CN118930814B - Epoxy resin curing indicator compound and preparation method and composition - Google Patents
Epoxy resin curing indicator compound and preparation method and compositionInfo
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- CN118930814B CN118930814B CN202411286172.XA CN202411286172A CN118930814B CN 118930814 B CN118930814 B CN 118930814B CN 202411286172 A CN202411286172 A CN 202411286172A CN 118930814 B CN118930814 B CN 118930814B
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- epoxy resin
- resin curing
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- 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
- C08G59/4007—Curing agents not provided for by the groups C08G59/42 - C08G59/66
- C08G59/4014—Nitrogen containing compounds
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
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- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Epoxy Resins (AREA)
Abstract
本申请属于电工绝缘材料技术领域，尤其涉及一种环氧树脂固化指示化合物及制备方法和组合物；本申请提供的一种环氧树脂固化指示化合物可以随着固化反应的进行，使得固化环氧树脂的颜色逐渐从无色变成红色，再变成深红色，从而人们可以通过眼睛的视觉效应，直观观察物体的颜色，判断环氧树脂的固化程度；并且通过预先建立的固化时间和吸光率的线性关系式，还可以更为精确的判断环氧树脂的固化时间，解决了现有技术中缺乏直观判断环氧树脂的固化程度的技术问题。
The present application belongs to the technical field of electrical insulation materials, and in particular relates to an epoxy resin curing indicator compound, a preparation method, and a composition. The epoxy resin curing indicator compound provided in the present application can gradually change the color of the cured epoxy resin from colorless to red and then to dark red as the curing reaction proceeds, so that people can visually observe the color of the object and judge the curing degree of the epoxy resin through the visual effect of the eyes. In addition, through a pre-established linear relationship between curing time and absorbance, the curing time of the epoxy resin can be more accurately judged, solving the technical problem of the lack of intuitive judgment of the curing degree of the epoxy resin in the prior art.
Description
Technical Field
The application belongs to the technical field of electrical insulating materials, and particularly relates to an epoxy resin curing indicating compound, a preparation method and a composition.
Background
The epoxy resin is a polymer containing more than two epoxy groups, is a high-molecular thermosetting polymer, can be subjected to ring opening, curing and crosslinking by using various curing agents containing active hydrogen to generate a net structure due to the chemical activity of the epoxy groups, can be crosslinked and cured by using curing agents such as an alkaline curing agent, an acidic curing agent, an addition type curing agent, a catalytic curing agent, a explicit curing agent and the like, and has the advantages of high insulating property, high structural strength, good sealing property and the like, and is widely applied to the fields of high-low voltage electric appliances, motors, electronic components and the like as an insulating material of electric engineering.
The curing degree of the epoxy resin can be obtained according to the residual reaction heat of the epoxy resin and the reaction heat of the complete curing of the epoxy resin, and besides the differential scanning calorimetry, the curing degree of the epoxy resin can influence the mechanical property of the epoxy resin, so that the curing degree of the epoxy resin can be reflected according to the mechanical property by an impact test method for measuring the toughness of an epoxy resin sample, a hardness test method for measuring the hardness of the epoxy resin sample, a bending test method for measuring the bending strength and the bending modulus of the epoxy resin sample and other mechanical property test methods.
However, the testing methods such as a differential scanning calorimetry method, toughness, hardness, bending strength, bending modulus and the like all need additional instruments and equipment, the curing degree of the epoxy resin can be judged according to the testing results of the instruments and equipment, and the current lack of a visual method for judging the curing degree of the epoxy resin is visual, so that the color of an object can be visually observed through the visual effect of eyes under the condition that the epoxy resin is not damaged.
Disclosure of Invention
In view of the above, the present application provides an epoxy resin curing indicating compound, a preparation method and a composition thereof, which are used for solving the technical problem that the prior art lacks visual judgment of the curing degree of epoxy resin.
The first aspect of the application provides an epoxy resin curing indicating compound, wherein the chemical structure of the epoxy resin curing indicating compound is shown as a formula I;
formula I.
In formula I, et is selected from alkyl.
Preferably, the alkyl group is selected from any one of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl and hexyl.
The second aspect of the present application provides a method for preparing an epoxy resin curing indicating compound according to the first aspect, comprising the steps of:
Step S1, reacting 1- { [ (2-methylpropan-2-yl) oxy ] carbonyl } piperidine-4-carboxylic acid, 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethan-1-ol and at room temperature to give piperidine-4-carboxylic acid 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethyl ester;
Step S2, reacting piperidine-4-carboxylic acid 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethyl ester, 2- (4- { [ dimethyl (2-methylpropan-2-yl) sily l ] oxy } phenyl) -2-glycolic acid at room temperature to obtain 2- (4- { [ dimethyl (2-methylpropan-2-yl) silyl ] oxy } phenyl) -1- [4- ({ [2- (ethyl {4- [ (4-nitrophenyl) ethanyl ] phenyl } amino) ethyl ] dioxy } thio) hexahydropyridin-1-yl ] -2-hydroxyethyl-1-one;
Step S3, reacting 2- (4- { [ dimethyl (2-methylpropan-2-yl) silyl ] oxy } phenyl) -1- [4- ({ [2- (ethyl {4- [ (4-nitrophenyl) ethylenyl ] phenyl } amino) ethyl ] dioxy } thio) hexahydropyridin-1-yl ] -2-hydroxyethyl-1-one and p-nitrobenzoate at room temperature to obtain the epoxy resin curing indication compound shown in the formula I.
Preferably, in the step S1, the reaction process comprises the step of reacting for 6-18 hours in a mixed reaction system of 4-dimethylaminopyridine, dichloromethane and 1-ethyl- (3-dimethylaminopropyl) carbodiimide.
Preferably, in the step S2, the reaction process comprises the step of reacting for 4-8 hours in a mixed reaction system of diisopropylethylamine, benzotriazole-N, N, N ', N' -tetramethylurea hexafluorophosphate and N, N-dimethylformamide.
Preferably, in the step S3, the reaction process comprises the step of reacting for 6-18 hours in a mixed reaction system of 2, 6-lutidine and dichloromethane.
The application provides an epoxy resin curing indication composition, which comprises colorless transparent epoxy resin, a colorless transparent epoxy resin curing agent and an epoxy resin curing indication compound.
Preferably, in the epoxy resin curing indication composition, the colorless transparent epoxy resin is selected from bisphenol a type epoxy resin, and the colorless transparent epoxy resin curing agent is selected from polyoxypropylene triamine.
Preferably, in the epoxy resin curing indication composition, the volume ratio of bisphenol A type epoxy resin to polyoxypropylene triamine is 100:30-60.
Preferably, in the epoxy resin curing indication composition, the doping amount of the compound shown in the formula I is 0.005% -0.015% (V/V).
Preferably, the epoxy resin curing indication composition further comprises butanediol diglycidyl ether, C13-C15-glycidyl ether and benzyl alcohol.
In a fourth aspect, the present application provides a use of an epoxy cure indicating composition for determining epoxy cure.
Preferably, the application specifically comprises the steps of:
s1, curing an epoxy resin curing indication composition, and recording the absorbance of the epoxy resin at different curing times;
s2, establishing a linear relation between the absorbance of the epoxy resin and the curing time according to the absorbance of the epoxy resin at different curing times;
And S3, substituting the absorbance of the epoxy resin curing indication composition to be tested, which has the same formula as the epoxy resin curing indication composition, into a linear relation between the absorbance of the epoxy resin and the curing time to obtain the curing time of the epoxy resin curing indication composition to be tested.
Preferably, in step S1, the absorbance of the epoxy resin recorded with different curing times is specifically:
The absorbance of the epoxy resin was recorded with a uv-vis-nir spectrometer for curing times of 10min, 20min, 30min, 40min, 60 min.
Preferably, in step S2, the linear relationship between the absorbance of the epoxy resin and the curing time is y=0.0275 x-0.165, r 2 =0.9494, y is absorbance, and x is curing time.
In summary, the application provides an epoxy resin curing indicating compound, a preparation method and a composition thereof, wherein the epoxy resin curing indicating compound can be introduced into an epoxy resin cross-linked network as a chromophore after a three-dimensional cross-linked network of a cured epoxy resin generated by colorless transparent epoxy resin such as bisphenol A epoxy resin and colorless transparent epoxy resin curing agents such as polyoxypropylene triamine, and the network structure of the cured epoxy resin contains more and more chromophores along with the progress of the epoxy resin curing reaction, so that the color of the epoxy resin is gradually changed from colorless to light red, red and dark red along with the progress of the epoxy resin curing reaction, and the color of the epoxy resin is changed, so that people can directly observe the epoxy resin through eyes without damaging the epoxy resin, and judge that the curing degree of the epoxy resin is larger when people observe the color of the epoxy resin to be more red, thereby solving the technical problem that the prior art lacks visual judgment of the curing degree of the epoxy resin.
Drawings
In order to more clearly illustrate the embodiments of the present application or the technical solutions in the prior art, the drawings that are needed in the description of the embodiments or the prior art will be briefly described, and it is obvious that the drawings in the description below are some embodiments of the present application, and other drawings can be obtained according to the drawings without inventive effort for a person skilled in the art.
FIG. 1 is a schematic flow chart of a preparation method of the epoxy resin curing indicator compound in the embodiment 1 of the application;
FIG. 2 is a nuclear magnetic resonance spectrum of an epoxy resin curing indicating compound according to example 1 of the present application;
FIG. 3 is a graph showing absorbance of epoxy resins with different curing times (10 min, 20min, 30min, 40min, 60 min) as described in example 3 of the present application;
FIG. 4 is a graph showing the results of fitting the absorbance of epoxy resins at various curing times (10 min, 20min, 30min, 40min, 60 min) as described in example 4 of the present application.
Detailed Description
The application provides an epoxy resin curing indicating compound, a preparation method and a composition thereof, which are used for solving the technical problem that the prior art lacks visual judgment of the curing degree of epoxy resin.
The following description of the embodiments of the present application will be made apparent and fully in view of the accompanying drawings, in which some, but not all embodiments of the application are shown. All other embodiments, which can be made by those skilled in the art based on the embodiments of the application without making any inventive effort, are intended to be within the scope of the application.
In view of the defect that the existing method for intuitively judging the curing degree of epoxy resin is lack, the application provides an epoxy resin curing indication compound, the structure of which is shown as a formula I, the epoxy resin is subjected to curing reaction under the action of a curing agent, the generated three-dimensional crosslinked network of the cured epoxy resin is provided, the epoxy resin curing indication compound can be introduced into the epoxy resin crosslinked network as a chromophore, the chromophore can absorb light with a certain wavelength in light and does not absorb light with another wavelength, so that the cured epoxy resin containing the chromophore shows the corresponding color of the absorption wavelength, the more and more chromophores are introduced into the cured epoxy resin along with the curing reaction of the epoxy resin, the darker and darker the color of the cured epoxy resin is obtained, the lighter the color is, the lower the curing degree of the epoxy resin is indicated, the darker the color is indicated, the greater the curing degree of the epoxy resin is indicated, and meanwhile, the problem that an extra instrument is required for performance test such as a poor scanning calorimeter, toughness, hardness, bending strength and bending modulus is required, and the like, and the problem that the epoxy resin is required to be damaged is overcome, so that the defect of intuitively judging the curing degree of the epoxy resin is overcome.
Preferably, the application also provides an epoxy resin curing indication composition, which is obtained by mixing an epoxy resin curing indication compound, colorless transparent epoxy resin and colorless transparent epoxy resin curing agent.
Preferably, in the epoxy resin curing indication composition provided by the application, the colorless transparent epoxy resin is selected from bisphenol A epoxy resin, the colorless transparent epoxy resin curing agent is selected from polyoxypropylene triamine, and the compound shown in the formula I is combined with a group (amine or alcohol) generated in a crosslinked network after the bisphenol A epoxy resin is cured to generate a wavelength color capable of absorbing about 650nm and a wavelength corresponding to red light, so that the cured epoxy resin gradually changes from colorless to light red, gradually changes from light red to red and then changes into dark red.
Preferably, in the epoxy resin curing indication composition provided by the application, the doping amount of the epoxy resin curing indication compound is 0.005% -0.015% (V/V). Namely, 0.005 to 0.015ml of the epoxy resin curing indicating compound is mixed with 100ml of the epoxy resin curing indicating composition.
Preferably, the volume ratio of the colorless transparent epoxy resin to the colorless transparent epoxy resin curing agent in the epoxy resin curing indication composition is 100:30-60, and dilution solvent components such as butanediol diglycidyl ether, C13-C15-glycidyl ether, benzyl alcohol and the like are also added.
The application also establishes a quantification method of the epoxy resin curing degree by utilizing the relation between the curing degree of the epoxy resin curing indication composition and the color change, and determines the curing time of the epoxy resin according to the color of the epoxy resin by considering that the curing time has a great influence on the curing of the epoxy resin.
The following will specifically explain an epoxy resin curing indicating composition and a judging method according to the present application by referring to examples and experimental examples.
Example 1
The embodiment 1 of the application provides a preparation method of an epoxy resin curing indicating compound, wherein the flow of the preparation method is shown in figure 1, and the preparation method comprises the following steps:
A mixture of 1.15g of 1- { [ (2-methylpropan-2-yl) oxy ] carbonyl } hexahydropyridine-4-carboxylic acid (5.0 mmol), 61.3mg of DMAP (0.50 mmol), 20ml of CH 2Cl2, 1.15g of EDC (6.0 mmol) was allowed to stand at 0℃for 10 minutes, and then 1.74 g g of 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethan-1-ol (5.5 mmol) was added to the above solution, and after stirring and mixing at room temperature for 12 hours, 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethyl hexahydropyridine-4-carboxylic acid was obtained;
1.824g of 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethylenyl ] phenyl } amino) ethyl hexahydropyridine-4-carboxylate (4.29 mmol) and 1.104g of 2- (4- { [ dimethyl (2-methylpropan-2-yl) sily l ] oxy } phenyl) -2-glycolic acid (3.89 mmol) were dissolved in 50mL of DMF with stirring, and 2.13 mL of DIEA (1.06 mmol) and 0.597g of HBTU (3.89 mmol) were added and reacted at room temperature for 6h to give 2- (4- { [ dimethyl (2-methylpropan-2-yl) sily ] oxy } phenyl) -1- [4- ({ [2- (ethyl {4- [ (4-nitrophenyl) ethylenyl ] phenyl } amino) ethyl ] dioxo } thio) hexahydropyridine-1-yl ] -2-hydroxyethyl-1-one;
After 0.100g of 2- (4- { [ dimethyl (2-methylpropan-2-yl) silyl ] oxy } phenyl) -1- [4- ({ [2- (ethyl {4- [ (4-nitrophenyl) ethan-enyl ] phenyl } amino) ethyl ] dioxy } thio) hexahydropyridin-1-yl ] -2-hydroxyethyl-1-one (0.1451 mmol) was added to 5ml of H 2Cl2, 100. Mu.L of 2, 6-dimethylpyridine (0.87 mmol), and 0.110g of p-nitrobenzoate (0.58 mmol) and reacted for 12 hours, an epoxy resin cure indicating compound was obtained, the nuclear magnetic resonance hydrogen spectrum of which was shown in FIG. 2.
Example 2
The embodiment 2 of the application provides a preparation method of an epoxy resin curing indication composition, which comprises the following steps:
80ml of bisphenol A type epoxy resin, 15ml of butanediol diglycidyl ether, 5ml of C13-C15-glycidyl ether, 2ml of benzyl alcohol, 45ml of polyoxypropylene-glycol triamine, and 0.01ml of the epoxy resin curing indicating compound provided in example 1 were mixed to obtain an epoxy resin curing indicating composition of which formulation was initially colorless.
Example 3
Embodiment 3 of the application provides a curing Performance test method of an epoxy resin curing indicating composition
Method the epoxy resin curing indication composition is put into a sample furnace of an ultraviolet-visible light-near infrared spectrometer, is cured at a fixed temperature of 80 ℃, and the absorption spectrum of the epoxy resin curing indication composition is recorded at 10min, 20min, 30min, 40min and 60min, the absorption spectrum result is shown in figure 3, and the curing time and the absorbance are shown in table 1.
TABLE 1 absorbance (%) of epoxy resin cured products at 650nm wavelength
As can be seen from FIG. 3, the absorption peaks of the absorption spectrum are red shifted within 10-30 min, the absorption peaks of the epoxy resin are about 650nm within 30min, 40min and 60min, the epoxy resin is red within 30 min-60 min, the absorption peak of the epoxy resin after curing is higher, the absorption is stronger for the wavelength of about 650nm, the red is darker, as can be seen from Table 1, the absorbance at 650nm is gradually increased along with the curing time of the epoxy resin curing indication composition, the red gradually changes to dark color, and the combination of the compound shown in the formula I and the groups (amine or alcohol) generated in the crosslinking network after curing the bisphenol A epoxy resin in the epoxy resin curing indication composition provided by the application generates the wavelength color capable of absorbing about 650nm, and the wavelength corresponds to the red light, so that the cured epoxy resin gradually changes from colorless to pale red, pale red gradually changes to red, and then changes to dark red.
In Table 1, absorbance was calculated by formula II;
A formula II;
In formula II, y is absorbance.
I 0 is the initial intensity (650 nm) of the light emitted by the light source.
I is the current spectrometer monitored intensity (650 nm).
Example 4
Example 4 of the present application provides the use of an epoxy cure indicating composition.
The application procedure was first fitted to the cure time and absorbance in table 1, and the results are shown in fig. 4, with a linear relationship of y=0.0275 x-0.165 and r 2 = 0.9494.
When an epoxy resin curing indication composition of the same formulation as in example 2 is cured for a certain period of time in a constant temperature oven at 80 ℃, the epoxy resin curing indication composition can be put into an ultraviolet-visible light-near infrared spectrometer to measure the absorbance at that time, and then the approximate curing time of the epoxy resin curing indication composition is judged according to y=0.0275x-0.165, and the curing time of the epoxy resin can be accurately judged according to the preset linear relation between the curing time and the absorbance.
The embodiments are only used to illustrate the technical scheme of the present application, but not to limit the technical scheme, and although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those skilled in the art that the technical scheme described in the foregoing embodiments may be modified or some or all technical features may be equivalently replaced, and the modification or replacement does not deviate the essence of the corresponding technical scheme from the scope of the technical scheme of the embodiments of the present application.
Claims (10)
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Citations (1)
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| WO2012123403A1 (en) * | 2011-03-11 | 2012-09-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | Epoxy resin system with visual monitoring of the hardening state |
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| JP4681542B2 (en) * | 2004-03-31 | 2011-05-11 | ニチバン株式会社 | Photo-radical curable resin composition containing epoxy resin |
| EP2295487A1 (en) * | 2009-09-11 | 2011-03-16 | Elantas GMBH | Epoxy resin curing indicator composition |
| EP2562210A1 (en) * | 2011-08-24 | 2013-02-27 | Henkel Italia S.p.A. | Indicator for cure of two-component- epoxy adhesives |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| WO2012123403A1 (en) * | 2011-03-11 | 2012-09-20 | Fraunhofer-Gesellschaft zur Förderung der angewandten Forschung e. V. | Epoxy resin system with visual monitoring of the hardening state |
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