CN105254618B - A kind of 2-methylimidazole class curing agent and preparation method thereof - Google Patents
A kind of 2-methylimidazole class curing agent and preparation method thereof Download PDFInfo
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- CN105254618B CN105254618B CN201510824506.9A CN201510824506A CN105254618B CN 105254618 B CN105254618 B CN 105254618B CN 201510824506 A CN201510824506 A CN 201510824506A CN 105254618 B CN105254618 B CN 105254618B
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- methylimidazole
- curing agent
- sulfuric acid
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- methylcoumarin
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- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical class CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 title claims abstract description 27
- 238000002360 preparation method Methods 0.000 title claims abstract description 15
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 18
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 23
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 claims description 21
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 17
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 15
- 238000001035 drying Methods 0.000 claims description 13
- 238000005406 washing Methods 0.000 claims description 13
- DLHXRDUXNVEIEY-UHFFFAOYSA-N 7-Methylcoumarin Chemical compound C1=CC(=O)OC2=CC(C)=CC=C21 DLHXRDUXNVEIEY-UHFFFAOYSA-N 0.000 claims description 12
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 12
- PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 claims description 12
- 239000007864 aqueous solution Substances 0.000 claims description 10
- 239000003153 chemical reaction reagent Substances 0.000 claims description 10
- 238000002156 mixing Methods 0.000 claims description 10
- PIRJLYFMCACMRZ-UHFFFAOYSA-N 7-(bromomethyl)chromen-2-one Chemical compound C1=CC(=O)OC2=CC(CBr)=CC=C21 PIRJLYFMCACMRZ-UHFFFAOYSA-N 0.000 claims description 9
- 238000001704 evaporation Methods 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 239000003960 organic solvent Substances 0.000 claims description 8
- 238000001816 cooling Methods 0.000 claims description 7
- 239000005457 ice water Substances 0.000 claims description 7
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 claims description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 6
- 239000004342 Benzoyl peroxide Substances 0.000 claims description 6
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 claims description 6
- 235000019400 benzoyl peroxide Nutrition 0.000 claims description 6
- 239000013078 crystal Substances 0.000 claims description 6
- 239000001630 malic acid Substances 0.000 claims description 6
- 235000011090 malic acid Nutrition 0.000 claims description 6
- 238000001953 recrystallisation Methods 0.000 claims description 6
- 229910000104 sodium hydride Inorganic materials 0.000 claims description 6
- 239000002904 solvent Substances 0.000 claims description 6
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 5
- 238000010438 heat treatment Methods 0.000 claims description 5
- 238000000034 method Methods 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 238000010992 reflux Methods 0.000 claims description 5
- 238000003756 stirring Methods 0.000 claims description 5
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical group [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 claims description 4
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 claims description 4
- 238000000605 extraction Methods 0.000 claims description 4
- 239000012074 organic phase Substances 0.000 claims description 4
- 239000012312 sodium hydride Substances 0.000 claims description 4
- 229960000583 acetic acid Drugs 0.000 claims description 3
- 239000012362 glacial acetic acid Substances 0.000 claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 2
- 229920006395 saturated elastomer Polymers 0.000 claims 1
- 239000011780 sodium chloride Substances 0.000 claims 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- PQMOXTJVIYEOQL-UHFFFAOYSA-N Cumarin Natural products CC(C)=CCC1=C(O)C(C(=O)C(C)CC)=C(O)C2=C1OC(=O)C=C2CCC PQMOXTJVIYEOQL-UHFFFAOYSA-N 0.000 abstract 1
- FSOGIJPGPZWNGO-UHFFFAOYSA-N Meomammein Natural products CCC(C)C(=O)C1=C(O)C(CC=C(C)C)=C(O)C2=C1OC(=O)C=C2CCC FSOGIJPGPZWNGO-UHFFFAOYSA-N 0.000 abstract 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 1
- 229910052794 bromium Inorganic materials 0.000 abstract 1
- ZYGHJZDHTFUPRJ-UHFFFAOYSA-N coumarin Chemical compound C1=CC=C2OC(=O)C=CC2=C1 ZYGHJZDHTFUPRJ-UHFFFAOYSA-N 0.000 abstract 1
- 230000002194 synthesizing effect Effects 0.000 abstract 1
- 239000003822 epoxy resin Substances 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
- 230000008018 melting Effects 0.000 description 3
- 229920000647 polyepoxide Polymers 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000008020 evaporation Effects 0.000 description 2
- 150000002460 imidazoles Chemical class 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- MWSKJDNQKGCKPA-UHFFFAOYSA-N 6-methyl-3a,4,5,7a-tetrahydro-2-benzofuran-1,3-dione Chemical group C1CC(C)=CC2C(=O)OC(=O)C12 MWSKJDNQKGCKPA-UHFFFAOYSA-N 0.000 description 1
- 241001274216 Naso Species 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000002330 electrospray ionisation mass spectrometry Methods 0.000 description 1
- 229940079865 intestinal antiinfectives imidazole derivative Drugs 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000012044 organic layer Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
- C07D405/02—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings
- C07D405/06—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/40—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the curing agents used
- C08G59/50—Amines
- C08G59/5046—Amines heterocyclic
- C08G59/5053—Amines heterocyclic containing only nitrogen as a heteroatom
- C08G59/5073—Amines heterocyclic containing only nitrogen as a heteroatom having two nitrogen atoms in the ring
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Epoxy Resins (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The invention discloses a kind of 2-methylimidazole class curing agent, i.e. 1- (coumarin-7-methylene)-2-methylimidazoles.The invention also discloses the preparation methods of aforementioned 2-methylimidazole class curing agent.It is the cumarin that first synthesizing methyl replaces, then is replaced through NBS bromine, is finally condensed with 2-methylimidazole.Compared with prior art, product of the present invention curing performance is better than existing imidazole curing agent；Meanwhile preparation method simple possible of the present invention, it is easy to spread.
Description
Technical Field
The invention belongs to the field of chemical synthesis, and particularly relates to a 2-methylimidazole curing agent and a preparation method thereof.
Background
Epoxy resin is widely used in the fields of adhesives, composite materials, coatings and the like. Imidazole and derivatives thereof are important epoxy resin curing agents and have excellent properties. However, the existing imidazole curing agent can not be stored for a long time as a single-component system due to higher curing activity. In order to overcome the defects, the simple imidazole compounds need to be modified to synthesize novel imidazole derivatives.
Disclosure of Invention
The invention aims to provide a 2-methylimidazole curing agent to solve the problem of short storage time in the prior art.
The technical problem to be solved by the invention is to provide the preparation method of the 2-methylimidazole curing agent.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows:
a2-methyl imidazole curing agent, namely 1- (coumarin-7-methylene) -2-methyl imidazole, has the following structural formula:
the preparation method of the 2-methylimidazole curing agent comprises the following steps:
(1) mixing m-cresol and malic acid, dropwise adding concentrated sulfuric acid in an ice water bath, stirring at room temperature for 0.1-1 h after dropwise adding is finished, and then heating to 100-150 ℃ for reacting for 1-5 h;
(2) cooling the mixed system obtained in the step (1), pouring the cooled mixed system into an ice-water mixture, extracting the mixed system by using an organic solvent, taking an organic phase, washing, drying, evaporating to dryness and recrystallizing to obtain a white acicular crystal, namely 7-methylcoumarin;
(3) sequentially adding the 7-methylcoumarin, the N-bromosuccinimide and the benzoyl peroxide obtained in the step (2) into benzene, uniformly mixing, refluxing for 4-9 h, evaporating the solvent, washing with water and recrystallizing to obtain a white needle-like crystal, namely the 7-bromomethylcoumarin;
(4) mixing 2-methylimidazole, sodium hydride and N, N-dimethylformamide, adding the 7-bromomethylcoumarin obtained in the step (3), reacting for 1-3 h at 50-90 ℃, cooling, pouring the obtained mixed system into water, extracting by using an organic solvent, taking an organic phase, washing, drying and recrystallizing to obtain the compound.
In the step (1), the mol ratio of m-cresol to malic acid is 1: 1 to 2.
In the step (1), the concentrated sulfuric acid is a sulfuric acid aqueous solution with the mass fraction of 98%; wherein in the sulfuric acid aqueous solution, the molar ratio of sulfuric acid to m-cresol is 1-2: 1.
wherein, the preferable scheme of the step (1) is as follows: mixing m-cresol and malic acid in a ratio of 1: 1, dripping 98 percent of sulfuric acid aqueous solution (the molar ratio of sulfuric acid to m-cresol in the sulfuric acid aqueous solution is 1.1: 1) in an ice water bath, stirring for 0.5h at room temperature after the addition is finished, and heating to 120 ℃ for reaction for 3h until no gas escapes.
In the step (2), the organic solvent used for extraction is ethyl acetate, and the reagent used for recrystallization is ethanol aqueous solution with 95% volume fraction.
In the step (2), the drying method is room temperature anhydrous NaSO4And (4) drying for 18-24 h, preferably 18 h.
In the step (2), the evaporation temperature is 80-85 ℃.
In the step (3), the molar ratio of the 7-methylcoumarin to the N-bromosuccinimide is 1-3: 1.
in the step (3), the mass ratio of the benzoyl peroxide to the 7-methylcoumarin is 0.01-0.03: 1.
in the step (3), the reflux temperature is 80-85 ℃, and the evaporation temperature is 80-85 ℃.
In the step (3), the reagent used for recrystallization is glacial acetic acid.
Wherein, the preferable scheme of the step (3) is as follows: mixing the 7-methylcoumarin, NBS and benzoyl peroxide obtained in the step (2) in a ratio of 1: 1: 0.01 weight ratio, sequentially adding dried benzene (solid-to-liquid ratio of 7-methylcoumarin to benzene is 1 g: 20ml), mixing, refluxing at 80 deg.C for 6 hr, evaporating solvent at 80 deg.C, and washing with hot water.
In the step (4), the molar ratio of the 2-methylimidazole to the 7-bromomethylcoumarin is 1-3: 1.
in the step (4), the molar ratio of sodium hydride to 2-methylimidazole is 3-5: 1.
in the step (4), the mass ratio of N, N-dimethylformamide to 2-methylimidazole is 50-100: 1.
in the step (4), the organic solvent used for extraction is ethyl acetate, the reagent used for washing is a saturated sodium chloride aqueous solution, the reagent used for drying is anhydrous magnesium sulfate, and the reagent used for recrystallization is methanol.
Wherein, the preferable scheme of the step (4) is as follows: 2-methylimidazole (0.19g, 2.32mmol), NaH (0.18g, 7.5mmol), and DMF10ml, stirring at room temperature, adding 7-bromomethylcoumarin (0.5g, 2.10mol), heating to 70 ℃, reacting for 2h, cooling, pouring into water, extracting with 50ml of ethyl acetate, washing with saturated sodium chloride solution, drying over anhydrous magnesium sulfate, spin-drying, and recrystallizing with methanol.
The reaction formula of the preparation method is as follows:
has the advantages that:
compared with the prior art, the curing performance of the product of the invention is superior to that of the prior imidazole curing agent; meanwhile, the preparation method is simple and feasible and is easy to popularize.
Detailed Description
The invention will be better understood from the following examples. However, those skilled in the art will readily appreciate that the description of the embodiments is only for illustrating the present invention and should not be taken as limiting the invention as detailed in the claims.
Example 1: preparation of 7-methylcoumarin
M-cresol (20ml, 0.19mol) and malic acid (25.4g, 0.19mol) are mixed, concentrated sulfuric acid (20.9g) with the mass fraction of 98% is dripped in an ice water bath, the mixture is stirred for 0.5h at room temperature after the addition, and then the mixture is heated to 120 ℃ to react for 3h until no gas escapes. Cooling, pouring into ice-water mixture, extracting with 250ml ethyl acetate for several times, combining organic layers, washing with water, and anhydrous NaSO at normal temperature4Drying for 18h, evaporating to remove the solvent at 80 ℃, and recrystallizing with 95% ethanol to obtain white needle-like crystals (12.5g, yield 43%), melting point 125-128 ℃.
Example 2: preparation of 7-bromomethylcoumarin
After mixing 7-methylcoumarin 1b (1g, 6.25mmol), NBS (1g, 5.62mmol), benzoyl peroxide (0.01g) and 20ml of dried benzene, refluxing at 80 ℃ for 6h, evaporating the solvent at 80 ℃, washing with hot water, and recrystallizing with glacial acetic acid to obtain white needle-like crystals (0.6g, yield 40%) with a melting point of 178-180 ℃.
Example 3: preparation of 2-methylimidazole curing agent
2-methylimidazole (0.19g, 2.32mmol), NaH (0.18g, 7.5mmol) and DMF10ml, stirring at room temperature, adding 7-bromomethylcoumarin (0.5g, 2.10mol), heating to 70 ℃, reacting for 2h, cooling, pouring into water, extracting with 50ml of ethyl acetate, washing with saturated sodium chloride solution, drying with anhydrous magnesium sulfate, spin-drying, and recrystallizing with methanol to obtain a light yellow solid (0.13g, yield 26%) and melting point 198-205 ℃. IR (KBr) vcm-1: 3434, 1638, 1593, 1442, 1301, 744, ESI-MS: 263[ M + Na ] +, 1 HNMR: 2.45(3H, S, -CH3), 2.90(2H, S, -CH2), 6.11 to 6.14(1H, d, -CH ═ C), 6.47 to 6.49(1H, d, ArH), 7.01 to 7.05(2H, d, ArH), 7.23 to 7.30(3H, m, -CH ═ C), 7.73(1H, S, -CH ═ N), 13.45(1H, S, -NH).
Example 4: test for curing Properties
The J-1010 electronic component pouring sealant is a bi-component, the component A is epoxy resin, the component B is a curing agent (the main component is methyl tetrahydrophthalic anhydride), and a curing accelerator in the curing agent is 2-methylimidazole. The modified 2-methylimidazole is used as a curing accelerator, other conditions are unchanged, and the performances of cured products in different curing accelerators are compared. Curing agent B component (table 1) was formulated with different accelerators, three B components in table 2 were mixed with the same a component at 30: 100 (weight) are mixed and cured according to the same process to obtain three corresponding cured products, and the properties of the three cured products are shown in a table 2.
TABLE 1 charging and Properties of the different B Components
TABLE 2 Properties of the cured products
The results show that Y2 and Y3 are superior to Y1 in heat distortion temperature, shrinkage and breakdown voltage as shown in Table 2; it is known from Y2 and Y3 that the use of a polyol solvent lowers the heat distortion temperature of the cured product and slightly increases the dielectric loss tangent; the performance of Y3 is better than that of Y1 and Y2. The result shows that the curing performance of the modified 2-methylimidazole is superior to that of the 2-methylimidazole.
Claims (7)
1. The preparation method of the 2-methylimidazole curing agent is characterized by comprising the following steps:
(1) mixing m-cresol and malic acid, dropwise adding concentrated sulfuric acid in an ice water bath, stirring at room temperature for 0.1-1 h after dropwise adding is finished, and then heating to 100-150 ℃ for reacting for 1-5 h;
(2) cooling the mixed system obtained in the step (1), pouring the cooled mixed system into an ice-water mixture, extracting the mixed system by using an organic solvent, taking an organic phase, washing, drying, evaporating to dryness and recrystallizing to obtain a white acicular crystal, namely 7-methylcoumarin;
(3) sequentially adding the 7-methylcoumarin, the N-bromosuccinimide and the benzoyl peroxide obtained in the step (2) into benzene, uniformly mixing, refluxing for 4-9 h, evaporating the solvent, washing with water and recrystallizing to obtain a white needle-like crystal, namely the 7-bromomethylcoumarin;
(4) mixing 2-methylimidazole, sodium hydride and N, N-dimethylformamide, adding 7-bromomethylcoumarin obtained in the step (3), reacting at 50-90 ℃ for 1-3 h, cooling, pouring the obtained mixed system into water, extracting by using an organic solvent, taking an organic phase, washing, drying and recrystallizing to obtain the compound;
wherein, the structural formula of the 2-methylimidazole curing agent is as follows:
wherein,
in the step (1), the mol ratio of m-cresol to malic acid is 1: 1-2;
in the step (4), the molar ratio of the 2-methylimidazole to the 7-bromomethylcoumarin is 1-3: 1; the molar ratio of sodium hydride to 2-methylimidazole is 3-5: 1; n, N-dimethylformamide and 2-methylimidazole, wherein the mass ratio of the dimethylformamide to the 2-methylimidazole is 50-100: 1.
2. the preparation method according to claim 1, wherein in the step (1), the concentrated sulfuric acid is a 98% sulfuric acid aqueous solution; wherein in the sulfuric acid aqueous solution, the molar ratio of sulfuric acid to m-cresol is 1-2: 1.
3. the method according to claim 1, wherein the organic solvent used for extraction in step (2) is ethyl acetate.
4. The method according to claim 1, wherein the reagent used for recrystallization in step (2) is a 95% volume fraction ethanol aqueous solution.
5. The preparation method according to claim 1, wherein in the step (3), the molar ratio of the 7-methylcoumarin to the N-bromosuccinimide is 1-3: 1; the mass ratio of the benzoyl peroxide to the 7-methylcoumarin is 0.01-0.03: 1.
6. the method according to claim 1, wherein in the step (3), the reagent used for recrystallization is glacial acetic acid.
7. The process according to claim 1, wherein in the step (4), the organic solvent used for the extraction is ethyl acetate, the washing reagent is a saturated aqueous solution of sodium chloride, the drying reagent is anhydrous magnesium sulfate, and the recrystallization reagent is methanol.
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| CN201510824506.9A CN105254618B (en) | 2015-11-24 | 2015-11-24 | A kind of 2-methylimidazole class curing agent and preparation method thereof |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1774424A (en) * | 2003-04-16 | 2006-05-17 | 亨斯迈先进材料（瑞士）有限公司 | 1-imidazolylmethyl-substituted-2-naphtols and their use as accelerators for low-temperature curing |
| CN102341430A (en) * | 2009-03-11 | 2012-02-01 | 日本曹达株式会社 | Epoxy resin composition, curing agent, and curing accelerator |
| CN102574984A (en) * | 2009-10-09 | 2012-07-11 | 汉高股份有限及两合公司 | A latent curing agent and epoxy compositions containing the same |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2015071753A (en) * | 2013-09-06 | 2015-04-16 | 株式会社Adeka | Curing agent and curable resin composition |
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1774424A (en) * | 2003-04-16 | 2006-05-17 | 亨斯迈先进材料（瑞士）有限公司 | 1-imidazolylmethyl-substituted-2-naphtols and their use as accelerators for low-temperature curing |
| CN102341430A (en) * | 2009-03-11 | 2012-02-01 | 日本曹达株式会社 | Epoxy resin composition, curing agent, and curing accelerator |
| CN102574984A (en) * | 2009-10-09 | 2012-07-11 | 汉高股份有限及两合公司 | A latent curing agent and epoxy compositions containing the same |
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| Title |
|---|
| Design, Synthesis, and 3D QSAR of Novel Potent and Selective Aromatase Inhibitors;Francesco Leonetti等;《J. Med. Chem.》;20041207;第47卷;第6792-6803页 * |
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