CN118930814A - Epoxy resin curing indicator compound and preparation method and composition - Google Patents
Epoxy resin curing indicator compound and preparation method and composition Download PDFInfo
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- CN118930814A CN118930814A CN202411286172.XA CN202411286172A CN118930814A CN 118930814 A CN118930814 A CN 118930814A CN 202411286172 A CN202411286172 A CN 202411286172A CN 118930814 A CN118930814 A CN 118930814A
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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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Abstract
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 thereof; according to the epoxy resin curing indicating compound provided by the application, along with the progress of a curing reaction, the color of the cured epoxy resin is gradually changed from colorless to red and then changed into dark red, so that people can intuitively observe the color of an object through the visual effect of eyes to judge the curing degree of the epoxy resin; and the curing time of the epoxy resin can be accurately judged through a pre-established linear relation between the curing time and the absorbance, so that the technical problem that the curing degree of the epoxy resin is not intuitively judged in the prior art is solved.
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
Epoxy resin is a generic term for a class of polymers containing more than two epoxy groups, and is a high molecular thermosetting polymer; due to the chemical activity of the epoxy group, a plurality of curing agents containing active hydrogen can be used for ring opening, curing and crosslinking to generate a net structure; curing agents such as alkaline curing agents, acidic curing agents, addition type curing agents, catalytic curing agents and apparent curing agents can crosslink and cure the epoxy resin; the cross-linked and solidified epoxy resin 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 electrical appliances, motors, electronic components and the like as an electrical engineering insulating material.
Curing of epoxy resin can significantly affect the performance of epoxy resin, so that researchers adopt various methods to judge the curing degree of epoxy resin; the differential scanning calorimetry can be used for researching the curing degree of the epoxy resin, and the curing reaction of the epoxy resin is exothermic, so that 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; in addition to the differential scanning calorimetry, since the degree of curing of the epoxy resin affects the mechanical properties of the epoxy resin, the degree of curing of the epoxy resin can also be reflected in terms of mechanical properties by an impact test method for measuring toughness of the epoxy resin specimen, by a hardness test method for measuring hardness of the epoxy resin specimen, by a mechanical property test method for measuring flexural strength and flexural modulus of the epoxy resin specimen, and the like.
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 step S1, the reaction includes: and (3) reacting for 6-18 h in a mixed reaction system of 4-dimethylaminopyridine, dichloromethane and 1-ethyl- (3-dimethylaminopropyl) carbodiimide.
Preferably, in step S2, the reaction includes: and 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 step S3, the reaction includes: and (3) reacting for 6-18 h in a mixed reaction system of 2, 6-lutidine and dichloromethane.
In a third aspect, the present application provides an epoxy resin cure indicating composition comprising: colorless transparent epoxy resin, colorless transparent epoxy resin curing agent and epoxy resin curing indicating 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 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 indication compound, a preparation method and a composition thereof, wherein the epoxy resin curing indication compound can be introduced into an epoxy resin crosslinking network as a chromophore after a three-dimensional crosslinking network of a cured epoxy resin generated by colorless transparent epoxy resin such as bisphenol A epoxy resin and colorless transparent epoxy resin curing agent such as polyoxypropylene triamine, and the epoxy resin curing reaction is carried out, so that the network structure of the cured epoxy resin contains more and more chromophores, and 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 generation of the network structure; and the color of the epoxy resin changes, people can directly observe the epoxy resin through eyes under the condition of not damaging the epoxy resin, and the more red the color of the epoxy resin is observed, the greater the curing degree of the epoxy resin is judged, so that the technical problem that the curing degree of the epoxy resin is not intuitively judged in the prior art is solved.
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 of lack of visual judgment of the curing degree of epoxy resin at present, the application provides an epoxy resin curing indication compound, the structure of which is shown as a formula I; in a three-dimensional crosslinked network of the generated cured epoxy resin, the epoxy resin curing indication compound can be introduced into the epoxy resin crosslinked network as a chromophore, and the chromophore can absorb light with a certain wavelength in light, but not absorb light with another wavelength, so that the cured epoxy resin containing the chromophore shows a corresponding color of the absorption wavelength, and the color of the cured epoxy resin is darker and darker as the curing reaction of the epoxy resin is carried out; people can directly observe the color of the cured epoxy resin through eyes, so that the degree of curing of the epoxy resin is judged, the lighter the color is, the smaller the degree of curing of the epoxy resin is, the darker the color is, and the larger the degree of curing of the epoxy resin is; meanwhile, the problem that the epoxy resin sample needs to be destroyed due to the fact that additional instruments and equipment are needed for performance tests such as a differential scanning calorimeter, toughness, hardness, bending strength and bending modulus is avoided, and the defect that the curing degree of the epoxy resin is lack of visual judgment 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 as follows: 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, in the epoxy resin curing indication composition provided by the application, the volume ratio of the colorless transparent epoxy resin to the colorless transparent epoxy resin curing agent is 100: 30-60 parts; and diluting solvent components such as butanediol diglycidyl ether, C13-C15-glycidyl ether and benzyl alcohol are also added.
Preferably, the application also utilizes the relation between the curing degree and the color change of the epoxy resin curing indication composition to establish a quantification method of the curing degree of the epoxy resin; considering that the curing time has a great influence on the curing of the epoxy resin, the quantitative relation between the curing time and the color change in the curing degree of the epoxy resin is established, and specifically, the curing time of the epoxy resin is determined according to the color 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 the mixture was stirred and mixed at room temperature for 12 hours to obtain 2- (ethyl {4- [ (1Z) - (4-nitrophenyl) ethanyl ] phenyl } amino) ethyl hexahydropyridine-4-carboxylic acid;
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
The epoxy resin curing indication composition is placed 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, in 10-30 min, the absorption peak of the absorption spectrum is red shifted, the absorption peak of the epoxy resin is about 650nm in 30min, 40min and 60min, which means that the epoxy resin is cured for 30-60 min to be red in color, the absorption peak of the epoxy resin after being cured for 60min is higher, the absorption to the wavelength about 650nm is stronger, and the red is deeper; further referring to Table 1, it can be seen that as the curing time of the epoxy resin curing indicating composition is prolonged, the absorbance at 650nm is gradually increased, indicating a gradual darkening of red; this shows that the combination of the compound shown in formula I and the group (amine or alcohol) generated in the cross-linked network after bisphenol A epoxy resin curing in the epoxy resin curing indication composition provided by the application generates a wavelength color capable of absorbing about 650nm, and corresponds to the wavelength of red light, so that the cured epoxy resin gradually changes from colorless to pale red, gradually changes from pale red to red, and then changes into 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 process was first fitted to the cure time and absorbance in table 1, and the results are shown in fig. 4, and the obtained linear relationship is: y=0.0275 x-0.165, r 2 = 0.9494.
When an epoxy resin curing indicating composition of the same formulation as in example 2 was cured in a constant temperature oven at 80℃for a certain period of time, the absorbance of the epoxy resin curing indicating composition was measured by an ultraviolet-visible-near infrared spectrometer, and then, according to the following: y=0.0275 x to 0.165 for determining the approximate curing time of the epoxy resin curing indicator composition, the present embodiment can determine the curing time of the epoxy resin more precisely by a linear relationship between the curing time and the absorbance established in advance.
The above embodiments are only for illustrating the technical solution of the present application, and not for limiting the same; although the application has been described in detail with reference to the foregoing embodiments, it will be understood by those of ordinary skill in the art that: the technical scheme described in the foregoing embodiments can be modified or some or all of the technical features thereof can be replaced by equivalents; such modifications and substitutions do not depart from the spirit of the application.
Claims (10)
1. An epoxy resin curing indicating compound is characterized in that the chemical structure is shown as a formula I;
A formula I;
In formula I, et is selected from alkyl.
2. The epoxy resin curing indicating compound according to claim 1, wherein the alkyl group is selected from any one of methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, pentyl, and hexyl.
3. A method for producing an epoxy resin curing indicating compound according to any one of claims 1 to 2, 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.
4. A method for producing an epoxy resin curing indicating compound according to claim 3, wherein in step S1, the process of the reaction comprises: and (3) reacting for 6-18 h in a mixed reaction system of 4-dimethylaminopyridine, dichloromethane and 1-ethyl- (3-dimethylaminopropyl) carbodiimide.
5. A method for producing an epoxy resin curing indicating compound according to claim 3, wherein in step S2, the process of the reaction comprises: and reacting for 4-8 hours in a mixed reaction system of diisopropylethylamine, benzotriazole-N, N, N ', N' -tetramethylurea hexafluorophosphate and N, N-dimethylformamide.
6. A method for producing an epoxy resin curing indicating compound according to claim 3,
Wherein in step S3, the reaction process includes: and (3) reacting for 6-18 h in a mixed reaction system of 2, 6-lutidine and dichloromethane.
7. An epoxy resin cure-indicating composition comprising: a colorless transparent epoxy resin, a colorless transparent epoxy resin curing agent, and an epoxy resin curing indicating compound according to any one of claims 1 to 2.
8. An epoxy resin curing indicating composition according to claim 7, wherein,
The epoxy resin curing indicating composition according to any one of claims 1 to 2, wherein the epoxy resin curing indicating compound is contained in an amount of 0.005% to 0.015% (V/V).
9. The epoxy resin curing indicating composition of claim 7, wherein the colorless transparent epoxy resin is selected from bisphenol a type epoxy resins and the colorless transparent epoxy resin curing agent is selected from polyoxypropylene triamine.
10. Use of an epoxy cure indicating composition according to any one of claims 7-9 for determining epoxy cure.
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Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070191520A1 (en) * | 2004-03-31 | 2007-08-16 | Nichiban Company Limited | Photo-radically curable resin composition containing epoxy resin |
| EP2295487A1 (en) * | 2009-09-11 | 2011-03-16 | Elantas GMBH | Epoxy resin curing indicator composition |
| 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 |
| US20140171552A1 (en) * | 2011-08-24 | 2014-06-19 | Henkel Ag & Co. Kgaa | Indicator for cure of two-component-epoxy adhesives |
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Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20070191520A1 (en) * | 2004-03-31 | 2007-08-16 | Nichiban Company Limited | Photo-radically curable resin composition containing epoxy resin |
| EP2295487A1 (en) * | 2009-09-11 | 2011-03-16 | Elantas GMBH | Epoxy resin curing indicator composition |
| CN102498147A (en) * | 2009-09-11 | 2012-06-13 | 亚兰特斯有限公司 | Epoxy resin curing indicator composition |
| 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 |
| US20140171552A1 (en) * | 2011-08-24 | 2014-06-19 | Henkel Ag & Co. Kgaa | Indicator for cure of two-component-epoxy adhesives |
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