heat preservation.Summer Indoor Temperature
It spends lower than outdoor, it is desirable that glass can be heat-insulated, and what exactly outdoor heat was few as far as possible is transmitted to interior.Low-E glass can be realized
The requirement in winter and summer can be kept the temperature but also heat-insulated, play the effect of environmentally friendly low-carbon.
Low-E glass also has good optical property, and the reflectivity of visible light can be effectively reduced.Due to These characteristics,
Low-E glass has been widely used in developed country.
However Low-E glass is the membrane system product that surface plates multiple layer metal or other compounds composition.Due to depositing for film
Causing usual silicone rubber to substantially reduce in its surface adhesive property, interface peel often occurring, is being loosened very so as to cause glass
To falling.
To solve the above-mentioned problems, it is badly in need of developing a kind of silane coupling agent, improves silicon rubber in the cementability of LOW-E glass surface.
Summary of the invention
In view of this, the technical problem to be solved in the present invention is that providing a kind of silicon rubber silane coupling agent and its preparation side
Method, silicon rubber silane coupling agent provided by the invention can not only improve single-component silicon rubber in the cementability of LOW-E glass surface, also
Two-component silicone rubber can be improved in the cementability of LOW-E glass surface.
The present invention provides a kind of silicon rubber silane coupling agents, include: according to parts by weight
The cohesive promoting agent is made by epoxy silane and secondary amine silane reaction；
The silane coupling agent is selected from vinyl silane tri-butyl peroxy and/or double-[γ-(triethoxysilicane) propyl]
Tetrasulfide.
Preferably, the methoxyl group silicone resin has the structure as shown in formula (I):
In formula (I), R1For hydrogen or methyl；R2For methyl or ethyl；R3For methyl.
Preferably, the number-average molecular weight of the methoxyl group silicone resin is 500~5000.
Preferably, the epoxy silane is selected from γ-glycidyl ether oxygen propyl trimethoxy silicane, 3- (2,3- epoxies third
Oxygen) hydroxypropyl methyl diethoxy silane, 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl dimethoxysilane, γ-glycidyl ether oxygen
Propyl-triethoxysilicane, β-(3,4 epoxycyclohexyl)-ethyl triethoxysilane and β-(3,4 epoxycyclohexyl)-ethyl three
One or more of methoxy silane；
The secondary amino silanes are selected from N- (normal-butyl)-γ-aminopropyltrimethoxysilane, N- cyclohexyl-γ-aminopropyl
Methyl dimethoxysilane, bis- (3- trimethoxy-silylpropyl) amine, double-(γ-trimethoxy silicon propyl) amine, bis- (3-
Triethoxysilylpropyl) one or more of amine and N- phenyl-γ-aminopropyltrimethoxysilane.
Preferably, the esters of silicon acis is selected from methyl orthosilicate and/or ethyl orthosilicate.
Preferably, the catalyst is selected from one or more of titanate esters, zirconate and Aluminate.
Preferably, the titanate esters are selected from positive isopropyl titanate, positive butyl titanate, butyl titanate mixture, poly- metatitanic acid
Butyl ester, the different monooctyl ester of metatitanic acid four, purity titanium tetraethoxide, four (2-Ethylhexyl Alcohol) titaniums, n-propyl titanate, two oleic acid acyloxy of propyl
(dioctyl phosphoric acid acyloxy) titanate esters, isopropyl three (dioctyl phosphoric acid acyloxy) titanate esters, three oleic acid acyloxy of isopropyl
Titanate esters, isopropyl three (dodecyl benzene sulfonic acid) titanate esters, isopropyl three (dioctylphyrophosphoric acid acyloxy) titanate esters, isopropyl
In (dioctylphyrophosphoric acid acyloxy) the ethylene titanate esters of base three and tetra isopropyl two (dioctyl phosphito acyloxy) titanate esters
It is one or more；
The zirconate is selected from the one or more of zirconium-n-butylate and zirconic acid isobutyl ester kind；
The Aluminate is selected from two (ethyl acetoacetate) aluminic acid diisopropyl esters, aluminic acid isopropyl ester and two (acetylacetone,2,4-pentanediones)
One or more of aluminic acid diisopropyl ester.
Preferably, the solvent is one or more of butyl acetate, propyl acetate, toluene, ethyl acetate and butanone.
The present invention also provides a kind of preparation methods of silicon rubber silane coupling agent described above, comprising the following steps:
Methoxyl group silicone resin, cohesive promoting agent, esters of silicon acis, silane coupling agent, catalysts and solvents are mixed, are obtained silane-modified
Glue silane coupling agent.
Preferably, described be mixed into is stirred, and the mixed temperature is 20~50 DEG C, and the mixed time is 5
~120min.
The present invention provides a kind of silicon rubber silane coupling agents, according to parts by weight include: 5~20 parts of methoxyl group silicone resin；
1~10 part of cohesive promoting agent；1~5 part of esters of silicon acis；1~5 part of silane coupling agent；1~5 part of catalyst；60~90 parts of solvent；The rush
Stick is made by epoxy silane and secondary amine silane reaction；The silane coupling agent is selected from vinyl silane tri-butyl peroxy
And/or double-[γ-(triethoxysilicane) propyl] tetrasulfide.Silicon rubber silane coupling agent provided by the invention can not only improve
Cementability of the single-component silicon rubber in LOW-E glass surface, moreover it is possible to improve two-component silicone rubber in the cementability of LOW-E glass surface.
The experimental results showed that silicon rubber prepared by the present invention either cooperates one-component silicone adhesive to use with silane coupling agent, also
It is that the cohesional failure for cooperating two-component silicone adhesive to use is attained by 85% or even 100%.Therefore, silicon rubber provided by the invention
It can not only make single-component silicon rubber that there is preferably cementability in LOW-E glass surface with silane coupling agent, and two-component can be made
Silicon rubber has preferably cementability in LOW-E glass surface.
Specific embodiment
Below in conjunction with the embodiment of the present invention, technical solution of the present invention is clearly and completely described, it is clear that institute
The embodiment of description is only a part of the embodiment of the present invention, instead of all the embodiments.Based on the embodiments of the present invention,
Every other embodiment obtained by those of ordinary skill in the art without making creative efforts, belongs to this hair
The range of bright protection.
The present invention provides a kind of silicon rubber silane coupling agents, include: according to parts by weight
The cohesive promoting agent is made by epoxy silane and secondary amine silane reaction；
The silane coupling agent is selected from vinyl silane tri-butyl peroxy and/or double-[γ-(triethoxysilicane) propyl]
Tetrasulfide.
Silicon rubber silane coupling agent provided by the invention includes methoxyl group silicone resin.Methoxyl group silicone resin has bi-methoxy,
Membrane structure can be formed with the metal oxide component cross-linking reaction in LOW-E film, improve surface smoothness.The methoxyl group
The parts by weight of silicone resin are 5~20 parts.In certain embodiments of the present invention, the parts by weight of the methoxyl group silicone resin are
7 parts, 15 parts or 18 parts.
In certain embodiments of the present invention, the methoxyl group silicone resin has the structure as shown in formula (I):
In formula (I), R1For hydrogen or methyl；R2For methyl or ethyl；R3For methyl.
In certain embodiments of the present invention, the number-average molecular weight of the methoxyl group silicone resin is 500~5000.Certain
In embodiment, the number-average molecular weight of the methoxyl group silicone resin is 2000,1500,4000 or 3000.
Silicon rubber silane coupling agent provided by the invention further includes cohesive promoting agent.The parts by weight of the cohesive promoting agent are 1~10 part.
In certain embodiments of the present invention, the parts by weight of the cohesive promoting agent are 6 parts, 9 parts or 3 parts.
In certain embodiments of the present invention, the cohesive promoting agent is made by epoxy silane and secondary amine silane reaction.Specifically
, it can be with are as follows: by epoxy silane and secondary amine silane mixture, 30~60min is stirred at 20~60 DEG C, obtains cohesive promoting agent.
In certain embodiments of the present invention, the epoxy silane is selected from γ-glycidyl ether oxygen propyl trimethoxy silicon
Alkane, 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl diethoxy silane, 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl dimethoxysilane,
γ-glycidoxypropyltrietandysilane andysilane, β-(3,4 epoxycyclohexyl)-ethyl triethoxysilane and β-(3,4 rings
One or more of oxygen cyclohexyl)-ethyl trimethoxy silane.
In certain embodiments of the present invention, the secondary amino silanes are selected from N- (normal-butyl)-γ-aminopropyl trimethoxy
Silane, N- cyclohexyl-γ-aminopropyltriethoxy dimethoxysilane, bis- (3- trimethoxy-silylpropyl) amine, double-(γ-
Trimethoxy silicon propyl) in amine, bis- (3- triethoxysilylpropyl) amine and N- phenyl-γ-aminopropyltrimethoxysilane one
Kind is several.
In certain embodiments of the present invention, the mass ratio of the epoxy silane and secondary amine base silane be 23~26:30~
35.In certain embodiments, the mass ratio of the epoxy silane and secondary amine base silane is 23.6:34,26:35,25:35 or 26:
30。
The temperature of the stirring is 20~60 DEG C.In certain embodiments of the present invention, the temperature of the stirring be room temperature,
55 DEG C or 35 DEG C.The time of the stirring is 30~60min.In certain embodiments of the present invention, the time of the stirring is
60min。
Silicon rubber silane coupling agent provided by the invention further includes esters of silicon acis.The parts by weight of the esters of silicon acis are 1~5 part.
In certain embodiments of the present invention, the parts by weight of the esters of silicon acis are 1 part, 3 parts or 4 parts.
In certain embodiments of the present invention, the esters of silicon acis is selected from methyl orthosilicate and/or ethyl orthosilicate.
Silicon rubber silane coupling agent provided by the invention further includes silane coupling agent.The parts by weight of the silane coupling agent are
1~5 part.In certain embodiments of the present invention, the parts by weight of the silane coupling agent are 2 parts, 3 parts or 4 parts.
In the present invention, the silane coupling agent is selected from vinyl silane tri-butyl peroxy and/or double-[γ-(three ethoxies
Base silicon) propyl] tetrasulfide.
Silicon rubber silane coupling agent provided by the invention further includes catalyst.Catalyst in the present invention can accelerate silicon rubber
In the onset time of LOW-E glass surface.The parts by weight of the catalyst are 1~5 part.In certain embodiments of the present invention,
The parts by weight of the catalyst are 1 part, 2 parts, 4 parts or 5 parts.
In certain embodiments of the present invention, the catalyst be selected from one of titanate esters, zirconate and Aluminate or
It is several.
The titanate esters be preferably positive isopropyl titanate, positive butyl titanate, butyl titanate mixture, poly(tributoxy titanium),
The different monooctyl ester of metatitanic acid four, purity titanium tetraethoxide, four (2-Ethylhexyl Alcohol) titaniums, n-propyl titanate, two oleic acid acyloxy (dioctyl of propyl
Phosphoric acid acyloxy) titanate esters, isopropyl three (dioctyl phosphoric acid acyloxy) titanate esters, three oleic acid acyloxy titanate esters of isopropyl,
Isopropyl three (dodecyl benzene sulfonic acid) titanate esters, isopropyl three (dioctylphyrophosphoric acid acyloxy) titanate esters, isopropyl three (two
Octyl pyrophosphoric acid acyloxy) one of ethylene titanate esters and tetra isopropyl two (dioctyl phosphito acyloxy) titanate esters or more
Kind.
The zirconate is preferably the one or more of zirconium-n-butylate and zirconic acid isobutyl ester kind.
The Aluminate is preferably two (ethyl acetoacetate) aluminic acid diisopropyl esters, aluminic acid isopropyl ester and two (levulinics
One or more of ketone) aluminic acid diisopropyl ester.
Silicon rubber silane coupling agent provided by the invention further includes solvent.The parts by weight of the solvent are 60~90 parts.?
In certain embodiments of the present invention, the parts by weight of the solvent are 71 parts, 68 parts, 70 parts, 86 parts or 60 parts.
In certain embodiments of the present invention, the solvent is butyl acetate, propyl acetate, toluene, ethyl acetate and fourth
One or more of ketone.
The present invention also provides a kind of preparation methods of silicon rubber silane coupling agent described above, comprising the following steps:
Methoxyl group silicone resin, cohesive promoting agent, esters of silicon acis, silane coupling agent, catalysts and solvents are mixed, are obtained silane-modified
Glue silane coupling agent.
In certain embodiments of the present invention, described be mixed into is stirred.In certain embodiments of the present invention, described
Mixed temperature is 20~50 DEG C.In certain embodiments, the mixed temperature is room temperature or 50 DEG C.Of the invention certain
In embodiment, the mixed time is 5~120min.In certain embodiments, the mixed time be 60min or
90min。
The present invention has no special limitation to the source of the raw material used above, can be general commercially available.
The present invention provides a kind of silicon rubber silane coupling agents, according to parts by weight include: 5~20 parts of methoxyl group silicone resin；
1~10 part of cohesive promoting agent；1~5 part of esters of silicon acis；1~5 part of silane coupling agent；1~5 part of catalyst；60~90 parts of solvent；The rush
Stick is made by epoxy silane and secondary amine silane reaction；The silane coupling agent is selected from vinyl silane tri-butyl peroxy
And/or double-[γ-(triethoxysilicane) propyl] tetrasulfide.Silicon rubber silane coupling agent provided by the invention can not only improve
Cementability of the single-component silicon rubber in LOW-E glass surface, moreover it is possible to improve two-component silicone rubber in the cementability of LOW-E glass surface.
The experimental results showed that silicon rubber prepared by the present invention either cooperates one-component silicone adhesive to use with silane coupling agent, also
It is that the cohesional failure for cooperating two-component silicone adhesive to use is attained by 85% or even 100%.Therefore, silicon rubber provided by the invention
It can not only make single-component silicon rubber that there is preferably cementability in LOW-E glass surface with silane coupling agent, and two-component can be made
Silicon rubber has preferably cementability in LOW-E glass surface.
In order to further illustrate the present invention, below with reference to embodiment to a kind of silicon rubber silane coupling agent provided by the invention and
Preparation method is described in detail, but they cannot be interpreted as limiting the scope of the present invention.
Raw material used in following embodiment is general commercially available.
Embodiment 1
The preparation of cohesive promoting agent:
By 23.6g γ-glycidyl ether oxygen propyl trimethoxy silicane and 34g bis- (3- trimethoxy-silylpropyls)
Amine mixing, stirring at normal temperature 60min obtain cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For hydrogen；R2For methyl, R3For methyl, molecular weight
It is 2000.
Just by cohesive promoting agent described in methoxyl group silicone resin, 6g described in 15g, 3g methyl orthosilicate, the positive butyl titanate of 1g, 1g zirconic acid
Butyl ester, 3g vinyl silane tri-butyl peroxy and 71g propyl acetate are stirred 60min at normal temperature, obtain silicon rubber use
Silane coupling agent.
Comparative example 1
The preparation of cohesive promoting agent:
By 23.6g γ-glycidyl ether oxygen propyl trimethoxy silicane and 34g bis- (3- trimethoxy-silylpropyls)
Amine mixing, stirring at normal temperature 60min obtain cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For hydrogen；R2For methyl, R3For methyl, molecular weight
It is 2000.
Just by cohesive promoting agent described in methoxyl group silicone resin, 6g described in 15g, 3g methyl orthosilicate, the positive butyl titanate of 1g, 1g zirconic acid
Butyl ester, 3g vinyltrimethoxysilane and 71g propyl acetate are stirred 60min at normal temperature, obtain silicon rubber primary coat
Agent.
Embodiment 2
The preparation of cohesive promoting agent:
By 26g 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl diethoxy silane and bis- (3- triethoxysilylpropyl) amine of 35g
Mixing, in 55 DEG C of stirring 60min, obtains cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For methyl；R2For methyl, R3For methyl, molecule
Amount is 1500.
By cohesive promoting agent described in methoxyl group silicone resin, 9g described in 15g, 1g ethyl orthosilicate, 1g aluminic acid isopropyl ester, 3g isopropyl
Three (dioctylphyrophosphoric acid acyloxy) ethylene titanate esters, 3g vinyl silane tri-butyl peroxy and 68g propyl acetate are in room temperature
Under be stirred 60min, obtain silicon rubber silane coupling agent.
Embodiment 3
The preparation of cohesive promoting agent:
By 26g 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl diethoxy silane and bis- (3- triethoxysilylpropyl) amine of 35g
Mixing, in 55 DEG C of stirring 60min, obtains cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For methyl；R2For ethyl, R3For methyl, molecule
Amount is 4000.
By cohesive promoting agent described in methoxyl group silicone resin, 9g described in 15g, 1g ethyl orthosilicate, 1g aluminic acid isopropyl ester, 3g isopropyl
Three (dioctylphyrophosphoric acid acyloxy) ethylene titanate esters, 4g be bis--[γ-(triethoxysilicane) propyl] tetrasulfide and 70g acetic acid
Propyl ester is stirred 60min at normal temperature, obtains silicon rubber silane coupling agent.
Embodiment 4
The preparation of cohesive promoting agent:
By 25g 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl dimethoxysilane and 35g N- phenyl-γ-aminopropyl front three
Oxysilane mixing, in 35 DEG C of stirring 60min, obtains cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For hydrogen；R2For ethyl, R3For methyl, molecular weight
It is 4000.
By cohesive promoting agent described in methoxyl group silicone resin, 3g described in 7g, 1g ethyl orthosilicate, 0.5g methyl orthosilicate, 0.5g aluminium
Isopropyl propionate, 0.5g zirconic acid isobutyl ester, 2g be bis--and [γ-(triethoxysilicane) propyl] tetrasulfide and 86g ethyl acetate is in room temperature
Under be stirred 90min, obtain silicon rubber silane coupling agent.
Embodiment 5
The preparation of cohesive promoting agent:
By 26g 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl dimethoxysilane and 30g N- cyclohexyl-γ-aminopropyl first
The mixing of base dimethoxysilane, in 55 DEG C of stirring 60min, obtains cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For methyl；R2For methyl, R3For methyl, molecule
Amount is 3000.
Just by cohesive promoting agent described in methoxyl group silicone resin, 9g described in 18g, 2g ethyl orthosilicate, 2g methyl orthosilicate, 2g zirconic acid
Butyl ester, 3g tetra isopropyl two (dioctyl phosphito acyloxy) titanate esters, 2g is bis--and [γ-(triethoxysilicane) propyl] four vulcanize
Object, 2g vinyl silane tri-butyl peroxy, 40g propyl acetate and 20g toluene are stirred 60min at 50 DEG C, obtain silicon
Rubber silane coupling agent.
Comparative example 2
The preparation of cohesive promoting agent:
By 26g 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl diethoxy silane and bis- (3- triethoxysilylpropyl) amine of 35g
Mixing, in 55 DEG C of stirring 60min, obtains cohesive promoting agent.
The preparation of silane coupling agent:
Methoxyl group silicone resin has the structure as shown in formula (I), wherein R1For methyl；R2For methyl, R3For methyl, molecule
Amount is 3000.
By cohesive promoting agent described in methoxyl group silicone resin, 9g described in 15g, 1g ethyl orthosilicate, 4g it is bis--[γ-(triethoxysilicane)
Propyl] tetrasulfide and 70g propyl acetate be stirred 60min at normal temperature, obtain silicon rubber silane coupling agent.
Embodiment 6
The adhesive property for the silicon rubber silane coupling agent that Examples 1 to 5 and comparative example 1~2 obtain is investigated:
After the silicon rubber silane coupling agent is brushed in LOW-E profile face, one-component silicone adhesive, two-component silicone are beaten respectively
Glue.Normal temperature oxidation investigated cementability after 28 days.The results are shown in Table 1.
The adhesive property test result for the silicon rubber silane coupling agent that 1 Examples 1 to 5 of table and comparative example 1~2 obtain
| Single-component silicon rubber | Two-component silicone rubber | |
| Embodiment 1 | 100% cohesional failure | 100% cohesional failure |
| Comparative example 1 | Removing | 20% cohesional failure |
| Embodiment 2 | 90% cohesional failure | 100% cohesional failure |
| Embodiment 3 | 95% cohesional failure | 100% cohesional failure |
| Embodiment 4 | 85% cohesional failure | 100% cohesional failure |
| Embodiment 5 | 100% cohesional failure | 100% cohesional failure |
| Comparative example 2 | 10% cohesional failure | 30% cohesional failure |
As it can be seen from table 1 silicon rubber prepared by the present invention either cooperates one-component silicone adhesive to use with silane coupling agent, also
It is that the cohesional failure for cooperating two-component silicone adhesive to use is attained by 85% or even 100%.Therefore, silicon rubber provided by the invention
It can not only make single-component silicon rubber that there is preferably cementability in LOW-E glass surface with silane coupling agent, and two-component can be made
Silicon rubber has preferably cementability in LOW-E glass surface.
The above description of the embodiment is only used to help understand the method for the present invention and its core ideas.To these embodiments
A variety of modifications will be readily apparent to those skilled in the art, the general principles defined herein can be with
Without departing from the spirit or scope of the present invention, it realizes in other embodiments.Therefore, the present invention will not be limited
In the embodiments shown herein, and it is to fit to widest model consistent with the principles and novel features disclosed in this article
It encloses.
Claims (10)
1. a kind of silicon rubber silane coupling agent, which is characterized in that include: according to parts by weight
The cohesive promoting agent is made by epoxy silane and secondary amine silane reaction；
The silane coupling agent is selected from vinyl silane tri-butyl peroxy and/or double-[γ-(triethoxysilicane) propyl] four sulphur
Compound.
2. silicon rubber silane coupling agent according to claim 1, which is characterized in that the methoxyl group silicone resin has such as formula
(I) structure shown in:
In formula (I), R1For hydrogen or methyl；R2For methyl or ethyl；R3For methyl.
3. silicon rubber silane coupling agent according to claim 1, which is characterized in that the equal molecule of number of the methoxyl group silicone resin
Amount is 500~5000.
4. silicon rubber silane coupling agent according to claim 1, which is characterized in that it is sweet that the epoxy silane is selected from γ-shrink
Oily ether oxygen propyl trimethoxy silicane, 3- (the third oxygen of 2,3- epoxy) hydroxypropyl methyl diethoxy silane, 3- (the third oxygen of 2,3- epoxy)
Hydroxypropyl methyl dimethoxysilane, γ-glycidoxypropyltrietandysilane andysilane, β-(3,4 epoxycyclohexyl)-ethyl three
One or more of Ethoxysilane and β-(3,4 epoxycyclohexyl)-ethyl trimethoxy silane；
The secondary amino silanes are selected from N- (normal-butyl)-γ-aminopropyltrimethoxysilane, N- cyclohexyl-γ-aminopropyltriethoxy
Dimethoxysilane, bis- (3- trimethoxy-silylpropyl) amine, double-(γ-trimethoxy silicon propyl) amine, bis- (tri- second of 3-
Oxygroup silicon propyl) one or more of amine and N- phenyl-γ-aminopropyltrimethoxysilane.
5. silicon rubber silane coupling agent according to claim 1, which is characterized in that the esters of silicon acis is selected from methyl orthosilicate
And/or ethyl orthosilicate.
6. silicon rubber silane coupling agent according to claim 1, which is characterized in that the catalyst is selected from titanate esters, zirconic acid
One or more of ester and Aluminate.
7. silicon rubber silane coupling agent according to claim 6, which is characterized in that the titanate esters are selected from positive metatitanic acid isopropyl
Ester, positive butyl titanate, butyl titanate mixture, poly(tributoxy titanium), the different monooctyl ester of metatitanic acid four, purity titanium tetraethoxide, four (2- ethyl hexyls
Alcohol) titanium, n-propyl titanate, two oleic acid acyloxy of propyl (dioctyl phosphoric acid acyloxy) titanate esters, (the dioctyl phosphorus of isopropyl three
Sour acyloxy) titanate esters, three oleic acid acyloxy titanate esters of isopropyl, isopropyl three (dodecyl benzene sulfonic acid) titanate esters, isopropyl
Base three (dioctylphyrophosphoric acid acyloxy) titanate esters, (dioctylphyrophosphoric acid acyloxy) the ethylene titanate esters of isopropyl three and four isopropyls
One of base two (dioctyl phosphito acyloxy) titanate esters are a variety of；
The zirconate is selected from the one or more of zirconium-n-butylate and zirconic acid isobutyl ester kind；
The Aluminate is selected from two (ethyl acetoacetate) aluminic acid diisopropyl esters, aluminic acid isopropyl ester and two (acetylacetone,2,4-pentanedione) aluminic acids
One or more of diisopropyl ester.
8. silicon rubber silane coupling agent according to claim 1, which is characterized in that the solvent is butyl acetate, acetic acid third
One or more of ester, toluene, ethyl acetate and butanone.
9. the preparation method of silicon rubber silane coupling agent described in claim 1, comprising the following steps:
Methoxyl group silicone resin, cohesive promoting agent, esters of silicon acis, silane coupling agent, catalysts and solvents are mixed, silane-modified glue is obtained and uses
Silane coupling agent.
10. preparation method according to claim 9, which is characterized in that described be mixed into is stirred, the mixed temperature
Degree is 20~50 DEG C, and the mixed time is 5~120min.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910588943.3A CN110256956B (en) | 2019-07-02 | 2019-07-02 | Primer for silicon rubber and preparation method thereof |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201910588943.3A CN110256956B (en) | 2019-07-02 | 2019-07-02 | Primer for silicon rubber and preparation method thereof |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| CN110256956A true CN110256956A (en) | 2019-09-20 |
| CN110256956B CN110256956B (en) | 2021-05-11 |
Family
ID=67923817
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN201910588943.3A Active CN110256956B (en) | 2019-07-02 | 2019-07-02 | Primer for silicon rubber and preparation method thereof |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN110256956B (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111234737A (en) * | 2020-03-11 | 2020-06-05 | 杭州之江新材料有限公司 | Primer, preparation method, bonding method and application |
| CN112625598A (en) * | 2020-12-17 | 2021-04-09 | 成都硅宝科技股份有限公司 | Primer for silicon rubber self-adhesive tape and preparation method thereof |
| CN113717633A (en) * | 2021-05-08 | 2021-11-30 | 杭州师范大学 | Primer for bonding silicon resin thermal protection coating and preparation method and application thereof |
| CN117624604A (en) * | 2024-01-25 | 2024-03-01 | 以诺康医疗科技（苏州）有限公司 | Titanate-silicate oligomer, preparation method thereof, primer containing oligomer and application of primer |
Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4401500A (en) * | 1981-03-27 | 1983-08-30 | Dow Corning Corporation | Primer composition used for adhesion |
| CN101298519A (en) * | 2008-07-01 | 2008-11-05 | 武汉理工大学 | Silastic for joint seal of aqueduct expansion joint and preparation thereof |
| CN102965068A (en) * | 2012-11-28 | 2013-03-13 | 武汉长盈通光电技术有限公司 | Bi-component thermosetting low-viscosity silicon rubber adhesive |
| US20130130022A1 (en) * | 2011-10-14 | 2013-05-23 | Canon Kabushiki Kaisha | Member for electrophotography, process cartridge, and electrophotographic apparatus |
| CN103214946A (en) * | 2013-04-28 | 2013-07-24 | 深圳市新亚新材料有限公司 | Primer coating for single-component room-temperature vulcanized silicone rubber and preparation method thereof |
| CN104497866A (en) * | 2014-12-22 | 2015-04-08 | 广州市白云化工实业有限公司 | Silicone sealant base coat liquid suitable for fiber cement board |
| CN105505084A (en) * | 2014-09-24 | 2016-04-20 | 比亚迪股份有限公司 | Addition-type silicon rubber primer and preparation method thereof |
| CN109321201A (en) * | 2018-09-28 | 2019-02-12 | 深圳市康利邦科技有限公司 | A kind of silicon rubber silane coupling agent and preparation method thereof |
| CN109468116A (en) * | 2018-10-22 | 2019-03-15 | 杭州之江新材料有限公司 | A kind of dealcoholized type bi-component Silica hydrogel and preparation method thereof |
| CN109852332A (en) * | 2018-12-05 | 2019-06-07 | 湖北航天化学技术研究所 | A kind of surface treating agent and its preparation method and application |
-
2019
- 2019-07-02 CN CN201910588943.3A patent/CN110256956B/en active Active
Patent Citations (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4401500A (en) * | 1981-03-27 | 1983-08-30 | Dow Corning Corporation | Primer composition used for adhesion |
| CN101298519A (en) * | 2008-07-01 | 2008-11-05 | 武汉理工大学 | Silastic for joint seal of aqueduct expansion joint and preparation thereof |
| US20130130022A1 (en) * | 2011-10-14 | 2013-05-23 | Canon Kabushiki Kaisha | Member for electrophotography, process cartridge, and electrophotographic apparatus |
| CN102965068A (en) * | 2012-11-28 | 2013-03-13 | 武汉长盈通光电技术有限公司 | Bi-component thermosetting low-viscosity silicon rubber adhesive |
| CN103214946A (en) * | 2013-04-28 | 2013-07-24 | 深圳市新亚新材料有限公司 | Primer coating for single-component room-temperature vulcanized silicone rubber and preparation method thereof |
| CN105505084A (en) * | 2014-09-24 | 2016-04-20 | 比亚迪股份有限公司 | Addition-type silicon rubber primer and preparation method thereof |
| CN104497866A (en) * | 2014-12-22 | 2015-04-08 | 广州市白云化工实业有限公司 | Silicone sealant base coat liquid suitable for fiber cement board |
| CN109321201A (en) * | 2018-09-28 | 2019-02-12 | 深圳市康利邦科技有限公司 | A kind of silicon rubber silane coupling agent and preparation method thereof |
| CN109468116A (en) * | 2018-10-22 | 2019-03-15 | 杭州之江新材料有限公司 | A kind of dealcoholized type bi-component Silica hydrogel and preparation method thereof |
| CN109852332A (en) * | 2018-12-05 | 2019-06-07 | 湖北航天化学技术研究所 | A kind of surface treating agent and its preparation method and application |
Non-Patent Citations (5)
| Title |
|---|
| AYANO SHINOHARA 等: "Effects of three silane primers and five adhesive agents on the bond strength of composite material for a computer-aided design and manufacturing system", 《JOURNAL OF APPLIED ORAL SCIENCE》 * |
| SUNG-SEEN CHOI等: "Influence of TESPT Content on Crosslink Types and Rheological Behaviors of Natural Rubber Compounds Reinforced with Silica", 《JOURNAL OF APPLIED POLYMER SCIENCE》 * |
| 李云龙等: "聚氨酯风挡胶底涂技术进展", 《粘结》 * |
| 董运生等: "用于聚对苯二甲酸乙二醇酯（PET）薄膜与加成型有机硅粘接的底涂剂制备与表征", 《当代化工》 * |
| 黄海龙等: "硅橡胶界面粘接增强技术概述", 《化学工程师》 * |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN111234737A (en) * | 2020-03-11 | 2020-06-05 | 杭州之江新材料有限公司 | Primer, preparation method, bonding method and application |
| CN112625598A (en) * | 2020-12-17 | 2021-04-09 | 成都硅宝科技股份有限公司 | Primer for silicon rubber self-adhesive tape and preparation method thereof |
| CN113717633A (en) * | 2021-05-08 | 2021-11-30 | 杭州师范大学 | Primer for bonding silicon resin thermal protection coating and preparation method and application thereof |
| CN117624604A (en) * | 2024-01-25 | 2024-03-01 | 以诺康医疗科技（苏州）有限公司 | Titanate-silicate oligomer, preparation method thereof, primer containing oligomer and application of primer |
| CN117624604B (en) * | 2024-01-25 | 2024-04-16 | 以诺康医疗科技（苏州）有限公司 | Titanate-silicate oligomer, preparation method thereof, primer containing oligomer and application of primer |
Also Published As
| Publication number | Publication date |
|---|---|
| CN110256956B (en) | 2021-05-11 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| CN110256956A (en) | A kind of silicon rubber silane coupling agent and preparation method thereof | |
| CN109796871B (en) | Flexible ceramic coating and preparation method thereof | |
| CN103820072B (en) | Double-component silicone structural sealant for heat mirror hollow glass and preparation method thereof | |
| CN109280533B (en) | Single-component dealcoholized transparent silicone sealant and preparation method and application thereof | |
| CN101298550B (en) | Nanometer mildewproof sealing neutral silicone resin | |
| CN105176211A (en) | Organic-inorganic composite thermal insulation paint and preparation method thereof | |
| CN110183878A (en) | A kind of ceramic coating and preparation method thereof with environmental protection self-cleaning antibacterial damage resistant effect | |
| CN103555198B (en) | The preparation method of modified organic silicone resin coating liquid and the method with its manufacture packaging glass of solar cell | |
| CN110157329A (en) | A kind of nano-composite coating material | |
| CN107083185A (en) | A kind of aluminum alloy doors and windows heat-insulated protective coating and preparation method thereof | |
| CN109135650B (en) | Single-component silane modified polyether sealant and preparation method thereof | |
| CN113337245A (en) | Dealcoholized photovoltaic module sealant and preparation method thereof | |
| CN109161311A (en) | High adhesion force Heat Resistant Powder Coatings polyester resin and preparation method thereof | |
| CN113897171B (en) | Preparation method of high-displacement dealcoholized flame-retardant fireproof sealant | |
| JP4484602B2 (en) | How to renovate building exterior | |
| CN109897182A (en) | A kind of aqueous macromolecular amount silane coupling agent and preparation method thereof | |
| KR101800969B1 (en) | Aqueous Paint Composition | |
| CN109370425A (en) | A kind of wear-resistant coating liquid and preparation method thereof for polycarbonate lens | |
| CN110256930B (en) | High-performance organic silicon coating | |
| CN112480860A (en) | Single-component silicone sealant with excellent yellowing resistance and weather resistance and preparation method thereof | |
| CN112266678A (en) | Waterproof coating for external wall and preparation method thereof | |
| CN110804360A (en) | APAO modified silicone-acrylic emulsion anti-sagging coating | |
| CN108218243A (en) | A kind of nanometer thermal insulation coating applied on hollow glass | |
| CN110194933A (en) | A kind of silane-modified glue silane coupling agent and preparation method thereof | |
| CN114369408A (en) | Coating, color film and photovoltaic module |
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 | ||
| GR01 | Patent grant |