CN102964778A - Preparation method of ionic liquid-epoxy resin composite material - Google Patents
Preparation method of ionic liquid-epoxy resin composite material Download PDFInfo
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- CN102964778A CN102964778A CN2012105186629A CN201210518662A CN102964778A CN 102964778 A CN102964778 A CN 102964778A CN 2012105186629 A CN2012105186629 A CN 2012105186629A CN 201210518662 A CN201210518662 A CN 201210518662A CN 102964778 A CN102964778 A CN 102964778A
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- ionic liquid
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- 239000002131 composite material Substances 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 19
- 239000004850 liquid epoxy resins (LERs) Substances 0.000 title claims abstract description 12
- 239000003822 epoxy resin Substances 0.000 claims abstract description 27
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 27
- 239000002608 ionic liquid Substances 0.000 claims abstract description 23
- 229910052625 palygorskite Inorganic materials 0.000 claims abstract description 21
- 239000011159 matrix material Substances 0.000 claims abstract description 15
- 239000000654 additive Substances 0.000 claims abstract description 5
- 230000002195 synergetic effect Effects 0.000 claims abstract description 5
- 238000012545 processing Methods 0.000 claims abstract description 4
- 229920005989 resin Polymers 0.000 claims description 32
- 239000011347 resin Substances 0.000 claims description 32
- 239000004593 Epoxy Substances 0.000 claims description 31
- 238000003756 stirring Methods 0.000 claims description 19
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 14
- 239000003795 chemical substances by application Substances 0.000 claims description 8
- CAWGQUPKYLTTNX-UHFFFAOYSA-N 3,4,5,6-tetrahydro-2,7-benzodioxecine-1,8-dione Chemical group O=C1OCCCCOC(=O)C2=CC=CC=C12 CAWGQUPKYLTTNX-UHFFFAOYSA-N 0.000 claims description 7
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 claims description 7
- -1 1-octyl Chemical group 0.000 claims description 6
- 150000001875 compounds Chemical class 0.000 claims description 5
- SFPTVQNKTCPLAX-UHFFFAOYSA-N 3-ethyl-1-methyl-1,2-dihydroimidazol-1-ium;2,2,2-trifluoroacetate Chemical compound [O-]C(=O)C(F)(F)F.CC[NH+]1CN(C)C=C1 SFPTVQNKTCPLAX-UHFFFAOYSA-N 0.000 claims description 3
- JMNFVQWMBCLWAS-UHFFFAOYSA-N C(F)(F)F.C(C)N1CN(C=C1)C Chemical compound C(F)(F)F.C(C)N1CN(C=C1)C JMNFVQWMBCLWAS-UHFFFAOYSA-N 0.000 claims description 3
- JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 claims description 3
- AYMDKQQFUZHWGX-UHFFFAOYSA-N 1-ethyl-3-methyl-1,2-dihydroimidazol-1-ium;thiocyanate Chemical compound [S-]C#N.CC[NH+]1CN(C)C=C1 AYMDKQQFUZHWGX-UHFFFAOYSA-N 0.000 claims description 2
- 239000012895 dilution Substances 0.000 claims description 2
- 238000010790 dilution Methods 0.000 claims description 2
- 235000013399 edible fruits Nutrition 0.000 claims description 2
- 238000010438 heat treatment Methods 0.000 claims description 2
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims description 2
- 238000003860 storage Methods 0.000 claims description 2
- 239000000463 material Substances 0.000 abstract description 11
- 230000001976 improved effect Effects 0.000 abstract description 6
- 238000005452 bending Methods 0.000 abstract description 2
- 238000013329 compounding Methods 0.000 abstract 2
- 230000000996 additive effect Effects 0.000 abstract 1
- 239000004927 clay Substances 0.000 abstract 1
- 238000012360 testing method Methods 0.000 description 16
- 238000005299 abrasion Methods 0.000 description 11
- 230000035939 shock Effects 0.000 description 11
- 238000005303 weighing Methods 0.000 description 6
- 238000005516 engineering process Methods 0.000 description 3
- 238000003754 machining Methods 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 230000001070 adhesive effect Effects 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 125000003700 epoxy group Chemical group 0.000 description 2
- 239000000945 filler Substances 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- IBZJNLWLRUHZIX-UHFFFAOYSA-N 1-ethyl-3-methyl-2h-imidazole Chemical compound CCN1CN(C)C=C1 IBZJNLWLRUHZIX-UHFFFAOYSA-N 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000001449 anionic compounds Chemical group 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000012777 electrically insulating material Substances 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000006872 improvement Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 238000005342 ion exchange Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000011068 loading method Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 229910052755 nonmetal Inorganic materials 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002892 organic cations Chemical class 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 238000004537 pulping Methods 0.000 description 1
- 230000002787 reinforcement Effects 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 238000001132 ultrasonic dispersion Methods 0.000 description 1
- 230000003245 working effect Effects 0.000 description 1
Landscapes
- Epoxy Resins (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
The invention provides a preparation method of an ionic liquid epoxy resin composite material, which is obtained by compounding epoxy resin serving as a matrix and palygorskite clay and ionic liquid serving as a synergistic additive. The palygorskite can effectively improve the mechanical property, the processing property and the wear resistance of the material due to the special structure; the ionic liquid is added, so that the wear resistance of the epoxy resin is better improved, the impact resistance is better improved, the bending strength of the epoxy resin is less influenced, and the ionic liquid-epoxy resin composite material formed by compounding has good comprehensive performance, so that the application of the epoxy resin is expanded.
Description
Technical field
The invention belongs to technical field of composite materials, relate to a kind of preparation method of epoxy resin composite material, relate in particular to a kind of preparation method of ionic liquid-epoxy resin composite material.
Background technology
Resins, epoxy refers to contain in the molecule resin of two or more epoxy group(ing), it is to carry out the thermoplastic polymer performed polymer that polycondensation generates by the compound with epoxy group(ing) and multi-hydroxy compound, it is a kind of active intermediate for the production of interchangeable heat solidity superpolymer, so owing to various metals and most of nonmetal laudatory title that has good bonding strength that " multi-purpose adhesive " arranged, be widely used in the fields such as coating, matrix material high-performance adhesive, electrically insulating material, civil construction.But since its solidify after cross-linking density high, cause that internal stress is large, matter is crisp, and poor heat resistance, the high deficiency of frictional coefficient and limited the further application of Resins, epoxy.
Along with the high speed development of modernization industry, more and more higher requirement has been proposed for the performance of material.The high performance of low-cost realization material is the advanced subject of material scientific research and application, and realizes that the high performance of Resins, epoxy generally has two approach, the one, and development of new Resins, epoxy; The 2nd, adopt copolymerization/blending method that existing Resins, epoxy is carried out modification.The former is longer research cycle, need to expend a large amount of human and material resources, thereby the copolymerization/blending and modifying of Resins, epoxy is the important means that realizes this resin high performance always.By selecting different solidifying agent, filler and other auxiliary agent, make Resins, epoxy obtain the specific performance of various needs, thereby greatly opened up the range of application of Resins, epoxy.
The molecular characterization of macromolecular material uniqueness makes it have certain advantage aspect tribological property.The particle diameter of nanoparticle is within lnm ~ 100nm, and is little for size of particles, and surperficial non-matching atom is many, large with polymkeric substance generation physics or chemically combined possibility.By the dispersion of meticulous control nano material in superpolymer and compound, can in the weak microcell of resin, play reinforcement, fill, strengthen interface interaction power, reduce the effect of free volume, only just can in a sizable scope, effectively improve the over-all properties of matrix material with a small amount of inorganic particulate, not only play enhancing, toughness reinforcing effect, also can not reduce other performance of material.Palygorskite is a kind of natural monodimension nanometer material mineral, have special fibrous crystalline structure and the performances such as good adsorptivity, rheological, catalytic, fillibility and ion-exchange, thermally-stabilised, anti-salt, gel, pulping and high-temperature phase-change, make its application prospect boundless.
Chinese patent CN102504672A discloses a kind of epoxy resin-based wear-resistant anticorrosive material, as matrix take Resins, epoxy, take nanometer palygorskite-aluminum oxide as filler, adopt ultra-sonic dispersion and mechanical blending technology to be prepared from, has excellent wear-and corrosion-resistant performance, and has good sticking power, therefore, can be used as compound coating and be applied in the component of machine material surface, improving the wear-and corrosion-resistant performance of component of machine, thereby prolong work-ing life of metallic element, but owing to use aluminum oxide to be synergist, its complicated process of preparation, although improve the wear resistance of epoxy resin-matrix, bad to resistance to impact shock and the flexural strength improved effect of epoxy resin-matrix.
Summary of the invention
The objective of the invention is for problems of the prior art, a kind of preparation method with ionic liquid-epoxy resin composite material of good abrasion resistance and resistance to impact shock is provided.
The preparation method of ionic liquid epoxy resin composite material of the present invention is take Resins, epoxy as matrix, and is compound and get as synergistic additives with palygorskite, ionic liquid.Its concrete preparation technology is as follows:
With Resins, epoxy heating liquefaction, after the thinner dilution, add toughner, after stirring, add palygorskite, ionic liquid, mix, Fruit storage adds solidifying agent, stir, again vacuumize processing, reverse mould solidifies 12 ~ 24h and both got in 50 ~ 70 ℃ of baking ovens.
Described ionic liquid is that described ionic liquid is 1-octyl group-3 methyl imidazolium tetrafluoroborate, 1-ethyl-3 methyl imidazolium tetrafluoroborate, 1-ethyl-3-methylimidazole thiocyanate-, 1-ethyl-3-methylimidazole trifluoroacetate or 1-ethyl-3-methylimidazole fluoroform sulphonate.The consumption of ionic liquid is 1 ~ 9% of Resins, epoxy quality.
The granularity of described palygorskite is 20nm ~ 100nm.The consumption of palygorskite is 1 ~ 9% of Resins, epoxy quality.
Described thinner is the mixed solution that is formed with the volume ratio of 1:2 ~ 1:4 by dimethylbenzene and propyl carbinol.
Described toughner is butylene phthalate, and its add-on is 0.2 ~ 0.8% of Resins, epoxy quality.The present invention is take Resins, epoxy as matrix, to utilize palygorskite and ionic liquid as synergistic additives: polygorskite since its special structure can the Effective Raise material mechanical property, processing characteristics and wear resisting property; Ionic liquid is called again the room temperature melting salt, be under room temperature and adjacent temperature fully by nitrogenous, the organic cation of phosphorus and the organic liquid that inorganic anion forms, its almost do not have vapour pressure, non-volatile, colourless odorless, have a preferably chemical stability.The adding of ionic liquid not only has preferably improvement to the wear resisting property of Resins, epoxy, and resistance to impact shock there is good improved effect, less on the flexural strength impact of Resins, epoxy simultaneously, thereby the ionic liquid-epoxy resin composite material that is composited as synergistic additives with palygorskite and ionic liquid has good over-all properties, thereby expanded the application of Resins, epoxy.
Below by concrete experiment wear resisting property and the machining property of Resins, epoxy/palygorskite of the present invention/carbon-fibre composite are measured.
1, rub and examine coefficient test: carry out friction-wear test at the UMT-3MT frictional testing machines, loading force is 50N, and frequency is 3.3HZ, stroke 3mm, and antithesis Φ 10mm, test duration 10min, directly obtaining rubs examines coefficient.
Test result: along with the increase of polygorskite content, the average friction coefficient of matrix material reduces; Along with the increase of ionic liquid content, the average friction coefficient of matrix material increases.When the add-on of palygorskite is 1 ~ 9%, when the add-on of ionic liquid is 1 ~ 9%, the average friction coefficient of matrix material is 0.09049～0.21356, and its frictional behaviour is than pure epoxy resin all be significantly improved (average friction coefficient of pure epoxy resin is 0.22802).
1.2 abrasion loss test: claim its quality with the rigorous analysis balance to the preparation sample respectively before and after rub(bing)test, its mean value is got in each weighing 5 times, relatively the average abrasion amount.
Test result: the average abrasion amount of epoxy resin composite material is 0.00015g ~ 0.01012g.The abrasion loss of epoxy resin composite material has had than pure epoxy resin and has reduced significantly that (abrasion loss of pure epoxy resin is 0.00126g.）
2. machining property
2.1 shock resistance: according to GB " GB/T 2571-1995 " matrix material is prepared the batten of 80mm * 10mm * 4mm, carry out the shock resistance test.
Test result: average impact resistance can be 49.7 ~ 149.6J/m, relative pure epoxy resin, the resistance to impact shock that has improved 0.93 ~ 203.98%(pure epoxy resin is 49.2J/m).
2.2 flexural strength: the batten that matrix material is prepared 80mm * 10mm * 6mm according to GB " GB/T 2571-1995 ", carry out the bending resistance test, flexural strength is 44.6～68.8Mpa, and pure epoxy resin affects little (the pure epoxy resin flexural strength is 63.8Mpa) relatively.
Comprehensive above-mentioned all kinds of performances, the addition that the present invention chooses palygorskite is 1% ~ 9%, when the addition of ionic liquid was 1% ~ 9%, the antiwear epoxy resin matrix material that obtains had good machining property and wear resistance.
Embodiment
Describe below by the preparation and property of specific embodiment to ionic liquid epoxy resin composite material of the present invention.
Embodiment 1
Take by weighing in the round-bottomed flask that 5g Resins, epoxy is positioned over 50mL, place 50 ℃ of oil baths to liquefy.Add thinner (dimethylbenzene 0.15mL, propyl carbinol 0.60mL), stir 10min; Then add butylene phthalate 0.027mL, stir 10min; Add 0.05g 1-octyl group-3 methyl imidazolium tetrafluoroborate, 0.45g palygorskite (20nm ~ 100nm), stir 40min; Vacuumize 10min; Add T-31 solidifying agent 1.25g, vacuumize 2min, pour mould into, in 60 ℃ of baking ovens, solidify 24h, both got epoxy resin composite material.
The wear resisting property test: average friction coefficient is 0.09049, and the average abrasion amount is 0.00015g, and shock resistance intensity is 49.7J/m; Flexural strength is 44.6Mpa
Embodiment 2
Take by weighing in the round-bottomed flask that 5g Resins, epoxy is positioned over 50mL, place 50 ℃ of oil baths to liquefy.Add thinner (dimethylbenzene 0.25mL, propyl carbinol 0.50mL), stir 10min; Then add butylene phthalate 0.042 mL, stir 10min; Add 0.1g 1-ethyl-3 methyl imidazolium tetrafluoroborate, 0.4g palygorskite (20nm ~ 100nm), stir 40min; Vacuumize 10min; Add T-31 solidifying agent 1.25g, vacuumize 2min, pour mould into, in 60 ℃ of baking ovens, solidify 24h, both got epoxy resin composite material.
The wear resisting property test: average friction coefficient is 0.21356, and the average abrasion amount is 0.01012g, and shock resistance intensity is 149.6J/m; Flexural strength is 68.8Mpa.
Embodiment 3
Take by weighing in the round-bottomed flask that 5g Resins, epoxy is positioned over 50mL, place 50 ℃ of oil baths to liquefy.Add thinner (dimethylbenzene 0.17mL, propyl carbinol 0.58mL), stir 10min; Then add butylene phthalate 0.036 mL, stir 10min; 0.35g (20nm ~ 100nm), 0.15g 1-ethyl-3-methylimidazole thiocyanate-stirs 40min to palygorskite; Vacuumize 10min; Add T-31 solidifying agent 1.25g, vacuumize 2min, pour mould into, in 60 ℃ of baking ovens, solidify 24h, both got epoxy resin composite material.
The wear resisting property test: average friction coefficient is 0.1484, and the average abrasion amount is 0.01002g, and shock resistance intensity is 59.66J/m; Flexural strength is 56.1Mpa.
Embodiment 4 takes by weighing in the round-bottomed flask that 5g Resins, epoxy is positioned over 50mL, places 50 ℃ of oil baths to liquefy.Add thinner (dimethylbenzene 0.20mL, propyl carbinol 0.55mL), stir 10min; Then add butylene phthalate 0.012mL, stir 10min; Add 0.3g 1-ethyl-3-methylimidazole fluoroform sulphonate, and the 0.3g palygorskite (20 ~ 100nm), stir 40min; Vacuumize 10min; Add T-31 solidifying agent 1.25g, vacuumize 2min, pour mould into, in 60 ℃ of baking ovens, solidify 24h, both got epoxy resin composite material.
The wear resisting property test: average friction coefficient is 0.186, and the average abrasion amount is 0.0007, and shock resistance intensity is 58.1J/m; Flexural strength is 64.1Mpa.
Embodiment 5
Take by weighing in the round-bottomed flask that 5g Resins, epoxy is positioned over 50mL, place 50 ℃ of oil baths to liquefy.Add thinner (dimethylbenzene 0.22mL, propyl carbinol 0.53mL), stir 10min; Then add butylene phthalate 0.048mL, stir 10min; Add 0.05g 1-ethyl-3-methylimidazole trifluoroacetate, and the 0.45g palygorskite (20 ~ 100nm), stir 40min; Vacuumize 10min; Add T-31 solidifying agent 1.25g, vacuumize 2min, pour mould into, in 60 ℃ of baking ovens, solidify 24h, both got epoxy resin composite material.
The wear resisting property test: average friction coefficient is 0.1326, and the average abrasion amount is 0.00026g, and shock resistance intensity is 54.1856J/m, and flexural strength is 51.57Mpa.
Claims (8)
1. the preparation method of ionic liquid-epoxy resin composite material is take Resins, epoxy as matrix, and is compound and get as synergistic additives with palygorskite, ionic liquid.
2. the preparation method of ionic liquid-epoxy resin composite material as claimed in claim 1, it is characterized in that: described ionic liquid is 1-octyl group-3 methyl imidazolium tetrafluoroborate, 1-ethyl-3 methyl imidazolium tetrafluoroborate, 1-ethyl-3-methylimidazole thiocyanate-, 1-ethyl-3-methylimidazole trifluoroacetate or 1-ethyl-3-methylimidazole fluoroform sulphonate.
3. the preparation method of ionic liquid-epoxy resin composite material as claimed in claim 2, it is characterized in that: the consumption of described ionic liquid is 1 ~ 9% of Resins, epoxy quality.
4. the preparation method of ionic liquid-epoxy resin composite material as claimed in claim 1, it is characterized in that: the granularity of described palygorskite is 20nm ~ 100nm.
5. the preparation method of ionic liquid-epoxy resin composite material as claimed in claim 4, it is characterized in that: the consumption of described palygorskite is 1 ~ 9% of Resins, epoxy quality.
6. such as the preparation method of arbitrary ionic liquid-epoxy resin composite material as described in the claim 1 ~ 5, it is characterized in that: with Resins, epoxy heating liquefaction, after the thinner dilution, add toughner, after stirring, add palygorskite, ionic liquid, mix, Fruit storage, add solidifying agent, stir, again vacuumize processing, reverse mould solidifies 12 ~ 24h and both got in 50 ~ 70 ℃ of baking ovens.
7. the preparation method of ionic liquid epoxy resin composite material as claimed in claim 6 is characterized in that: described thinner is the mixed solution that is formed with the volume ratio of 1:2 ~ 1:4 by dimethylbenzene and propyl carbinol.
8. the preparation method of ionic liquid epoxy resin composite material as claimed in claim 6, it is characterized in that: described toughner is butylene phthalate, its add-on is 0.2 ~ 0.8% of Resins, epoxy quality.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN108864679A (en) * | 2018-07-18 | 2018-11-23 | 望江县天长光学仪器有限公司 | A kind of preparation method of wear-resisting lens |
| WO2020059434A1 (en) * | 2018-09-21 | 2020-03-26 | サンアプロ株式会社 | Epoxy resin composition |
| FR3091406A1 (en) * | 2018-12-31 | 2020-07-03 | Centre National De Recherche Scientifique (Cnrs) | Material for electrical insulation and manufacturing process |
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| US20030008125A1 (en) * | 2001-07-05 | 2003-01-09 | Curt Delanoy | Composite carbon fiber material and method of making same |
| CN102504672A (en) * | 2011-10-28 | 2012-06-20 | 西北师范大学 | Epoxy resin-based wear-resistant anticorrosive material |
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| US20030008125A1 (en) * | 2001-07-05 | 2003-01-09 | Curt Delanoy | Composite carbon fiber material and method of making same |
| CN102504672A (en) * | 2011-10-28 | 2012-06-20 | 西北师范大学 | Epoxy resin-based wear-resistant anticorrosive material |
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Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN108864679A (en) * | 2018-07-18 | 2018-11-23 | 望江县天长光学仪器有限公司 | A kind of preparation method of wear-resisting lens |
| WO2020059434A1 (en) * | 2018-09-21 | 2020-03-26 | サンアプロ株式会社 | Epoxy resin composition |
| JPWO2020059434A1 (en) * | 2018-09-21 | 2021-09-30 | サンアプロ株式会社 | Epoxy resin composition |
| JP7328240B2 (en) | 2018-09-21 | 2023-08-16 | サンアプロ株式会社 | epoxy resin composition |
| FR3091406A1 (en) * | 2018-12-31 | 2020-07-03 | Centre National De Recherche Scientifique (Cnrs) | Material for electrical insulation and manufacturing process |
| WO2020141280A1 (en) | 2018-12-31 | 2020-07-09 | Supergrid Institute | Electrical insulation material and manufacturing process |
| CN113227236A (en) * | 2018-12-31 | 2021-08-06 | 超级电力研究所有限公司 | Electrical insulation material and method of manufacture |
| CN113227236B (en) * | 2018-12-31 | 2023-06-02 | 超级电力研究所有限公司 | Electrical insulation material and method of manufacture |
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| Publication number | Publication date |
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| CN102964778B (en) | 2015-08-05 |
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