CN106753060B - A kind of Heat vulcanization adhesive of silane coupling agent base - Google Patents
A kind of Heat vulcanization adhesive of silane coupling agent base Download PDFInfo
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- CN106753060B CN106753060B CN201610998020.1A CN201610998020A CN106753060B CN 106753060 B CN106753060 B CN 106753060B CN 201610998020 A CN201610998020 A CN 201610998020A CN 106753060 B CN106753060 B CN 106753060B
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- coupling agent
- silane coupling
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- adhesive
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- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/541—Silicon-containing compounds containing oxygen
- C08K5/5425—Silicon-containing compounds containing oxygen containing at least one C=C bond
-
- 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
- C08K5/00—Use of organic ingredients
- C08K5/54—Silicon-containing compounds
- C08K5/548—Silicon-containing compounds containing sulfur
-
- 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
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
A kind of Heat vulcanization adhesive of novel silane coupler base, its composition include a：A kind of general formula is Resin R1SiR3Olefin-containing functional group modified silane coupler；b：A kind of general formula is R2SiR3The silane coupling agent containing sulfydryl；c：A kind of general formula is R3Si‑(OOR4)3The silane coupling agent containing peroxy；d：Alcohols solvent；In above-mentioned each general formula, R selected from halogen, acetoxyl group, 15 carbon atoms alkoxy in one kind；R1For alkylene；R2For the sulfydryl of big molecular modification；R3For alkylene；R4For tertiary butyl or the tert-butyl group；Resin is halogenated polyolefin.The adhesive can be to producing excellent binding ability between the various rubber of Elastomers with Different Curing Systems, different rigid substrates, adhesive strength is high.
Description
Technical field
The present invention relates to Heat vulcanization adhesive field, and in particular to a kind of rubber based on modified silane coupler and
Rigid substrate bonding Heat vulcanization adhesive.
Background technology
In rubber industry, need with materials such as metal, ceramics to have been combined rubber by bonding effect in many cases
Come, adhesive technology is widely used in the industries such as tire, adhesive tape, damping, sealing.At present commercially using very extensive
Rubber and metal adhesive technology be from the 1950s, by LORD companies US 2900292, take the lead in the Chemlok released
220 and Chemlok 205.Its main component is polymer, vulcanizing agent, color stuffing organic solvent dispersion.It is this heterogeneous
Precipitation and lamination occurs in system in placement process.Need to be stirred adhesive before construction, in addition this
The adhesive of type needs have more fine control to the thickness of coating in the construction process；Hereafter LORD is proposed water again
Based adhesive, aqua type Heat vulcanization adhesive are to be dispersed in water polymer micelle, its storage stability is there are it intrinsic
Defect, its pretreatment of base material to coating requires very high in addition, and needs to be equipped with dedicated drying line and matched somebody with somebody with paint line
Set, so as to considerably increase the difficulty of construction.
Silanes adhesive has certain application in bonding hot vulcanization.It is concentrated mainly on fluorine in bonding hot vulcanization at present
In the bonding of rubber and metal.Hydrogen atom is very high and fluorine atom of relatively large radius substitutes, its conformation by electronegativity in fluorubber
State is unfolded from chain segmentation and is changed into spiral winding state, therefore the increase of its surface inertness, reactivity declines, the tack of fluorubber and
Mutual viscosity is all poor.
The special-purpose adhesive of current existing fluorubber and metal adhesive has Kai Muluoke607、AP-133、5150、512 and western nation of BritainIts is current
The scope of application of this adhesive classes is very narrow, can only produce bonding effect to the rubber of specific vulcanizing system；CH5150、
The fluororubber binding that CH607 vulcanizes amine is preferable, but poor to the fluororubber binding applicability of peroxide vulcanizing system,
In addition its adhesive property to metal base is also poor；Adhesive and some amines (N, N '-bis- Chinese cassia trees
Fork base -1,6- hexamethylene diamines) fluorubber of vulcanizing system vulcanization cannot effectively be bonded；With gluing for peroxide (DCP) vulcanized rubber
It is also slightly worse to connect performance；Silane addition coupling agent is bonding with silicon rubber as fluororubber with surface wettability and caking property
In also have certain application, but if desired ensure preferable adhesive effect, it is necessary to silastic surface carry out it is complex before
Processing, while need have very high requirement to ambient humidity etc..
The patents such as US 5907015, US 5532314 describe aqua type silane crosslinker be used for rubber and metal/ceramic/
The adhesive of glass bonding, its adhesive rubber species is more, but all there are larger for its storage stability and technique applicability etc.
The defects of；US 2003004295 describes a kind of silane coupling agent containing amino and the institute of the silane copolymer containing vinyl
The adhesive obtained, its fluororubber binding to polyol and peroxide cure has preferable effect, but it is
Water-based adhesive, itself storage stability and construction etc. there is it is larger the defects of；JP2004168884 is then by ring
Oxygen tree fat, two kinds of silane coupling agents, titanate esters, isocyanuric acid ester mixing, then use it for the bonding of low temperature resistant fluorubber,
Rubber coating rate can reach 100%.US 6409874 then describes the silane type adhesive of ethanol/water mixed solvent type, its is main
Component is a kind of silane coupling agent of organo-functional group and the silane compound without organo-functional group, it is primarily adapted for use in fluorine silicon
Rubber is bonding with metal, its adhesive strength is higher, and bonding interface medium-resistance is preferable.
The content of the invention
The object of the present invention is to provide the silane coupled formulation heat cure of a kind of general purpose rubber and different rigidity substrate bonding
Adhesive.It can be used for the rubber of the Elastomers with Different Curing Systems such as nitrile rubber, neoprene, natural rubber, ethylene propylene diene rubber with
The bonding of a variety of rigid substrates such as steel, aluminium, iron, ceramics, fiber.In the case where ensureing that adhesive strength is identical, it is to thickness
It is required that it is much smaller than traditional solvent-based adhesive.
It is a further object of the present invention to provide a kind of coupling agent used of the Heat vulcanization adhesive of above-mentioned silane coupling agent base
Method of modifying, to silane coupler modified, so as to increase its scope of application to different rubber.By chloridized polyolefin to silicon
Alkane coupling agent is modified, and the stronger chloridized polyolefin of polarity can be obviously improved attachment and the bonding of adhesive and metal base.
It is a further object of the present invention to provide the preparation method of the Heat vulcanization adhesive of this silane coupling agent base.This
Heat vulcanization adhesive due to being not directed to the scattered etc. of color stuffing, stablize by its simple production process, quality control.
The first aspect of the present invention provides a kind of Heat vulcanization adhesive of silane coupling agent base, and composition includes：
Component a：A kind of general formula is Resin-g-R1SiR3Olefin-containing functional group modified silane coupler；
Component b：A kind of general formula is R2SiR3The modified silane coupler containing sulfydryl；
Component c：A kind of general formula is R3Si-(OOR4)3The modified silane coupler containing peroxy；
Component d：Alcohols solvent；
In above-mentioned each general formula, R selected from halogen, acetoxyl group, 1-5 carbon atom alkoxy in one kind；R1For alkene
Base；R2For the sulfydryl of big molecular modification；R3For alkylene；R4For tertiary butyl or the tert-butyl group；Resin is halogenated polyolefin.
In some embodiments, the R is the alkoxy of 1-5 carbon atom.
In some embodiments, the R1For the double bond containing alkylene of 2-8 carbon atom, the R2For 3-5
The sulfydryl of carbon atom, the R3For the double bond containing alkylene of 2-8 carbon atom.
In some embodiments, the component a is by including containing R1The raw material of unmodified silane coupling agent be prepared,
It is described to contain R1Unmodified silane coupling agent be selected from allyltrimethoxysilanis, allyltriethoxysilane, vinyl three
One kind in methoxy silane, vinyltriethoxysilane.
In some embodiments, the component b is by including containing R2The raw material of unmodified silane coupling agent be prepared,
It is described to contain R2Unmodified silane coupling agent be selected from γ-mercaptopropyl trimethoxysilane, γ-thiocyanogen propyl-triethoxysilicane
One kind in alkane, double (triethoxy silicon substrate propyl group) tetrasulfides, double (triethoxy silicon substrate propyl group) disulphide.
In some embodiments, the component c is by including containing R3The raw material of unmodified silane coupling agent be prepared,
It is described to contain R3Unmodified silane coupling agent be selected from vinyl silane tri-butyl peroxy, three tert-butylperoxy base silane of methyl,
One kind in vinyl methyl ethyl tert-butylperoxy base silane, three tert-butylperoxy silane of vinyl.
In some embodiments, the halogenated polyolefin gathers selected from chlorinated natural rubber, chlorosulfonated polyethylene, chlorination
Ethene, chlorinated polypropylene, modified chlorinated polypropylene, chlorinated ethylene propylene copolymer, ethylene chloride-ethylene acetate copolymer, chlorine
Change the one or more in propylene -2- butylene copolymers.
In some embodiments, the Heat vulcanization adhesive of the silane coupling agent base, by weight, each group
Distribution ratio is as follows：
In some embodiments, the component a is selected from halogenated polyolefin grafting allyltrimethoxysilanis, halogenation
Polyolefin graft allyltriethoxysilane, halogenated polyolefin grafting vinyl trimethoxy silane, halogenated polyolefin grafting
One kind in vinyltriethoxysilane；The component b is selected from γ-mercaptopropyl trimethoxysilane, γ-thiocyanogen propyl group
One in triethoxysilane, double (triethoxy silicon substrate propyl group) tetrasulfides, double (triethoxy silicon substrate propyl group) disulphide
Kind；The component c is selected from vinyl silane tri-butyl peroxy, three tert-butylperoxy base silane of methyl, vinyl methyl second
One kind in base tert-butylperoxy base silane, three tert-butylperoxy silane of vinyl.
The second aspect of the present invention provides a kind of preparation side of the Heat vulcanization adhesive of silane coupling agent base as described above
Method, includes the following steps：Component a is synthesized, component a and constituent part d is mixed, is finally mixed into component b, component c, then mix
Enter remaining ingredient d, 50 degrees Celsius of sealings are placed 10 days, sealed again after deflation, to obtain the final product.
It is adapted to the present invention's to contain R1Unmodified silane coupling agent instantiation, include but not limited to：Pi-allyl front three
Oxysilane, allyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, γ-pi-allyl three
Methoxy silane, γ-allyltriethoxysilane, γ-acrylic tripropoxy silane, three butoxy silane of γ-acrylic,
It is preferred that γ-allyltrimethoxysilanis, γ-allyltriethoxysilane.
It is adapted to the present invention's to contain R2Unmodified silane coupling agent instantiation, include but not limited to：γ-mercapto propyl group three
Methoxy silane, γ-thiocyanatopropyltriethoxysilane, double (triethoxy silicon substrate propyl group) tetrasulfides, double (triethoxies
Silicon substrate propyl group) disulphide, preferably double (triethoxy silicon substrate propyl group) tetrasulfides, double (triethoxy silicon substrate propyl group) curing
Thing.
It is adapted to the present invention's to contain R3Unmodified silane coupling agent instantiation, include but not limited to：Three uncle of vinyl
Butyl peroxy silane, three tert-butylperoxy base silane of methyl, vinyl methyl ethyl tert-butylperoxy base silane, vinyl three are special
Butyl peroxy silane, preferred vinyl tri-tert peroxy-silane, vinyl methyl ethyl tert-butylperoxy base silane.
Method of modifying in the present invention is as follows：
Chlorinated polyolefin resin, peroxide initiator, the function monomer with blocked isocyanate functional group are carried out
Physical mixed, then makes vistanex that graft reaction occur in molten state and function monomer with extruding graft method, obtains band envelope
The functional polyolefin of closed form isocyanate functional group, afterwards again and the silane coupling agent containing unsaturated double-bond be grafted it is anti-
Should；Or chloridized polyolefin, vinyl monomer and silane coupling agent containing unsaturated double-bond are connect according to a certain percentage
Branch reacts, and the tertiary carbon and secondary carbon position on the modified chlorinated polyolefin long-chain of gained are grafted with blocked isocyanate, vinyl list
Body and silane coupling agent.Active group wherein on blocked isocyanate, vinyl monomer and silane coupling agent is in heat cure
During with rubber crosslink sulfurization, modified chlorinated polyolefin-NCO group and silane coupling agent alkoxy and gold
Belong to or the hydroxyl of ceramic substrate surface is had an effect, so that rubber and base material produce preferable adhesive effect.
It is adapted to the instantiation of the halogenated polyolefin of the present invention, includes but not limited to：The poly- second of chlorinated natural rubber, chlorosulfonation
Alkene, haloflex, chlorinated polypropylene, modified chlorinated polypropylene, chlorinated ethylene propylene copolymer, ethylene chloride-ethylene acetate
Copolymer, preferably propylene dichloride -2- butylene copolymers, chlorinated natural rubber, chlorosulfonated polyethylene.
The instantiation of alcohols solvent includes but not limited to：Methanol, ethanol, propyl alcohol, butanol.Preferred alcohol.
When preparing Heat vulcanization adhesive of the present invention, it is necessary to pay attention to charging sequence and dosage, it is characterised in that each
The modification of component and blend step are as follows：It is the synthesis of a components first, by chloridized polyolefin, vinyl monomer and contains insatiable hunger
Mixed according to a certain percentage with the silane coupling agent of double bond, by azo or peroxide initiation reaction, generate olefin-containing official
The chloridized polyolefin modified silane coupler that can be rolled into a ball；A components are dispersed in enough alcohols solvents afterwards, stirring ensures scattered
Uniformly, other two kinds of silane coupling agents are separately added into afterwards, add remaining alcohols solvent, sealing placement 10 after stirring evenly
Remove sealing after it to discharge the gas for reacting generation.
Heat vulcanization adhesive adhesive rubber species is extensive corresponding to the present invention, from nitrile rubber, neoprene, butylbenzene rubber
Glue, natural rubber, butadiene rubber, butyl rubber and ethylene propylene diene rubber；The species of bonding base material has iron, steel, aluminium, magnesium, pottery
Porcelain, fiber etc..
Specific embodiment
The present invention is further illustrated with case study on implementation, but the present invention is not limited to these cases below.
In each embodiment, the dosage of each component refers both to " parts by weight ", and the bonding strength (MPa) is by GB/T 7760-
2003 measure；
In order to make sample, with tetrachloro-ethylene steam by the steel disc degreasing Jing Guo blasting treatment, and dry.Steel disc according to
It is prepared by the requirement of GB/T7760-2003, thickness is 1.5mm ± 0.1mm, such as using plastic plate or other plates when suitably thicken,
The width of steel disc is that 25mm ± 0.5mm length is 60mm ± 1mm.Before adhesive is applied, steel disc test specimen two ends are covered
17.5mm and 17.5mm, to prevent the region to can be used for being bonded on rubber, leaves the center of 25mm long and 25mm ± 0.5mm wide
Region is to provide on rubber.Then by the adhesive of the example 1-9 of steel disc coating about 1um thickness.
The natural rubber rubber compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.Heat cure vulcanizes the measure of rubber or thermoplastic elastomer and hard plate material bonding strength according to GB/T776-2003 after bonding
It is detected, the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
The DCP ethylene propylene diene rubber rubber compounds vulcanized are placed on each test specimen, and the sulphur under 180 DEG C, the pressure of 10MPa
Change 10 minutes.Vulcanize rubber or thermoplastic elastomer and hard plate material bonding strength according to GB/T776-2003 after heat cure bonding
Measure is detected, and the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
In order to make sample, with tetrachloro-ethylene steam by galvanized sheet degreasing, and dry.Galvanized sheet is according to GB/T7760-
It is prepared by 2003 requirement, thickness is 1.5mm ± 0.1mm, such as using plastic plate or other plates when suitably thicken, the width of galvanized sheet
It is 60mm ± 1mm to spend for 25mm ± 0.5mm length.Before adhesive is applied, cover galvanized sheet test specimen two ends 17.5mm and
17.5mm, to prevent the region to can be used for being bonded on rubber, leaves the central area of 25mm long and 25mm ± 0.5mm wide to carry
It is supplied on rubber.Then by the adhesive of the example 1-9 of galvanized sheet coating about 1um thickness.
The natural rubber rubber compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.Heat cure vulcanizes the measure of rubber or thermoplastic elastomer and hard plate material bonding strength according to GB/T776-2003 after bonding
It is detected, the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
In order to make sample, with tetrachloro-ethylene steam by alumina ceramic plate degreasing, and dry.Alumina ceramic plate according to
Prepared by the requirement of GB/T7760-2003, thickness is 3.0mm ± 0.1mm, and the width of alumina ceramic plate is 25mm ± 0.5mm long
Spend for 60mm ± 1mm.Before adhesive is applied, the 17.5mm and 17.5mm of alumina ceramic plate test specimen two ends are covered, to prevent
Only the region can be used for being bonded on rubber, leave the central area of 25mm long and 25mm ± 0.5mm wide to provide on rubber.
Then by the adhesive of the example 1-9 of galvanized sheet coating about 1um thickness.
The natural rubber rubber compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.Heat cure vulcanizes the measure of rubber or thermoplastic elastomer and hard plate material bonding strength according to GB/T776-2003 after bonding
It is detected, the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
Claims (7)
1. a kind of Heat vulcanization adhesive of silane coupling agent base, it is characterised in that composition includes：
Component a：A kind of general formula is Resin-g-R1SiR3Olefin-containing functional group modified silane coupler；
Component b：Double (triethoxy silicon substrate propyl group) tetrasulfides；
Component c：Vinyl methyl ethyl tert-butylperoxy base silane；
Component d：Alcohols solvent；
In above-mentioned each general formula, R selected from halogen, acetoxyl group, 1-5 carbon atom alkoxy in one kind；R1For alkylene；
Resin is halogenated polyolefin.
2. the Heat vulcanization adhesive of silane coupling agent base as claimed in claim 1, it is characterised in that the R is 1-5 carbon
The alkoxy of atom.
3. the Heat vulcanization adhesive of silane coupling agent base as claimed in claim 1, it is characterised in that the R1For 2-8 carbon
The double bond containing alkylene of atom.
4. the Heat vulcanization adhesive of silane coupling agent base as claimed in claim 1, it is characterised in that the component a by including
Containing R1The raw material of unmodified silane coupling agent be prepared, it is described to contain R1Unmodified silane coupling agent be selected from pi-allyl front three
One kind in oxysilane, allyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane.
5. the Heat vulcanization adhesive of silane coupling agent base as claimed in claim 1, it is characterised in that the halogenated polyolefin
Selected from chlorinated natural rubber, chlorosulfonated polyethylene, haloflex, chlorinated polypropylene, modified chlorinated polypropylene, ethlyene dichloride-
One or more in propylene copolymer, ethylene chloride-ethylene acetate copolymer, propylene dichloride -2- butylene copolymers.
6. the Heat vulcanization adhesive of silane coupling agent base as claimed in claim 1, it is characterised in that by weight, described
Each group distribution ratio is as follows：
A kind of 7. preparation of the Heat vulcanization adhesive of silane coupling agent base as described in any one of claim 1-6 claim
Method, it is characterised in that include the following steps：Component a is synthesized, component a and constituent part d is mixed, is finally mixed into group
Divide b, component c, be blended into remaining ingredient d, 50 degrees Celsius of sealings are placed 10 days, sealed again after deflation, to obtain the final product.
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| CN111100335B (en) * | 2018-10-29 | 2022-03-22 | 北京彤程创展科技有限公司 | Organosilane coated steel wire compound for rubber, preparation method and coating method |
| CN112250919A (en) * | 2020-10-09 | 2021-01-22 | 东莞铧冠橡塑制品有限公司 | Yellowing-resistant rubber for soles and preparation method thereof |
| CN112341956A (en) * | 2020-11-11 | 2021-02-09 | 青岛海力威新材料科技股份有限公司 | Heat vulcanization adhesive for fluororubber oil seal and preparation method |
| CN112680179B (en) * | 2020-12-25 | 2022-10-28 | 苏州禾川化学技术服务有限公司 | Nano interface treating agent for silicon sulfide rubber and preparation method thereof |
| CN112898105A (en) * | 2021-02-09 | 2021-06-04 | 北京理工大学 | Sulfur-free nitrogen-free high-temperature-resistant environment-friendly firework propellant and preparation method thereof |
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| JP5889088B2 (en) * | 2012-03-30 | 2016-03-22 | リンテック株式会社 | Adhesive composition and adhesive sheet |
| CN103059785B (en) * | 2012-12-25 | 2015-06-24 | 江苏鹿山光伏科技有限公司 | Heat resistant type transparent polyolefin hot melt adhesive and preparing method thereof |
| CN103074009B (en) * | 2013-01-24 | 2015-01-07 | 上海普力通新材料科技有限公司 | Adhesion promoter for bonding elastomers and metals and adhesive composition |
| CN103627345A (en) * | 2013-11-07 | 2014-03-12 | 贾梦虹 | Silane coupling agent and preparation method thereof as well as metal adhesive containing silane coupling agent |
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