CN106753060A - A kind of Heat vulcanization adhesive of novel silane coupler base - Google Patents
A kind of Heat vulcanization adhesive of novel silane coupler base Download PDFInfo
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- CN106753060A CN106753060A CN201610998020.1A CN201610998020A CN106753060A CN 106753060 A CN106753060 A CN 106753060A CN 201610998020 A CN201610998020 A CN 201610998020A CN 106753060 A CN106753060 A CN 106753060A
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- Prior art keywords
- silane coupler
- silane
- component
- base
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Classifications
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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
Abstract
A kind of Heat vulcanization adhesive of novel silane coupler base, its composition includes a：A kind of formula is Resin R1SiR3Olefin-containing functional group modified silane coupler；b：A kind of formula is R2SiR3The silane coupler containing sulfydryl；c：A kind of formula is R3Si‑(OOR4)3The silane coupler containing peroxy；d：Alcohols solvent；In above-mentioned each formula, R is selected from the one kind in the alkoxy of halogen, acetoxyl group, 15 carbon atoms；R1It is alkylene；R2It is the sulfydryl of big molecular modification；R3It is alkylene；R4It is 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, and 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 to have been combined the materials such as rubber and metal, ceramics 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 that from the 1950's, by LORD companies US 2900292, take the lead in the Chemlok for releasing
220 and Chemlok 205.Its main component is polymer, vulcanizing agent, color stuffing organic solvent dispersion.It is this heterogeneous
System occurs precipitation and lamination in placement process.Needed to be stirred adhesive before construction, in addition this
The adhesive of type needs have more fine control to the thickness for coating in work progress；Hereafter LORD is proposed water again
Based adhesive, aqua type Heat vulcanization adhesive is to be dispersed in water polymer micelle, and it is intrinsic that its storage stability has its
Defect, its pretreatment of base material requirement to coating is very high in addition, and the drying line for needing outfit special is 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 by electronegativity is very high and the substitution of fluorine atom of relatively large radius, its conformation in fluorubber
State is unfolded from chain segmentation and is changed into spiral winding state, therefore the increase of its surface inertness, reactivity decline, 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 Britain33AB.Its 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 to amine is preferable but poor to the fluororubber binding applicability of peroxide vulcanizing system, this
Outer its adhesive property to metal base is also poor；33AB adhesive and some amine (N, N '-bis- Chinese cassia tree forks
Base -1,6- hexamethylene diamines) vulcanizing system vulcanization fluorubber can not effectively be bonded；It is bonding with peroxide (DCP) vulcanized rubber
Performance is also slightly worse；Silane addition coupling agent with surface wettability and caking property it is bonding with silicon rubber as fluororubber in
Also there is certain application, but if desired ensure preferable adhesive effect, it is necessary to carry out complex preceding place to silastic surface
Reason, while needing have requirement very high to ambient humidity etc..
The patents such as US 5907015, US 5532314 describe aqua type silane crosslinker for rubber and metal/ceramic/
The adhesive of glass bonding, its adhesive rubber species is more, but its storage stability and technique applicability etc. all exist it is larger
Defect；US 2003004295 describes a kind of silane coupler containing amino and the institute of the silane copolymer containing vinyl
The adhesive for obtaining, its fluororubber binding to polyol and peroxide cure has preferable effect, but it is
Water-based adhesive, itself storage stability and construction etc. have larger defect；JP2004168884 is then by ring
Oxygen tree fat, two kinds of silane couplers, 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, and its is main
Composition is a kind of silane coupler of organo-functional group and the silane compound without organo-functional group, and it is primarily adapted for use in fluorine silicon
Rubber is bonding with metal, and its adhesive strength is higher, and bonding interface medium-resistance is preferable.
The content of the invention
It is an object of the invention 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 various rigid substrates such as steel, aluminium, iron, ceramics, fiber.In the case of adhesive strength identical is ensured, it is to thickness
It is required that being 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 coupler 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 novel silane coupler base.This
Plant new Heat vulcanization adhesive steady due to being not directed to dispersion of color stuffing etc., therefore its simple production process, quality control
It is fixed.
The first aspect of the present invention provides a kind of Heat vulcanization adhesive of novel silane coupler base, and composition includes：
Component a：A kind of formula is Resin-g-R1SiR3Olefin-containing functional group modified silane coupler；
Component b：A kind of formula is R2SiR3The modified silane coupler containing sulfydryl；
Component c：A kind of formula is R3Si-(OOR4)3The modified silane coupler containing peroxy；
Component d：Alcohols solvent；
In above-mentioned each formula, R is selected from the one kind in the alkoxy of halogen, acetoxyl group, 1-5 carbon atom；R1It is alkene
Base；R2It is the sulfydryl of big molecular modification；R3It is alkylene；R4It is tertiary butyl or the tert-butyl group；Resin is halogenated polyolefin.
In some embodiments, described R is the 1-5 alkoxy of carbon atom.
In some embodiments, described R1It is the 2-8 double bond containing alkylene of carbon atom, described R2It is 3-5
The sulfydryl of carbon atom, described R3It is the 2-8 double bond containing alkylene of carbon atom.
In some embodiments, the component a is by including containing R1The raw material of unmodified silane coupler prepare,
It is described containing R1Unmodified silane coupler be selected from allyltrimethoxysilanis, allyltriethoxysilane, vinyl three
One kind in methoxy silane, VTES.
In some embodiments, the component b is by including containing R2The raw material of unmodified silane coupler prepare,
It is described containing R2Unmodified silane coupler 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 coupler prepare,
It is described containing R3Unmodified silane coupler be selected from vinyl silane tri-butyl peroxy, the tert-butylperoxy base silane of methyl three,
One kind in vinyl methyl ethyl tert-butylperoxy base silane, the tert-butylperoxy silane of vinyl three.
In some embodiments, described 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 propylene -2- butylene copolymers in one or more.
In some embodiments, the Heat vulcanization adhesive of described novel silane coupler base, it is by weight, described
Each group distribution ratio is as follows：
In some embodiments, described 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 VTES；Described component b is selected from γ-mercaptopropyl trimethoxysilane, γ-thiocyanogen propyl group
In triethoxysilane, double (triethoxy silicon substrate propyl group) tetrasulfides, double (triethoxy silicon substrate propyl group) disulphide one
Kind；Described component c is selected from vinyl silane tri-butyl peroxy, the tert-butylperoxy base silane of methyl three, vinyl methyl second
One kind in base tert-butylperoxy base silane, the tert-butylperoxy silane of vinyl three.
The second aspect of the present invention provides a kind of system of the Heat vulcanization adhesive of novel silane coupler base as described above
Preparation Method, comprises the following steps：Synthesis component a, component a and constituent part d is mixed, and is finally mixed into component b, component c,
Remaining ingredient d is blended into, 50 degrees Celsius of sealings are placed 10 days, sealed again after deflation, obtain final product.
It is adapted to of the invention containing R1Unmodified silane coupler instantiation, including but not limited to：Pi-allyl front three
TMOS, allyltriethoxysilane, vinyltrimethoxy silane, VTES, γ-pi-allyl three
Methoxy silane, γ-allyltriethoxysilane, γ-acrylic tripropoxy silane, the butoxy silane of γ-acrylic three,
It is preferred that γ-allyltrimethoxysilanis, γ-allyltriethoxysilane.
It is adapted to of the invention containing R2Unmodified silane coupler instantiation, including 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 of the invention containing R3Unmodified silane coupler instantiation, including but not limited to：The uncle of vinyl three
Butyl peroxy silane, the tert-butylperoxy base silane of methyl three, 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 coupler containing unsaturated double-bond be grafted it is anti-
Should；Or connect chloridized polyolefin, vinyl monomer and silane coupler containing unsaturated double-bond according to a certain percentage
Branch reaction, 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 coupler.Active group wherein on blocked isocyanate, vinyl monomer and silane coupler is in heat cure
During crosslink sulfurization with rubber, modified chlorinated polyolefin-NCO group and silane coupler alkoxy and gold
The hydroxyl of category or ceramic substrate surface is had an effect, so that rubber and base material produce preferable adhesive effect.
It is adapted to the instantiation of halogenated polyolefin of the invention, including 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 is included but is not limited to：Methyl alcohol, ethanol, propyl alcohol, butanol.Preferred alcohol.
When Heat vulcanization adhesive of the present invention is prepared, it is necessary to note charging sequence and consumption, it is characterised in that each
The modified and blend step of component is as follows：First it is the synthesis of a components, by chloridized polyolefin, vinyl monomer and contains insatiable hunger
Mix according to certain ratio with the silane coupler 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 dispersion
Uniformly, other two kinds of silane couplers are separately added into afterwards, remaining alcohols solvent is added, and sealing places 10 after stirring
Remove the gas discharge that sealing will react generation after it.
Corresponding Heat vulcanization adhesive adhesive rubber species of the invention is extensive, from nitrile rubber, neoprene, butylbenzene rubber
Glue, natural rubber, butadiene rubber, butyl rubber and ethylene propylene diene rubber；The species for being bonded base material has iron, steel, aluminium, magnesium, pottery
Porcelain, fiber etc..
Specific embodiment
The present invention is further illustrated with case study on implementation below, but the present invention is not limited to these cases.
In each embodiment, the consumption of each component is referred both to " weight portion ", and the bonding strength (MPa) is by GB/T7760-
2003 determine；
In order to make sample, with tetrachloro-ethylene steam by by the steel disc degreasing of blasting treatment, and drying.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 sheet materials 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 to be bonded on rubber, leaves that 25mm is long and center 25mm ± 0.5mm wide
Region is providing on rubber.Then the steel disc is coated the adhesive of the thick example 1-9 of about 1um.
The natural rubber elastomeric compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.According to GB/T776-2003 vulcanized rubbers or the measure of thermoplastic elastomer and hard plate material bonding strength after heat cure bonding
Detected, the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
The ethylene propylene diene rubber elastomeric compound that DCP vulcanizes is placed on each test specimen, and the sulphur under 180 DEG C, the pressure of 10MPa
Change 10 minutes.According to GB/T776-2003 vulcanized rubbers or thermoplastic elastomer and hard plate material bonding strength after heat cure bonding
Measure is detected that 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 sheet materials when suitably thicken, the width of galvanized sheet
Spend for 25mm ± 0.5mm length is 60mm ± 1mm.Apply adhesive before, cover galvanized sheet test specimen two ends 17.5mm and
17.5mm, to prevent the region to can be used to be bonded on rubber, leaves that 25mm is long and central area 25mm ± 0.5mm wide is to carry
It is supplied on rubber.Then the galvanized sheet is coated the adhesive of the thick example 1-9 of about 1um.
The natural rubber elastomeric compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.According to GB/T776-2003 vulcanized rubbers or the measure of thermoplastic elastomer and hard plate material bonding strength after heat cure bonding
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 that 25mm ± 0.5mm is long
It is 60mm ± 1mm to spend.Before adhesive is applied, the 17.5mm and 17.5mm of alumina ceramic plate test specimen two ends are covered, in case
Only the region can be used to be bonded on rubber, leave that 25mm is long and central area 25mm ± 0.5mm wide is to provide on rubber.
Then the galvanized sheet is coated the adhesive of the thick example 1-9 of about 1um.
The natural rubber elastomeric compound of sulfur cross-linking is placed on each test specimen, and vulcanizes 6 under 150 DEG C, the pressure of 10MPa
Minute.According to GB/T776-2003 vulcanized rubbers or the measure of thermoplastic elastomer and hard plate material bonding strength after heat cure bonding
Detected, the rubber that Failure type record remains in bonded areas retains ratio.Gained test result is as follows:
Claims (10)
1. a kind of Heat vulcanization adhesive of novel silane coupler base, it is characterised in that composition includes：
Component a：A kind of formula is Resin-g-R1SiR3Olefin-containing functional group modified silane coupler；
Component b：A kind of formula is R2SiR3The modified silane coupler containing sulfydryl；
Component c：A kind of formula is R3Si-(OOR4)3The modified silane coupler containing peroxy；
Component d：Alcohols solvent；
In above-mentioned each formula, R is selected from the one kind in the alkoxy of halogen, acetoxyl group, 1-5 carbon atom；R1It is alkylene；R2
It is the sulfydryl of big molecular modification；R3It is alkylene；R4It is tertiary butyl or the tert-butyl group；Resin is halogenated polyolefin.
2. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that described R is 1-5
The alkoxy of individual carbon atom.
3. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that described R1It is 2-8
The double bond containing alkylene of individual carbon atom, described R2It is the 3-5 sulfydryl of carbon atom, described R3It is containing for 2-8 carbon atom
The alkylene of double bond.
4. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that the component a by
Including containing R1The raw material of unmodified silane coupler prepare, it is described containing R1Unmodified silane coupler be selected from pi-allyl
In trimethoxy silane, allyltriethoxysilane, vinyltrimethoxy silane, VTES one
Kind.
5. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that the component b by
Including containing R2The raw material of unmodified silane coupler prepare, it is described containing R2Unmodified silane coupler be selected from γ-mercapto third
Base trimethoxy silane, γ-thiocyanatopropyltriethoxysilane, double (triethoxy silicon substrate propyl group) tetrasulfides, double (three second
Epoxide silicon substrate propyl group) one kind in disulphide.
6. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that the component c by
Including containing R3The raw material of unmodified silane coupler prepare, it is described containing R3Unmodified silane coupler be selected from vinyl
Tri-tert peroxy-silane, the tert-butylperoxy base silane of methyl three, vinyl methyl ethyl tert-butylperoxy base silane, vinyl
One kind in three tert-butylperoxy silane.
7. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that described halogenation gathers
Alkene is selected from chlorinated natural rubber, chlorosulfonated polyethylene, haloflex, chlorinated polypropylene, modified chlorinated polypropylene, chlorination second
One or more in alkene-propylene copolymer, ethylene chloride-ethylene acetate copolymer, propylene dichloride -2- butylene copolymers.
8. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that by weight,
The each group distribution ratio is as follows：
9. the Heat vulcanization adhesive of novel silane coupler base as claimed in claim 1, it is characterised in that described component a
Gather selected from halogenated polyolefin grafting allyltrimethoxysilanis, halogenated polyolefin grafting allyltriethoxysilane, halogenation
One kind in alkene grafting vinyl trimethoxy silane, halogenated polyolefin grafting vinyl triethoxysilane；Described group
B is divided to be selected from γ-mercaptopropyl trimethoxysilane, γ-thiocyanatopropyltriethoxysilane, double (triethoxy silicon substrate propyl group) four
One kind in sulfide, double (triethoxy silicon substrate propyl group) disulphide；Described component c is selected from vinyl tri-tert peroxide
Silane, the tert-butylperoxy base silane of methyl three, vinyl methyl ethyl tert-butylperoxy base silane, the tert-butylperoxy of vinyl three
One kind in silane.
10. the Heat vulcanization adhesive of a kind of novel silane coupler base as described in any one of claim 1-9 claim
Preparation method, it is characterised in that comprise the following steps：Synthesis component a, component a and constituent part d is mixed, finally
Component b, component c are mixed into, remaining ingredient d is blended into, 50 degrees Celsius of sealings are placed 10 days, sealed again after deflation, obtain final product.
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| 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 |
| CN112680179A (en) * | 2020-12-25 | 2021-04-20 | 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 |
| 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 |
| CN113698265A (en) * | 2021-02-09 | 2021-11-26 | 北京理工大学 | Adhesive based on self-sustaining reaction safe and environment-friendly firework propellant |
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|---|---|
| CN106753060B (en) | 2018-04-17 |
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