CN1710007A - Room temperature solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive - Google Patents
Room temperature solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive Download PDFInfo
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- CN1710007A CN1710007A CN200510040945.7A CN200510040945A CN1710007A CN 1710007 A CN1710007 A CN 1710007A CN 200510040945 A CN200510040945 A CN 200510040945A CN 1710007 A CN1710007 A CN 1710007A
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- temperature
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- solidifed
- vulcanizing
- self
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- 239000004593 Epoxy Substances 0.000 title claims description 21
- 230000001070 adhesive effect Effects 0.000 title claims description 14
- 239000000853 adhesive Substances 0.000 title claims description 12
- KVNRLNFWIYMESJ-UHFFFAOYSA-N butyronitrile Chemical compound CCCC#N KVNRLNFWIYMESJ-UHFFFAOYSA-N 0.000 title claims description 11
- 239000007822 coupling agent Substances 0.000 claims abstract description 12
- 239000007788 liquid Substances 0.000 claims abstract description 8
- 150000004985 diamines Chemical class 0.000 claims abstract description 7
- 239000003822 epoxy resin Substances 0.000 claims abstract description 5
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 5
- 229920013649 Paracril Polymers 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 7
- 229920005989 resin Polymers 0.000 claims description 7
- 239000011347 resin Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 239000000945 filler Substances 0.000 claims description 5
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 claims description 4
- FUIQBJHUESBZNU-UHFFFAOYSA-N 2-[(dimethylazaniumyl)methyl]phenolate Chemical compound CN(C)CC1=CC=CC=C1O FUIQBJHUESBZNU-UHFFFAOYSA-N 0.000 claims description 4
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 claims description 4
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- 239000005995 Aluminium silicate Substances 0.000 claims description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 3
- 235000012211 aluminium silicate Nutrition 0.000 claims description 3
- 239000004148 curcumin Substances 0.000 claims description 3
- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 claims description 3
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 claims description 3
- XZZNTLNFQVAKFD-UHFFFAOYSA-N 1,3-diethyl-2-methylbenzene Chemical compound CCC1=CC=CC(CC)=C1C XZZNTLNFQVAKFD-UHFFFAOYSA-N 0.000 claims description 2
- JRLPEMVDPFPYPJ-UHFFFAOYSA-N 1-ethyl-4-methylbenzene Chemical compound CCC1=CC=C(C)C=C1 JRLPEMVDPFPYPJ-UHFFFAOYSA-N 0.000 claims description 2
- HWRRQRKPNKYPBW-UHFFFAOYSA-N 2,4-dimethylcyclohexan-1-amine Chemical compound CC1CCC(N)C(C)C1 HWRRQRKPNKYPBW-UHFFFAOYSA-N 0.000 claims description 2
- CBEVWPCAHIAUOD-UHFFFAOYSA-N 4-[(4-amino-3-ethylphenyl)methyl]-2-ethylaniline Chemical compound C1=C(N)C(CC)=CC(CC=2C=C(CC)C(N)=CC=2)=C1 CBEVWPCAHIAUOD-UHFFFAOYSA-N 0.000 claims description 2
- NFVPEIKDMMISQO-UHFFFAOYSA-N 4-[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC=C(O)C=C1 NFVPEIKDMMISQO-UHFFFAOYSA-N 0.000 claims description 2
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 claims description 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims description 2
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 claims description 2
- 235000012204 lemonade/lime carbonate Nutrition 0.000 claims description 2
- QAZHYRJYZIMJJI-UHFFFAOYSA-N n-ethylpiperazin-1-amine Chemical compound CCNN1CCNCC1 QAZHYRJYZIMJJI-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- ZTFZSHLWORMEHO-UHFFFAOYSA-A pentaaluminum;[oxido(phosphonatooxy)phosphoryl] phosphate Chemical compound [Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O.[O-]P([O-])(=O)OP([O-])(=O)OP([O-])([O-])=O ZTFZSHLWORMEHO-UHFFFAOYSA-A 0.000 claims description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 claims description 2
- 235000015320 potassium carbonate Nutrition 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 229920000459 Nitrile rubber Polymers 0.000 abstract description 5
- 150000001412 amines Chemical class 0.000 abstract description 2
- IRLQAJPIHBZROB-UHFFFAOYSA-N buta-2,3-dienenitrile Chemical compound C=C=CC#N IRLQAJPIHBZROB-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 229910000831 Steel Inorganic materials 0.000 description 4
- 229920006332 epoxy adhesive Polymers 0.000 description 4
- 239000010959 steel Substances 0.000 description 4
- DSROZUMNVRXZNO-UHFFFAOYSA-K tris[(1-naphthalen-1-yl-3-phenylnaphthalen-2-yl)oxy]alumane Chemical compound C=1C=CC=CC=1C=1C=C2C=CC=CC2=C(C=2C3=CC=CC=C3C=CC=2)C=1O[Al](OC=1C(=C2C=CC=CC2=CC=1C=1C=CC=CC=1)C=1C2=CC=CC=C2C=CC=1)OC(C(=C1C=CC=CC1=C1)C=2C3=CC=CC=C3C=CC=2)=C1C1=CC=CC=C1 DSROZUMNVRXZNO-UHFFFAOYSA-K 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- KWYHDKDOAIKMQN-UHFFFAOYSA-N N,N,N',N'-tetramethylethylenediamine Chemical compound CN(C)CCN(C)C KWYHDKDOAIKMQN-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000012764 mineral filler Substances 0.000 description 2
- 229910052755 nonmetal Inorganic materials 0.000 description 2
- 230000003014 reinforcing effect Effects 0.000 description 2
- -1 siloxanes Chemical class 0.000 description 2
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000005336 cracking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000010008 shearing Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
Abstract
This is room temperature solidified nitrile-butadiene rubber (NBR) of wide temperature area, high intensity and high toughness. It has excellent extensibility, caking intensity, water insistence and oil insistence at -60 - 100 Deg. C wide temperature area. Components A are amine terminated butadiene nitrile rubber (ATBN), liquid state diamine, promoter and coupling agent; Components B are epoxy resin, coupling agent, and inorganic mixed padding. When used, presently mix and felt the sealed Components A and Components B at room temperature according to 1 : 1 - 1: 2.2 weight proportion, and solidified for 3 - 7 days at room temperature.
Description
(1) invention field
The present invention relates to adhesive area.This tackiness agent is that the wide temperature of self-vulcanizing territory high-strength high-toughness epoxy strengthens paracril, have outstanding unit elongation, bond strength, outstanding water-fast, oil-proofness in-60～100 ℃ of wide temperature territories, be applied to metal-metal, metals-nonmetal, nonmetal-nonmetallic bonding such as some aviations, boats and ships, automobile.
(2) background technology
Resins, epoxy is that as the shortcoming of structural tackiness agent its fragility is bigger, and have shrinkability at solidification process, produce bigger internal stress, for this reason, people take toughness reinforcing epoxy adhesive with elastomerics very early, to improve the adhesiveproperties and the resistance to impact shock of epoxy adhesive.As with nbr carboxyl terminal (CN 87100265A), distolateral basic carboxy nitrile rubber (United States Patent (USP) 3,894,112; United States Patent (USP) 3,894,112; ) next epoxy resin toughened.The above-mentioned paracril of result often is distributed in the epoxy external phase with particle (disperse phase), forms " island " structure, can improve the toughness of epoxy adhesive to a certain extent.
Yet in some actual application, for the situation that is occurred deformation by sticking part, as when by the thermal expansivity difference of sticking part, even when differing big, temperature sharply changes can produce distortion; Or when the soft durometer of being glued part was relatively large, bigger ambient pressure changed to produce too and is out of shape, and the general toughness reinforcing requirement that can't satisfy than large deformation often causes stress cracking.
Deficiency at existing epoxy adhesive existence, the object of the present invention is to provide a kind of self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive, its structure is that two-phase is continuous altogether, can and solidify in the operation of room temperature bonding, is applied to easy deformation member in-60 ℃～100 ℃ wide temperature territories.
(3) content of the present invention
The present invention has prepared a kind of self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive, utilize epoxy group(ing) and amido self cure characteristic but the invention reside in, with Resins, epoxy and the self cure of end amido paracril (ATBN), and introducing liquid diamine, and promotor, the epoxy for preparing wide temperature territory high-strength and high ductility strengthens butadiene-acrylonitrile rubber.
The present invention implements like this: be mixed into the A component with end amido paracril, liquid diamine, promotor, coupling agent by certain proportioning; Be mixed into the B component with Resins, epoxy, coupling agent and mixing mineral filler by certain proportioning; During use by A: B is that 1: 1～1: 2.2 weight ratio hybrid modulation gets final product.
The present invention fills a prescription as follows: (in unit weight part)
The A component:
End amido paracril 80～180 weight parts
Liquid diamine 1.5～25 weight parts
Promotor 0～8 weight part
Coupling agent 0～10 weight part
The B component:
Resins, epoxy 100 weight parts
Coupling agent 0～10 weight part
Mixed fillers 50～150 weight parts
A, B component with encapsulation during use bond self-vulcanizing 3-7 days by 1: 1～1: 2.2 weight ratio in the room temperature field mix.
Resins, epoxy is bisphenol A type epoxy resin, as E-51, E44.
End amido paracril (ATBN) number-average molecular weight 1000～4000, acrylonitrile content 16%-28%.
Promotor is 2,4,6, one three (dimethylamino methyl)-phenol (DMP-30), 2-(dimethylamino methyl) phenol (DMP-10), N, N, N, N-Tetramethyl Ethylene Diamine (TMEDA), triethylamine (TEA).
Liquid diamine is 2,4 and 2,6 diethyl toluene diamine mixtures (E100), m-xylene diamine (m-XAD), N-ethylamino-piperazine (NEP), isophorone diamine (IPDA), two (4-amino-3-methylcyclohexyl) methane (Laromin C-260).
Coupling agent is the siloxanes that has different functional groups, for example γ-glycidyl ether oxygen base propyl trimethoxy silicane (KH560), γ-An Bingjisanjiayangjiguiwan (KH550).
The mixing mineral filler is talcum powder, lime carbonate, kaolin, super-fine zinc dust, salt of wormwood whisker, aluminium triphosphate, red iron oxide mixed fillers.
Experiment shows, adopts the application temperature territory broad (60～100 ℃) of the tackiness agent of technical scheme preparation of the present invention, and adaptability is stronger.Have 3%～10% unit elongation, shear strength 40～60MPa in the time of-60 ℃, have 30～50% elongation at break, the shear strength of 5～10MPa in the time of 100 ℃.Tackiness agent of the present invention in addition has excellent water-fast, oil resistance, and steel to steel, steel are had good adhesiveproperties to rubber, steel to plastics etc., is applicable to metal-metal, metals-nonmetal, nonmetal-nonmetallic bonding such as aviation, boats and ships, automobile.
(4) embodiment
The prescription of table 1 specific embodiment of the invention (weight part)
| Example one | Example two | Example three | Example four | ||
| The A component | ATBN liquid two amine promoter coupling agents | ?90 ?25(E100) ?4(DMP-30) ?8(KH550) | ??109 ??20 ??2(DMP-30) ??0 | ??120 ??15 ??0 ??6(KH560) | ??180 ??10 ??0 ??4(KH560) |
| The B component | Epoxy resin coupling agent talcum powder calcium carbonate kaolin super-fine zinc dust aluminium triphosphate potassium oxide whisker iron oxide red | ?100(E-44) ?0 ?10 ?10 ?10 ?50 ?50 ?20 ?0 | ??100(E-51) ??6(KH560) ??25 ??25 ??25 ??0 ??0 ??20 ??15 | ??100(E-51) ??0 ??20 ??20 ??20 ??0 ??0 ??15 ??15 | ??100(E-51) ??0 ??20 ??20 ??20 ??0 ??10 ??20 ??0 |
| Proportioning | ??A∶B | ?1∶2 | ??1∶1.6 | ??1∶1.3 | ??1∶1 |
The Mechanics Performance Testing result of table 2 specific embodiment of the invention
| Mechanical property | Example 1 | Example 2 | Example 3 | Example 4 | ||||
| Body breaking tenacity MPa | ?-25℃ ???23℃ ??100℃ | ??28.6 ??16.8 ??8.6 | ?-25℃ ???23℃ ??100℃ | ??24.3 ??13.4 ??5.9 | ?-60℃ ???23℃ ??100℃ | ??41.0 ??13.1 ??4.9 | ?-60℃ ???23℃ ??100℃ | ??37.0 ??11.1 ??4.5 |
| Body tensile yield % | ?-25℃ ???23℃ ??100℃ | ??5.6 ??20.9 ??43.8 | ?-25℃ ???23℃ ??100℃ | ??16.1 ??29.4 ??49.3 | ?-60℃ ???23℃ ??100℃ | ??5.1 ??36.4 ??48.3 | ?-60℃ ???23℃ ??100℃ | ??6.7 ??38.4 ??49.3 |
| Bonding shearing resistance MPa | ?-25℃ ???23℃ ??100℃ | ??29.0 ??18.4 ??11.1 | ?-25℃ ???23℃ ??100℃ | ??26.0 ??18.1 ??8.0 | ?-60℃ ???23℃ ??100℃ | ??42 ??14.8 ??6.2 | ?-60℃ ???23℃ ??100℃ | ??39.2 ??12.6 ??5.8 |
Claims (7)
1, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive is characterized in that tackiness agent of the present invention is made of two kinds of components of A, B, and two kinds of components are composed as follows in unit weight part:
The A component:
End amido paracril 80～180 weight parts
Liquid diamine 1.5～25 weight parts
Promotor 0～8 weight part
Coupling agent 0～10 weight part
The B component:
Resins, epoxy 100 weight parts
Coupling agent 0～10 weight part
Inorganic mixed fillers 50～150 weight parts
A, B component bond self-vulcanizing 3-7 days by 1: 1～1: 2.2 weight ratio in the room temperature field mix.
2, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1 is characterized in that holding the number-average molecular weight 1000-4000 of amido paracril, acrylonitrile content 16%-28%.
3, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1 is characterized in that promotor is 2,4,6, one three (dimethylamino methyl)-phenol (DMP-30), 2-(dimethylamino methyl) phenol (DMP-10).
4, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1, it is characterized in that liquid diamine is 2,4 and 2,6 diethyl toluene diamine mixtures (E100), m-xylene diamine (m-XAD), N-ethylamino-piperazine (NEP), isophorone diamine (IPDA), two (4-amino-3-methylcyclohexyl) methane (Laromin C-260).
5, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1 is characterized in that coupling agent is γ-glycidyl ether oxygen base propyl trimethoxy silicane (KH560), γ-An Bingjisanjiayangjiguiwan (KH550).
6, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1 is characterized in that Resins, epoxy is bisphenol A type epoxy resin.
7, self-vulcanizing solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive according to claim 1 is characterized in that inorganic mixed fillers is talcum powder, lime carbonate, kaolin, super-fine zinc dust, salt of wormwood whisker, aluminium triphosphate, red iron oxide mixed fillers.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510040945.7A CN1710007A (en) | 2005-07-08 | 2005-07-08 | Room temperature solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN200510040945.7A CN1710007A (en) | 2005-07-08 | 2005-07-08 | Room temperature solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN1710007A true CN1710007A (en) | 2005-12-21 |
Family
ID=35706297
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN200510040945.7A Pending CN1710007A (en) | 2005-07-08 | 2005-07-08 | Room temperature solidifed wide-temperature-range high-strength high-toughness epoxy reinforced butyronitrile adhesive |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN1710007A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265400B (en) * | 2008-05-10 | 2011-12-21 | 大连理工大学 | Room temperature controllable curing building adhesive and preparation method thereof |
| CN101358121B (en) * | 2008-09-10 | 2012-05-09 | 武汉科技学院 | Preparation method of high temperature resistant epoxy adhesive capable of room temperature curing |
| CN103374320A (en) * | 2013-06-17 | 2013-10-30 | 南京大学 | Method for toughening and curing epoxy resin adhesive by using amino-terminated liquid nitrile rubber |
| CN104109296A (en) * | 2014-07-14 | 2014-10-22 | 宁国市日格美橡塑制品有限公司 | Water-tolerant oil-resistant rubber material |
| CN104293264A (en) * | 2014-09-17 | 2015-01-21 | 明光市锐创电气有限公司 | High-strength metal glue |
| CN108626290A (en) * | 2018-05-04 | 2018-10-09 | 南京大学 | A kind of enhancing damping-constraining device |
| CN109415540A (en) * | 2016-06-30 | 2019-03-01 | 米其林集团总公司 | Rubber composition comprising epoxy resin and specific amine hardener |
-
2005
- 2005-07-08 CN CN200510040945.7A patent/CN1710007A/en active Pending
Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN101265400B (en) * | 2008-05-10 | 2011-12-21 | 大连理工大学 | Room temperature controllable curing building adhesive and preparation method thereof |
| CN101358121B (en) * | 2008-09-10 | 2012-05-09 | 武汉科技学院 | Preparation method of high temperature resistant epoxy adhesive capable of room temperature curing |
| CN103374320A (en) * | 2013-06-17 | 2013-10-30 | 南京大学 | Method for toughening and curing epoxy resin adhesive by using amino-terminated liquid nitrile rubber |
| CN104109296A (en) * | 2014-07-14 | 2014-10-22 | 宁国市日格美橡塑制品有限公司 | Water-tolerant oil-resistant rubber material |
| CN104293264A (en) * | 2014-09-17 | 2015-01-21 | 明光市锐创电气有限公司 | High-strength metal glue |
| CN109415540A (en) * | 2016-06-30 | 2019-03-01 | 米其林集团总公司 | Rubber composition comprising epoxy resin and specific amine hardener |
| CN109415540B (en) * | 2016-06-30 | 2021-09-10 | 米其林集团总公司 | Rubber composition comprising an epoxy resin and a specific amine hardener |
| US11499036B2 (en) | 2016-06-30 | 2022-11-15 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising an epoxide resin and a specific amine hardener |
| CN108626290A (en) * | 2018-05-04 | 2018-10-09 | 南京大学 | A kind of enhancing damping-constraining device |
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