CN111735738A - Method for determining crystallization tendency of liquid epoxy resin - Google Patents
Method for determining crystallization tendency of liquid epoxy resin Download PDFInfo
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- CN111735738A CN111735738A CN202010625123.XA CN202010625123A CN111735738A CN 111735738 A CN111735738 A CN 111735738A CN 202010625123 A CN202010625123 A CN 202010625123A CN 111735738 A CN111735738 A CN 111735738A
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Abstract
The invention belongs to a technology for determining crystallization tendency, and particularly relates to a method for determining the crystallization tendency of liquid epoxy resin. The invention provides a method for measuring the crystallization tendency of liquid epoxy resin, which at least comprises the following steps: s1: placing the liquid epoxy resin in a transparent container, preserving the liquid epoxy resin in an oven at a constant temperature, and cooling the liquid epoxy resin to room temperature; s2: dispersing the liquid epoxy resin cooled in the step S1; s3: refrigerating and storing the dispersed liquid epoxy resin obtained in the step S2; s4: the liquid epoxy resin after the refrigeration storage in the step S3 was returned to room temperature, and the state of the liquid epoxy resin was observed. The method for determining the crystallization tendency of the liquid epoxy resin is convenient and quick, avoids human errors caused by manual mixing, has low crystallization speed, and can simultaneously distinguish the crystallization resistance of various liquid epoxy resins at a specified time point.
Description
Technical Field
The invention belongs to a technology for determining crystallization tendency, and particularly relates to a method for determining the crystallization tendency of liquid epoxy resin.
Background
The epoxy resin is usually used in a liquid state, and the liquid epoxy resin has a small shrinkage rate during a curing reaction, and a cured product thereof is excellent in adhesiveness, heat resistance, chemical resistance, mechanical properties and electrical properties. Liquid epoxy resins are all supercooled liquids at room temperature and have a natural tendency to crystallize, which depends on the purity of the resin, the viscosity of the resin, additives, moisture content and temperature history. Crystallization of liquid epoxy resins is difficult to predict and completely eliminate, and it is particularly important to determine whether the liquid epoxy resin has good or bad crystallization resistance by measuring the crystallization tendency of the liquid epoxy resin.
At present, the determination method of the crystallization tendency of the liquid epoxy resin is ISO 4895-2014, but calcium carbonate and ethanol are added into the liquid epoxy resin, so that a large amount of solid impurities and additives are introduced, and the liquid epoxy resin is a seed crystal for rapid crystallization of the liquid epoxy resin, so that the crystallization speed of the liquid epoxy resin is too high, and the crystallization resistance of various liquid epoxy resins is not convenient to accurately distinguish; meanwhile, the calcium carbonate and the ethanol are added by manual stirring, and different stirring methods can cause different mixing degrees, so that human errors are large. Secondly, the ISO 4895-2014 method is to determine the crystallization degree by observing the fluidity of the liquid resin through tilting the container, and after the calcium carbonate is added and mixed with the liquid epoxy resin, the viscosity of the mixture is much higher than the viscosity of the resin, so that the crystallization resistance of different liquid epoxy resins cannot be determined at a specified time point.
Therefore, the invention needs to research a method for determining crystallization tendency of liquid epoxy resin, which is characterized by convenience, rapidness, accurate distinguishing of crystallization resistance of various liquid epoxy resins at a specified time and no human error.
Disclosure of Invention
In order to solve the above technical problems, a first aspect of the present invention provides a method for determining a crystallization tendency of a liquid epoxy resin, comprising at least the steps of:
s1: placing the liquid epoxy resin in a transparent container, preserving the liquid epoxy resin in an oven at a constant temperature, and cooling the liquid epoxy resin to room temperature;
s2: dispersing the liquid epoxy resin cooled in the step S1;
s3: refrigerating and storing the dispersed liquid epoxy resin obtained in the step S2;
s4: the liquid epoxy resin after the refrigeration storage in the step S3 was returned to room temperature, and the state of the liquid epoxy resin was observed.
As a preferable technical scheme, the constant temperature in the step S1 is 40-80 ℃.
As a preferable technical scheme, the constant-temperature storage time in the step S1 is 6-36 h.
As a preferred technical solution, the dispersing manner in the step S2 is spatula stirring or shaking.
As a preferable technical scheme, the stirring time of the tongue depressor is 0.5-15 min; the shaking table time is 5-50 min.
As a preferable technical scheme, the temperature of the refrigeration preservation in the step S3 is-2-12 ℃.
As a preferable technical solution, in the step S4, if the liquid epoxy resin is not crystallized after returning to room temperature, the step S2 is repeated.
As a preferred technical solution, the state of the liquid epoxy resin is: clear without turbidity, with turbidity but can flow, can not flow completely into solid state.
As a preferable technical scheme, the liquid epoxy resin is selected from one or more of bisphenol A type liquid epoxy resin CYD127, bisphenol A type liquid epoxy resin NPEL-127E, Hexion waterborne epoxy resin 035C, south Asia epoxy resin DER383, Dasheng epoxy resin TS-180 and Dasheng epoxy resin 190.
The second aspect of the present invention provides an application of the method for determining crystallization tendency as described above in the fields of purity analysis, viscosity control, additive type and content analysis, and moisture content analysis of liquid epoxy resins.
Has the advantages that: according to the method for determining the crystallization tendency of the liquid epoxy resin, calcium carbonate and ethanol are not added, so that the method is convenient and rapid, and human errors caused by manual mixing are avoided; meanwhile, the crystallization speed is low because no seed crystal for quickly crystallizing the liquid epoxy resin is available, so that the crystallization resistance of various liquid epoxy resins can be distinguished conveniently. The method for measuring the crystallization tendency of the liquid epoxy resin provided by the invention judges the crystallization state of the resin by observing the transparency degree of the liquid epoxy resin, and can distinguish the crystallization resistance of various liquid epoxy resins at a specified time point.
Detailed Description
The technical features of the technical solutions provided by the present invention are further clearly and completely described below with reference to the specific embodiments, and the scope of protection is not limited thereto.
The words "preferred", "more preferred", and the like, in the present invention refer to embodiments of the invention that may provide certain benefits, under certain circumstances. However, other embodiments may be preferred, under the same or other circumstances. Furthermore, the recitation of one or more preferred embodiments does not imply that other embodiments are not useful, nor is it intended to exclude other embodiments from the scope of the invention.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
Approximating language, as used herein throughout the specification and claims, is intended to modify a quantity, such that the invention is not limited to the specific quantity, but includes portions that are literally received for modification without substantial change in the basic function to which the invention is related. Accordingly, the use of "about" to modify a numerical value means that the invention is not limited to the precise value. In some instances, the approximating language may correspond to the precision of an instrument for measuring the value. In the present description and claims, range limitations may be combined and/or interchanged, including all sub-ranges contained therein if not otherwise stated.
In addition, the indefinite articles "a" and "an" preceding an element or component of the invention are not intended to limit the number requirement (i.e., the number of occurrences) of the element or component. Thus, "a" or "an" should be read to include one or at least one, and the singular form of an element or component also includes the plural unless the stated number clearly indicates that the singular form is intended.
In order to solve the above technical problems, a first aspect of the present invention provides a method for determining a crystallization tendency of a liquid epoxy resin, comprising at least the steps of:
s1: placing the liquid epoxy resin in a transparent container, preserving the liquid epoxy resin in an oven at a constant temperature, and cooling the liquid epoxy resin to room temperature;
s2: dispersing the liquid epoxy resin cooled in the step S1;
s3: refrigerating and storing the dispersed liquid epoxy resin obtained in the step S2;
s4: the liquid epoxy resin after the refrigeration storage in the step S3 was returned to room temperature, and the state of the liquid epoxy resin was observed.
In one embodiment, the constant temperature in the step S1 is 40-80 ℃; preferably, the constant temperature in the step S1 is 50-70 ℃; more preferably, the constant temperature in the step S1 is any one of 50 ℃, 55 ℃, 60 ℃ and 70 ℃.
In one embodiment, the constant temperature preservation time in the step of S1 is 6-36 h; preferably, the constant-temperature storage time in the step S1 is 8-24 h; more preferably, the time for constant-temperature storage in the step S1 is any one of 8h, 16h, 20h and 24 h.
In one embodiment, the dispersing in step S2 is performed by spatula stirring or shaking.
In one embodiment, the time for stirring the tongue depressor is 0.5-15 min; preferably, the stirring time of the tongue depressor is 1-5 min; more preferably, the stirring time of the tongue depressor is 1-3 min; more preferably, the time for stirring the tongue depressor is any one of 1min, 2min and 3 min.
In one embodiment, the shaking table is used for a period of 5 to 50 min; preferably, the shaking table time is 5-30 min.
In a preferred embodiment, the dispersing in the step of S2 is performed by stirring with a spatula for 1-3 min.
In one embodiment, the temperature for cold storage in the step S3 is-2-12 deg.C; preferably, the temperature for cold storage in the step S3 is 0-10 ℃; more preferably, the temperature of the cold storage preservation in the step S3 is 2-8 ℃; more preferably, the temperature for cold storage preservation in the step S3 is 5-8 ℃; more preferably, the temperature for cold storage in the step S3 is any one of 5 ℃, 7 ℃ and 8 ℃.
In one embodiment, if the liquid epoxy resin is not crystallized after returning to room temperature in the S4 step, the S2 step is repeated.
The step S4 is performed by taking out the epoxy resin from the refrigerator, observing the state of the liquid epoxy resin after the temperature of the liquid epoxy resin is returned to room temperature, and repeating the step S2 if the liquid epoxy resin is not crystallized.
The invention judges the crystallization state of the liquid epoxy resin by observing the transparency degree of the liquid epoxy resin. The transparency of the liquid epoxy resin was observed twice a day.
The invention divides the crystallization degree of the liquid epoxy resin into three states, and the states are recorded according to different degrees during observation. And a state A: the liquid epoxy resin is still clear and has no turbidity; and a state B: cloudiness occurs and can flow; and C, state C: and cannot flow completely into a solid state.
In one embodiment, the state of the liquid epoxy resin is: clear without turbidity, with turbidity but can flow, can not flow completely into solid state.
In the present invention, the flow is judged based on the state after the liquid epoxy resin is left horizontally for 1 minute.
In one embodiment, the liquid epoxy resin is selected from one or more of bisphenol A type liquid epoxy resin CYD127, bisphenol A type liquid epoxy resin NPEL-127E, Hexion waterborne epoxy resin 035C, south Asia epoxy resin DER383, Dasheng epoxy resin TS-180, Dasheng epoxy resin 190;
preferably, the liquid epoxy resin is selected from one or more of bisphenol A type liquid epoxy resin NPEL-127E, Hexion waterborne epoxy resin 035C, south Asia epoxy resin DER383, Dasheng epoxy resin TS-180 and Dasheng epoxy resin 190.
The bisphenol A type liquid epoxy resin NPEL-127E was purchased from Vast science and technology Limited; the Hexion waterborne epoxy resin 035C was purchased from Vast Saisen (HEXION) chemical Limited, USA; the south Asian epoxy DER383 was purchased from Dow chemical company; the Daosheng synthetic epoxy resin TS-180 and the Daosheng synthetic epoxy resin 190 are purchased from Daosheng synthetic materials science and technology (Shanghai) Co., Ltd.
Epoxy resin is a thermosetting plastic which forms a three-dimensional network structure when reacted with a curing agent. The epoxy resin is usually used in a liquid state, and the liquid epoxy resin has a small shrinkage rate during a curing reaction, and has characteristics of excellent adhesiveness, heat resistance, chemical resistance, mechanical properties and electrical properties of a cured product.
The common liquid epoxy resin belongs to supercooled liquid at room temperature. The supercooled liquid has reached the freezing point of the liquid epoxy resin at room temperature, but remains in a liquid state, and has a natural tendency to crystallize. Crystallization of liquid epoxy resin is similar to other crystal growths, and its crystallization tendency depends on the purity of the liquid epoxy resin, the viscosity of the liquid epoxy resin, additives, moisture content, and temperature history.
The inventor finds that in the process of completing the research of the invention, by adopting the technical scheme of the invention, the liquid epoxy resin is firstly placed in a transparent container and is preserved for 8-24 hours in an oven at the constant temperature of 50-70 ℃, and then is cooled to the room temperature; then stirring the cooled liquid epoxy resin for 1-3min by using a tongue depressor; then refrigerating and storing the stirred liquid epoxy resin at 5-8 ℃; and finally, the refrigerated and stored liquid epoxy resin is restored to the room temperature, the crystallization state of the liquid epoxy resin is judged by observing the transparency degree of the liquid epoxy resin, and the crystallization resistance of various liquid epoxy resins can be distinguished at the same time at a specified time point without adding calcium carbonate and ethanol. The reason the inventor guesses may be that the liquid epoxy resin is heated and then cooled to room temperature, stirred, then refrigerated and stored, and then the room temperature is recovered, and the crystallization state of the liquid epoxy resin is judged by observing the transparency degree of the liquid epoxy resin, so that the convenience and the rapidness are realized; and the liquid epoxy resin is preserved for 8-24h at a constant temperature of 50-70 ℃ in an oven, is cooled to room temperature, is stirred for 1-3min by a tongue depressor, is preserved at a refrigeration temperature of 5-8 ℃ to ensure that the liquid epoxy resin is crystallized and has a lower crystallization speed, so that the crystallization resistance of various liquid epoxy resins can be accurately distinguished, and meanwhile, the crystallization resistance of various liquid epoxy resins can be accurately distinguished at a specified time point by judging the crystallization state of the resin by observing the transparency degree of the liquid epoxy resin. Furthermore, the inventors have surprisingly found that the present invention employs a measurement method that does not incorporate calcium carbonate and ethanol as compared to the ISO 4895-2014 method. Firstly, the invention does not add a large amount of solid impurities and additives, improves the purity of the liquid epoxy resin, ensures that the shrinkage rate of the liquid epoxy resin is small in the curing reaction process, and ensures that the liquid epoxy resin has the characteristics of excellent adhesiveness, heat resistance, chemical resistance, mechanical property and electrical property of a cured product and is not influenced. Secondly, the crystallization speed is high due to the fact that calcium carbonate is used as a crystal seed of the liquid epoxy resin crystal growth to induce and form the liquid epoxy resin crystal which is propagated subsequently, the crystallization speed is low, and the crystallization resistance of various liquid epoxy resins can be accurately distinguished. Moreover, the method adopts the tongue depressor to stir for 1-3min without human error, and does not add calcium carbonate and ethanol and does not need manual stirring, so that the method effectively avoids the error of detection results caused by different mixing degrees due to different stirring methods in manual stirring. Finally, the crystallization degree of the liquid epoxy resin is judged by observing the transparency degree of the liquid epoxy resin instead of observing the fluidity of the liquid epoxy resin by inclining the container, the viscosity is not increased due to the mixing of the calcium carbonate and the liquid epoxy resin, and the crystallization resistance of different liquid epoxy resins can be judged at a specified time point.
The second aspect of the present invention provides an application of the method for determining crystallization tendency as described above in the fields of purity analysis, viscosity control, additive type and content analysis, and moisture content analysis of liquid epoxy resins.
The present invention will be specifically described below by way of examples. It should be noted that the following examples are only for illustrating the present invention and should not be construed as limiting the scope of the present invention, and that the insubstantial modifications and adaptations of the present invention by those skilled in the art based on the above disclosure are still within the scope of the present invention.
In addition, the starting materials used are all commercially available, unless otherwise specified.
Examples
In the examples, the bisphenol A type liquid epoxy resin NPEL-127E was purchased from Vast science and technology Limited; the Hexion waterborne epoxy resin 035C was purchased from Vast Saisen (HEXION) chemical Limited, USA; the south Asian epoxy DER383 was purchased from Dow chemical company; the Daosheng synthetic epoxy resin TS-180 and the Daosheng synthetic epoxy resin 190 are purchased from Daosheng synthetic materials science and technology (Shanghai) Co., Ltd.
Example 1
Example 1 provides a method for determining the tendency of a liquid epoxy resin to crystallize, the steps comprising: putting the Dasheng natural epoxy resin TS-180 (abbreviated as 180), the Dasheng natural epoxy resin 190 (abbreviated as 190) and the Hexion water-based epoxy resin 035C (abbreviated as 035C) into a transparent container, putting the transparent container into an oven at 70 ℃, keeping the temperature for 16h, taking out the transparent container from the oven, and cooling the transparent container to room temperature; cooling, and stirring with a spatula at a stirring speed of 50rpm for 2 min; stirring, and storing in a refrigerator at 5 deg.C for 8 h; and taking out the epoxy resin from the refrigerator, recovering the epoxy resin to room temperature, judging the crystallization state of the liquid epoxy resin by observing the transparency degree of the liquid epoxy resin, and repeating the stirring step if no crystallization exists. The results of the measurements are recorded, see table 1; the time interval from the first appearance of the a state to the first appearance of the B state, and the time interval from the first appearance of the a state to the first appearance of the C state were calculated for each liquid epoxy resin, and the calculation results are shown in table 2.
Table 1 state of liquid epoxy resin as described in example 1
TABLE 2 time intervals for the A-B, A-C state of the liquid epoxy resin described in example 1
| Change of state | 180222-1 | 180222-5 | 180326-1 | 180326-2 | 180 | 190 | 035C |
| A-B | 14d | 23d+8h | 15d | 23d+8h | 11d | 14d | >24d |
| A-C | 23d+8h | >24d | >24d | >24d | 15d | >24d | / |
Comparative example 1
Comparative example 1 the tendency of crystallization of a Dacron natural epoxy resin TS-180 (abbreviated as 180), Hexion waterborne epoxy resin 035C (abbreviated as 035C), bisphenol A type liquid epoxy resin NPEL-127E (abbreviated as 127E), south Asia epoxy resin DER383 (abbreviated as DER383) liquid epoxy resin was determined by the method of ISO 4895-2014 (with CaCO3 added). The results of the measurements are recorded, see table 3; the time interval from the first appearance of the a state to the first appearance of the B state, and the time interval from the first appearance of the a state to the first appearance of the C state were calculated for each liquid epoxy resin, and the calculation results are shown in table 4.
Table 3 status of liquid epoxy resin as described in comparative example 1
TABLE 4 time intervals for the A-B, A-C state of the liquid epoxy resin described in comparative example 1
| Change of state | 180 | 035C | 127E | DER383 |
| A-B | 2d | >17d | >(1d +8h) and<2d | 2d |
| A-C | 3d+6h+40min | / | 2d | 2d+8h |
the foregoing examples are merely illustrative and serve to explain some of the features of the method of the present invention. The appended claims are intended to claim as broad a scope as is contemplated, and the examples presented herein are merely illustrative of selected implementations in accordance with all possible combinations of examples. Accordingly, it is applicants' intention that the appended claims are not to be limited by the choice of examples illustrating features of the invention. Also, where numerical ranges are used in the claims, subranges therein are included, and variations in these ranges are also to be construed as possible being covered by the appended claims.
Claims (10)
1. A method for measuring the crystallization tendency of liquid epoxy resin is characterized by at least comprising the following steps:
s1: placing the liquid epoxy resin in a transparent container, preserving the liquid epoxy resin in an oven at a constant temperature, and cooling the liquid epoxy resin to room temperature;
s2: dispersing the liquid epoxy resin cooled in the step S1;
s3: refrigerating and storing the dispersed liquid epoxy resin obtained in the step S2;
s4: the liquid epoxy resin after the refrigeration storage in the step S3 was returned to room temperature, and the state of the liquid epoxy resin was observed.
2. The method for determining the tendency to crystallize according to claim 1, wherein the constant temperature in the step of S1 is 40 to 80 ℃.
3. The method for determining the tendency to crystallize according to claim 2, wherein the holding time at constant temperature in the step S1 is 6 to 36 hours.
4. The method for determining the tendency to crystallize according to claim 1, wherein the dispersion in step S2 is performed by spatula stirring or shaking.
5. A method for determining the tendency to crystallize according to claim 4, characterized in that the stirring time of the tongue depressor is 0.5-15 min; the shaking table time is 5-50 min.
6. The method for determining the tendency to crystallize according to claim 1, wherein the temperature at which the cold storage of step S3 is maintained is-2 to 12 ℃.
7. The method for measuring the tendency to crystallize according to any one of claims 1 to 6, wherein in the step S4, if the liquid epoxy resin does not crystallize after returning to room temperature, the step S2 is repeated.
8. The method for determining the tendency to crystallize according to any one of claims 1 to 6, wherein the state of the liquid epoxy resin is: clear without turbidity, with turbidity but can flow, can not flow completely into solid state.
9. The method for determining the tendency to crystallize according to any one of claims 1 to 6, wherein the liquid epoxy resin is selected from one or more of bisphenol A liquid epoxy resin CYD127, bisphenol A liquid epoxy resin NPEL-127E, Hexion aqueous epoxy resin 035C, south Asia epoxy resin DER383, Dasheng epoxy resin TS-180, and Dasheng epoxy resin 190.
10. Use of the method for determining the tendency to crystallize according to any one of claims 1 to 9 in the fields of purity analysis, viscosity control, analysis of the type and content of additives, and analysis of the moisture content of liquid epoxy resins.
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| CN1106420A (en) * | 1993-08-20 | 1995-08-09 | 国际壳牌研究有限公司 | Liquid epoxy resin composition |
| US20020123602A1 (en) * | 2000-12-28 | 2002-09-05 | Japan Epoxy Resins Co., Ltd. | Crystallized epoxy resins, their production method, and curable compositions comprising them |
| CN1816580A (en) * | 2003-02-03 | 2006-08-09 | 新日铁化学株式会社 | Epoxy resin, process for producing the same, epoxy resin composition containing the same, and cured object |
| CN104066765A (en) * | 2011-11-01 | 2014-09-24 | 陶氏环球技术有限责任公司 | Liquid epoxy resin formulations |
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2020
- 2020-07-01 CN CN202010625123.XA patent/CN111735738A/en active Pending
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1106420A (en) * | 1993-08-20 | 1995-08-09 | 国际壳牌研究有限公司 | Liquid epoxy resin composition |
| US20020123602A1 (en) * | 2000-12-28 | 2002-09-05 | Japan Epoxy Resins Co., Ltd. | Crystallized epoxy resins, their production method, and curable compositions comprising them |
| CN1816580A (en) * | 2003-02-03 | 2006-08-09 | 新日铁化学株式会社 | Epoxy resin, process for producing the same, epoxy resin composition containing the same, and cured object |
| CN104066765A (en) * | 2011-11-01 | 2014-09-24 | 陶氏环球技术有限责任公司 | Liquid epoxy resin formulations |
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