CN107840942B - Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione and preparation method thereof - Google Patents
Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione and preparation method thereof Download PDFInfo
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- CN107840942B CN107840942B CN201711184906.3A CN201711184906A CN107840942B CN 107840942 B CN107840942 B CN 107840942B CN 201711184906 A CN201711184906 A CN 201711184906A CN 107840942 B CN107840942 B CN 107840942B
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- curing agent
- ring structure
- latent curing
- type latent
- triazinetrione
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 title claims abstract description 156
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 title claims abstract description 76
- 239000003795 chemical substances by application Substances 0.000 title claims abstract description 61
- 238000002360 preparation method Methods 0.000 title claims description 21
- 239000003822 epoxy resin Substances 0.000 claims abstract description 25
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 25
- -1 glyoxaline compound Chemical class 0.000 claims abstract description 17
- 238000007259 addition reaction Methods 0.000 claims abstract 2
- 238000006243 chemical reaction Methods 0.000 claims description 28
- 229910052739 hydrogen Inorganic materials 0.000 claims description 21
- 239000001257 hydrogen Substances 0.000 claims description 21
- 239000002904 solvent Substances 0.000 claims description 13
- 150000002460 imidazoles Chemical group 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000003756 stirring Methods 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 6
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 5
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 claims description 4
- LLEASVZEQBICSN-UHFFFAOYSA-N 2-undecyl-1h-imidazole Chemical compound CCCCCCCCCCCC1=NC=CN1 LLEASVZEQBICSN-UHFFFAOYSA-N 0.000 claims description 3
- ULKLGIFJWFIQFF-UHFFFAOYSA-N 5K8XI641G3 Chemical compound CCC1=NC=C(C)N1 ULKLGIFJWFIQFF-UHFFFAOYSA-N 0.000 claims description 3
- LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 claims description 2
- XHLKOHSAWQPOFO-UHFFFAOYSA-N 5-phenyl-1h-imidazole Chemical compound N1C=NC=C1C1=CC=CC=C1 XHLKOHSAWQPOFO-UHFFFAOYSA-N 0.000 claims description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 claims description 2
- MHABMANUFPZXEB-UHFFFAOYSA-N O-demethyl-aloesaponarin I Natural products O=C1C2=CC=CC(O)=C2C(=O)C2=C1C=C(O)C(C(O)=O)=C2C MHABMANUFPZXEB-UHFFFAOYSA-N 0.000 claims description 2
- 229940113088 dimethylacetamide Drugs 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims 4
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims 2
- 150000003851 azoles Chemical class 0.000 claims 1
- 238000003860 storage Methods 0.000 abstract description 8
- 239000000203 mixture Substances 0.000 abstract description 4
- 238000010189 synthetic method Methods 0.000 abstract 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 12
- OUPZKGBUJRBPGC-UHFFFAOYSA-N 1,3,5-tris(oxiran-2-ylmethyl)-1,3,5-triazinane-2,4,6-trione Chemical compound O=C1N(CC2OC2)C(=O)N(CC2OC2)C(=O)N1CC1CO1 OUPZKGBUJRBPGC-UHFFFAOYSA-N 0.000 description 9
- 238000001228 spectrum Methods 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 3
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 238000005259 measurement Methods 0.000 description 3
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 3
- ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 2-phenyl-1h-imidazole Chemical compound C1=CNC(C=2C=CC=CC=2)=N1 ZCUJYXPAKHMBAZ-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000000284 resting effect Effects 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- OSNIIMCBVLBNGS-UHFFFAOYSA-N 1-(1,3-benzodioxol-5-yl)-2-(dimethylamino)propan-1-one Chemical compound CN(C)C(C)C(=O)C1=CC=C2OCOC2=C1 OSNIIMCBVLBNGS-UHFFFAOYSA-N 0.000 description 1
- LYWVNPSVLAFTFX-UHFFFAOYSA-N 4-methylbenzenesulfonate;morpholin-4-ium Chemical compound C1COCCN1.CC1=CC=C(S(O)(=O)=O)C=C1 LYWVNPSVLAFTFX-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 235000009508 confectionery Nutrition 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000010292 electrical insulation Methods 0.000 description 1
- 238000003912 environmental pollution Methods 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- XLSZMDLNRCVEIJ-UHFFFAOYSA-N methylimidazole Natural products CC1=CNC=N1 XLSZMDLNRCVEIJ-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000007711 solidification Methods 0.000 description 1
- 230000008023 solidification Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- 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
- C08G59/62—Alcohols or phenols
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
- C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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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)
Abstract
The invention discloses the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula is as follows:
Description
Technical field
The present invention relates to epoxy resin lalent solidifying agent and preparation method thereof technical fields, and in particular to one kind contains triazine
The imidazoles epoxy resin lalent solidifying agent of triketone ring structure.
Background technique:
In recent years, epoxy resin lalent solidifying agent is the research hotspot in domestic and international epoxy curing agent field.With mesh
Before the bi-component epoxide-resin system that generallys use compare, it is seperated with single group made of epoxy preparation as latent curing agent
System has many advantages, such as that production operation simple process, reduction environmental pollution, product quality is uniform, is convenient for industrialized production.
Imidazole curing agent can cause the polymerization of epoxy resin anionic chain, with dosage is few, curing efficiency is high, solidfied material
The features such as chemical mediator-resitant property, mechanical property and electrical insulation capability are good, has broad application prospects.However, plain imidazole
Class curing agent and epoxy resin compatibility are poor, and room temperature working life is short, to limit its application.
Summary of the invention
The technical problem to be solved by the present invention is to provide a kind of containing triazine in view of the deficiency of the prior art
The Imidazole Type Latent Curing Agent of triketone ring structure, good with epoxy resin compatibility, the single-component system storage period of composition is long,
It under mesophilic condition can fast-curing epoxy resin.
The present invention be solve the problems, such as it is set forth above used by technical solution are as follows:
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1Selected from one of including but not limited to hydrogen, methyl, ethyl, phenyl or undecyl etc., R2It is selected from
Including but not limited to one of hydrogen, methyl or phenyl etc..
It is anti-that the present invention uses glyoxaline compound and isocyanuric acid three-glycidyl ester containing active N-H key to carry out addition
It answers, obtains the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, synthetic route is as follows:
The Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione the preparation method is as follows: with isocyanuric acid three contracting
Water glyceride (TGIC) and glyoxaline compound containing active N-H key are raw material, first by the imidazoles chemical combination containing active N-H key
Object and solvent are uniformly mixed in reaction flask, and TGIC is then gradually added into reaction flask under 90-150 DEG C, stirring condition；
After TGIC is added, 4-8h is stirred to react under the conditions of 110-150 DEG C；After reaction, revolving removes solvent, obtains containing three
The Imidazole Type Latent Curing Agent of piperazine triketone ring structure.
According to the above scheme, in the preparation method, the glyoxaline compound containing active N-H key has following molecule knot
Structure:
Wherein, R1Selected from one of including but not limited to hydrogen, methyl, ethyl, phenyl or undecyl etc., R2It is selected from
Including but not limited to one of hydrogen, methyl or phenyl etc..
It is further preferred that the glyoxaline compound containing active N-H key is selected from including but not limited to imidazoles, 2- first
In base imidazoles, 2- ethyl imidazol(e), 2- phenylimidazole, 2-ethyl-4-methylimidazole, 4- phenylimidazole or 2- undecyl imidazole etc.
One kind.
According to the above scheme, in the preparation method, the glyoxaline compound containing active N-H key shrinks sweet with isocyanuric acid three
The molar ratio of grease is 2.9-3.1:1.
According to the above scheme, in the preparation method, solvent be selected from dimethylbenzene, dimethyl sulfoxide, n,N-Dimethylformamide or
One of DMAC N,N' dimethyl acetamide etc..
Compared with prior art, beneficial effects of the present invention are as follows:
The present invention is prepared for the addition product of glyoxaline compound and isocyanuric acid three-glycidyl ester, has obtained containing triazine
The Imidazole Type Latent Curing Agent of triketone ring structure, the epoxy resin single-component system of composition good with epoxy resin compatibility
Storage period is long, under mesophilic condition can fast-curing epoxy resin, overcome imidazole curing agent working life short disadvantage.
Second, the present invention is added using the glyoxaline compound containing active N-H key with isocyanuric acid three-glycidyl ester
At reaction, the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione is obtained, synthesis technology is simple, and yield is high, and raw material is easy to get,
It is suitble to industrialized production.
Detailed description of the invention
Fig. 1 is the nucleus magnetic hydrogen spectrum figure of curing agent A；
Fig. 2 is the nucleus magnetic hydrogen spectrum figure of curing agent B；
Fig. 3 is the nucleus magnetic hydrogen spectrum figure of curing agent C；
Fig. 4 is the nucleus magnetic hydrogen spectrum figure of curing agent D；
Fig. 5 is the nucleus magnetic hydrogen spectrum figure of curing agent E；
Fig. 6 is the nucleus magnetic hydrogen spectrum figure of curing agent F；
Fig. 7 is the nucleus magnetic hydrogen spectrum figure of curing agent G.
Specific embodiment
For a better understanding of the present invention, below with reference to the embodiment content that the present invention is furture elucidated, but the present invention is not
It is limited only to the following examples.
Embodiment 1
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1And R2It is hydrogen.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows:
By 20.4g imidazoles and 300mlN, dinethylformamide is uniformly mixed in reaction flask, then in 90 DEG C, stirring
Under the conditions of 29.7g isocyanuric acid three-glycidyl ester is gradually added into reaction flask；Isocyanuric acid three-glycidyl ester has been added
Bi Hou is stirred to react 4h under the conditions of 110 DEG C；After reaction, revolving removes solvent, obtains the miaow of the ring structure containing triazinetrione
Azole latent curing agent (number: A).
Embodiment 2
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For methyl and R2For hydrogen.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
24.6g2- methylimidazole and 300mlN, dinethylformamide is uniformly mixed in reaction flask, then in 120 DEG C, stirring bar
29.7g isocyanuric acid three-glycidyl ester is gradually added under part into reaction flask；After TGIC is added, under the conditions of 130 DEG C
It is stirred to react 5h；After reaction, revolving removes solvent, obtains the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione
(number: B).
Embodiment 3
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For ethyl and R2For hydrogen.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
28.8g2- ethyl imidazol(e) and 300mlN, dinethylformamide is uniformly mixed in reaction flask, then in 130 DEG C, stirring bar
29.7g isocyanuric acid three-glycidyl ester is gradually added under part into reaction flask；After TGIC is added, under the conditions of 140 DEG C
It is stirred to react 5h；After reaction, revolving removes solvent, obtains the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione
(number: C).
Embodiment 4
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For phenyl and R2For hydrogen.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
43.2g2- phenylimidazole and 400mlN, dinethylformamide is uniformly mixed in reaction flask, then in 130 DEG C, stirring bar
29.7g isocyanuric acid three-glycidyl ester is gradually added under part into reaction flask；After TGIC is added, under the conditions of 150 DEG C
It is stirred to react 6h；After reaction, revolving removes solvent, obtains the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione
(number: D).
Embodiment 5
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For ethyl and R2For methyl.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
33g2- ethyl -4-methylimidazole and 300mlN, dinethylformamide in reaction flask be uniformly mixed, then 130 DEG C, stir
29.7g isocyanuric acid three-glycidyl ester is gradually added under the conditions of mixing into reaction flask；After TGIC is added, in 140 DEG C of items
5h is stirred to react under part；After reaction, revolving removes solvent, obtains the imidazoles latent curing of the ring structure containing triazinetrione
Agent (number: E).
Embodiment 6
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For hydrogen and R2For phenyl.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
43.2g4- phenylimidazole and 350mlN, dinethylformamide is uniformly mixed in reaction flask, then in 135 DEG C, stirring bar
29.7g isocyanuric acid three-glycidyl ester is gradually added under part into reaction flask；After TGIC is added, under the conditions of 145 DEG C
It is stirred to react 7h；After reaction, revolving removes solvent, obtains the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione
(number: F).
Embodiment 7
The Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, molecular structural formula are as follows:
Wherein, R1For undecyl and R2For hydrogen.
The preparation method of the Imidazole Type Latent Curing Agent of the above-mentioned ring structure containing triazinetrione, the specific steps are as follows: will
66.6g2- undecyl imidazole and 400mlN, dinethylformamide in reaction flask be uniformly mixed, then 140 DEG C, stir
29.7g isocyanuric acid three-glycidyl ester is gradually added under the conditions of mixing into reaction flask；After TGIC is added, in 150 DEG C of items
8h is stirred to react under part；After reaction, revolving removes solvent, obtains the imidazoles latent curing of the ring structure containing triazinetrione
Agent (number: G).
Application examples
Respectively and bisphenol A-type with the Imidazole Type Latent Curing Agent A-G of the ring structure containing triazinetrione made from embodiment 1-7
Epoxy resin (E-51 epoxy resin, trade mark CYD-128, Yueyang petrochemical industry Co., Ltd, Ba Ling Huaxing) 5:100 in mass ratio mixing,
Solidification test is carried out using differential scanning calorimeter, heating rate is 10 DEG C/min.The storage period of sample is referring to GB/T7123.2-
2002 measurements, above-mentioned prepared epoxy resin solidifying system is put into constant temperature control box, maintains the temperature at 25 DEG C, measurement is solid
Change system is still able to maintain the maximum resting period of its operating characteristics.
The curing performance parameter of 1 Imidazole Type Latent Curing Agent of table and working life
Comparative example: by imidazoles, 2-methylimidazole, 2- ethyl imidazol(e), 2- phenylimidazole, 2-ethyl-4-methylimidazole, 4- benzene
Base imidazoles and 2- undecyl imidazole respectively with bisphenol A type epoxy resin (E-51 epoxy resin, trade mark CYD-128, Yueyang bar
Petrochemical industry Co., Ltd, mound Huaxing) mixing of 5:100 in mass ratio.The storage period of sample measures referring to GB/T7123.2-2002, will be upper
It states prepared epoxy resin solidifying system to be put into constant temperature control box, maintains the temperature at 25 DEG C, measurement curing system remains to protect
Hold the maximum resting period of its operating characteristics.
As shown in Table 1, the Storage period for the one-component system that the 7 kinds of imidazole curing agents with epoxy resin of comparative example form is equal
Less than 5 days；And curing agent A-G prepared by the present invention and epoxy resin composition one-component system Storage period 15 days with
On, Storage period substantially extends, and is easily uniformly mixed with epoxy resin, and under mesophilic condition can fast-curing epoxy resin.
The above is only a preferred embodiment of the present invention, it is noted that come for those of ordinary skill in the art
It says, without departing from the concept of the premise of the invention, several modifications and variations can also be made, these belong to of the invention
Protection scope.
Claims (9)
1. the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, it is characterised in that its molecular structural formula is as follows:
Wherein, R1Selected from one of hydrogen, alkyl, phenyl, R2Selected from one of hydrogen, alkyl or phenyl.
2. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure containing triazinetrione, it is characterised in that its key step is such as
Under: glyoxaline compound and isocyanuric acid three-glycidyl ester containing active N-H key carry out addition reaction, obtain and contain triazinetrione
The Imidazole Type Latent Curing Agent of ring structure.
3. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure according to claim 2 containing triazinetrione, special
Sign be first by containing active N-H key glyoxaline compound and solvent in reaction flask be uniformly mixed, then 90-150 DEG C,
Isocyanuric acid three-glycidyl ester is gradually added under stirring condition into reaction flask；Isocyanuric acid three-glycidyl ester addition finishes
Afterwards, 4-8h is stirred to react under the conditions of 110-150 DEG C；After reaction, solvent is removed, the miaow of the ring structure containing triazinetrione is obtained
Azole latent curing agent.
4. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure according to claim 2 or 3 containing triazinetrione,
It is characterized in that the glyoxaline compound containing active N-H key has following molecular structure:
Wherein, R1Selected from one of hydrogen, alkyl, phenyl, R2Selected from one of hydrogen, alkyl or phenyl.
5. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure according to claim 2 or 3 containing triazinetrione,
It is characterized in that the glyoxaline compound containing active N-H key is selected from imidazoles, 2-methylimidazole, 2- ethyl imidazol(e), 2- phenyl miaow
One of azoles, 2-ethyl-4-methylimidazole, 4- phenylimidazole or 2- undecyl imidazole.
6. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure according to claim 2 or 3 containing triazinetrione,
The molar ratio for being characterized in that the glyoxaline compound and isocyanuric acid three-glycidyl ester containing active N-H key is 2.9-3.1:
1。
7. the preparation method of the Imidazole Type Latent Curing Agent of the ring structure according to claim 3 containing triazinetrione, special
Sign is that solvent is selected from one of dimethylbenzene, dimethyl sulfoxide, N,N-dimethylformamide or DMAC N,N' dimethyl acetamide.
8. Imidazole Type Latent Curing Agent the answering in epoxy-resin systems of the ring structure described in claim 1 containing triazinetrione
With.
9. the Imidazole Type Latent Curing Agent of the ring structure described in claim 1 containing triazinetrione is in one-component epoxy resin system
Application.
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| CN112194779A (en) * | 2020-10-09 | 2021-01-08 | 江南大学 | Single-component epoxy resin composition containing latent imidazole curing accelerator and preparation method and application thereof |
| CN116426192A (en) * | 2023-03-02 | 2023-07-14 | 庞贝捷粉末涂料(上海)有限公司 | Low temperature curing powder coating compositions |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000290260A (en) * | 1999-04-01 | 2000-10-17 | Shikoku Chem Corp | New imidazole compound and epoxy resin curing agent comprising imidazole compound as active ingredient |
| CN101362819A (en) * | 2008-09-10 | 2009-02-11 | 华南理工大学 | Triazines cross-linking compounds, preparation method and application thereof |
| TW201332981A (en) * | 2011-12-30 | 2013-08-16 | Cheil Ind Inc | Cyanuric acid derivatives and resist underlayer composition including the cyanuric acid derivatives and method of forming patterns using the resist underlayer composition |
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2017
- 2017-11-23 CN CN201711184906.3A patent/CN107840942B/en not_active Expired - Fee Related
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2000290260A (en) * | 1999-04-01 | 2000-10-17 | Shikoku Chem Corp | New imidazole compound and epoxy resin curing agent comprising imidazole compound as active ingredient |
| CN101362819A (en) * | 2008-09-10 | 2009-02-11 | 华南理工大学 | Triazines cross-linking compounds, preparation method and application thereof |
| TW201332981A (en) * | 2011-12-30 | 2013-08-16 | Cheil Ind Inc | Cyanuric acid derivatives and resist underlayer composition including the cyanuric acid derivatives and method of forming patterns using the resist underlayer composition |
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