CN115436505A - Quantitative test method for polyester biodegradable material - Google Patents
Quantitative test method for polyester biodegradable material Download PDFInfo
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- CN115436505A CN115436505A CN202210946873.6A CN202210946873A CN115436505A CN 115436505 A CN115436505 A CN 115436505A CN 202210946873 A CN202210946873 A CN 202210946873A CN 115436505 A CN115436505 A CN 115436505A
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- G—PHYSICS
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Abstract
The application provides a quantitative test method of a polyester biodegradable material, which comprises the following steps: preparing an ester exchange solution, preparing a standard solution, pretreating a sample, analyzing the content of a compound to be detected in the liquid to be detected by adopting a gas chromatography-mass spectrometer, calculating the polyester content in the sample to be detected according to an alcoholysis product to realize quantitative test on the polyester biodegradable material, measuring the type and the content of each polyester material in the sample to be detected, and carrying out quantitative analysis on polymers with relatively close properties.
Description
Technical Field
The application relates to the technical field of biodegradation, in particular to a quantitative test method for a polyester biodegradable material.
Background
Plastics permeate daily life of people with convenience, and meanwhile, huge environmental problems are brought, biodegradable plastic products are produced at the same time for solving the problems, and the degradation performance of the plastic products mainly depends on the components of the biodegradable plastic products. Therefore, if the specific content of biodegradable components in the plastic product is known, the degradation performance and the final biodegradation rate can be estimated.
At present, most of the existing methods for quantifying each polymer in a high molecular material are separation-gravimetric methods, i.e. according to the different solubilities of different types of polymers in different solvents, the measured polymer is separated and then weighed to analyze the content of the polymer. The method is more suitable for analyzing the content of the polymers in the mixed polymers with larger property difference, but for the analysis of the same kind of polymers, a proper solvent is difficult to find for analyzing the content of each polymer, so that the existing quantitative test method is difficult to be suitable for the quantitative analysis of the polymers with closer properties.
Disclosure of Invention
The application provides a quantitative test method of a polyester biodegradable material, which can carry out quantitative analysis on polymers with relatively close properties.
In order to achieve the above technical effects, the present application provides a method for quantitatively testing a polyester biodegradable material, comprising:
preparing a transesterification solution: adding toluene into zinc acetate dihydrate, fixing the volume with methanol, and shaking up to obtain an ester exchange solution;
preparing a standard solution: preparing a mixed standard solution containing methyl glycolate, methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate, dimethyl succinate, dimethyl adipate, 6-caprolactone, 1, 4-butanediol, methyl 6-hydroxycaproate, dimethyl terephthalate and toluene, and drawing a corresponding standard curve;
sample pretreatment: weighing a sample to be detected in a stainless steel reaction kettle, adding the ester exchange solution, covering and sealing, placing in an oven at 140-220 ℃ until the polyester reaction is complete, cooling, absorbing the solution, filtering, and diluting with methanol to obtain a liquid to be detected;
analyzing the sample, namely analyzing the content of the compound to be detected in the liquid to be detected by using a gas chromatography mass spectrometer;
and (4) analyzing results: and calculating the polyester content in the sample to be detected according to the alcoholysis product.
In one embodiment, the formulated transesterification solution further comprises: adding 0.0542ml-0.5420ml toluene into 10mg zinc acetate dihydrate, diluting to constant volume with methanol, and shaking to obtain ester exchange solution;
the sample pretreatment further comprises: weighing 0.01g to 0.10g of sample to be detected in a stainless steel reaction kettle, adding 25ml of the ester exchange solution, covering and sealing, placing in an oven at the temperature of 140 ℃ to 220 ℃, reacting for 2 to 3 hours until the polyester reaction is complete, cooling, absorbing the solution, filtering, and diluting by 25 times by using methanol to obtain the liquid to be detected.
In one embodiment, the curve points of the standard curve are respectively: 1mg/L, 2mg/L, 5mg/L, 10mg/L, 20mg/L, 50mg/L and 100mg/L.
In one embodiment, the toluene concentration is 10mg/L to 100mg/L.
In one embodiment, the result analysis further comprises:
calculating the polyester content in the sample to be detected based on a first formula, wherein the first formula is as follows:
wherein, c Polyester The content of polyester in the material, V is the volume of alcoholysis liquid, f is the dilution factor of the alcoholysis liquid during test, c i Measured concentration of dibasic acid dimethyl ester or hydroxy carboxylic acid methyl ester in alcoholysis solution, M i Is the relative molecular mass, M, of the dibasic acid dimethyl ester or the hydroxy carboxylic acid methyl ester in the alcoholysis solution i1 Is the relative molecular mass, M, of the dibasic acid or hydroxycarboxylic acid corresponding to the product in the alcoholysis solution i2 Is the relative molecular mass of dihydric alcohol in the polyester, n is the dehydration number in the polycondensation process, when the ester product in the alcoholysis solution is dibasic acid or dihydric alcohol polyester, n is 2 correspondingly, when the ester product in the alcoholysis solution is hydroxycarboxylic acid polyester, n is 1 water Is the relative molecular mass of water, and m is the sample of the test procedureThe product mass is 10 as conversion coefficient.
Therefore, the quantitative test method for the polyester biodegradable material disclosed by the scheme of the application realizes the quantitative test of the polyester biodegradable material by preparing the ester exchange solution, preparing the standard solution, pretreating the sample, analyzing the content of the compound to be tested in the solution to be tested by adopting the gas chromatography mass spectrometer and calculating the polyester content in the sample to be tested according to the alcoholysis product, can measure the type and the content of each polyester material in the sample to be tested, and can perform quantitative analysis on the polymer with relatively close properties.
Drawings
In order to more clearly illustrate the technical solutions in the embodiments of the present application, the drawings used in the embodiments or the description of the prior art will be briefly described below. It is obvious that the drawings in the following description are only some embodiments of the application, and that for a person skilled in the art, other drawings can be derived from them without inventive effort.
FIG. 1 is a schematic flow chart illustrating an embodiment of a quantitative testing method for polyester-based biodegradable materials provided herein;
FIG. 2 is a graph of an example test spectrum of the 50mg/L concentration points provided herein.
Detailed Description
In the following description, for purposes of explanation and not limitation, specific details are set forth, such as particular system structures, techniques, etc. in order to provide a thorough understanding of the embodiments of the invention. It will be apparent, however, to one skilled in the art that the present invention may be practiced in other embodiments that depart from these specific details. In other instances, detailed descriptions of well-known systems, devices, circuits, and methods are omitted so as not to obscure the description of the present application with unnecessary detail.
It will be understood that the terms "comprises" and/or "comprising," when used in this specification and the appended claims, specify the presence of stated features, integers, steps, operations, elements, and/or components, but do not preclude the presence or addition of one or more other features, integers, steps, operations, elements, components, and/or groups thereof.
It is also to be understood that the terminology used in the description of the present application is for the purpose of describing particular embodiments only and is not intended to be limiting of the application. As used in the specification of the present application and the appended claims, the singular forms "a," "an," and "the" are intended to include the plural forms as well, unless the context clearly indicates otherwise.
The technical solutions in the embodiments of the present application are clearly and completely described below with reference to the drawings in the embodiments of the present application, and it is obvious that the described embodiments are only a part of the embodiments of the present application, and not all of the embodiments. All other embodiments obtained by a person of ordinary skill in the art based on the embodiments in the present application without making any creative effort belong to the protection scope of the present application.
In the following description, numerous specific details are set forth in order to provide a thorough understanding of the present application, but the present application may be practiced in other ways than those described herein, and it will be apparent to those of ordinary skill in the art that the present application is not limited by the specific embodiments disclosed below.
Example one
The application provides a quantitative test method of polyester biodegradable materials, as shown in fig. 1, the quantitative test method comprises the following steps:
specifically, 10mg of zinc acetate dihydrate is weighed into a 250mL volumetric flask, 0.0542mL to 0.5420mL of toluene is added by using a pipette, the volume is determined by using methanol, and the mixture is shaken up to be used as a transesterification solution.
in the embodiment of the present application, the curve points of the standard curve are respectively: 1mg/L, 2mg/L, 5mg/L, 10mg/L, 20mg/L, 50mg/L and 100mg/L, and toluene is an internal standard substance of the standard solution, and specifically, the concentration of the toluene is 10mg/L-100mg/L. It is understood that, when the curve point of the calibration curve is 1mg/L, the concentrations of methyl glycolate, methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate, dimethyl succinate, dimethyl adipate, 6-caprolactone, 1, 4-butanediol, methyl 6-hydroxycaproate and dimethyl terephthalate are all 1mg/L.
In the present embodiment, a mixed standard solution having a preparation curve point of 1mg/L, 2mg/L, 5mg/L, 10mg/L, 20mg/L, 50mg/L and 100mg/L in the preparation order of a stock solution, an intermediate solution and a standard solution is used, methyl glycolate, methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate, dimethyl succinate, dimethyl adipate, 6-caprolactone, 1, 4-butanediol, methyl 6-hydroxycaproate, dimethyl terephthalate and toluene, and the toluene concentration corresponds to the toluene volume added at the time of preparing an ester exchange solution, for example, when the toluene volume added at the time of preparing an ester exchange solution is 0.0542mL, the corresponding toluene concentration is 10mg/L in the present embodiment; when the amount of toluene added at the time of preparing the transesterification solution was 0.5420mL, the toluene concentration corresponding to this case was 100mg/L.
For example, mixed standard solutions of methyl glycolate, methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate, dimethyl succinate, dimethyl adipate, 6-caprolactone, 1, 4-butanediol, methyl 6-hydroxycaproate, dimethyl terephthalate, and toluene at concentrations of 1mg/L, 2mg/L, 5mg/L, 10mg/L, 20mg/L, 50mg/L, and 100mg/L, respectively, are prepared, wherein the toluene concentration is 100mg/L, the test spectrum of the specific 50mg/L concentration point is shown in FIG. 2, standard curves are drawn according to the test results, and the parameters (y = ax + b) of each standard curve are shown in Table 1.
TABLE 1
It should be noted that most of the biodegradable materials are polyester-based polymers, such as poly (terephthalic acid)/adipic acid/butylene succinate (PBAT), poly (lactic acid) (PLA), polyglycolide (PGA), polybutylene succinate (PBS), polybutylene succinate/adipate (PBSA), polycaprolactone (PCL), etc., in the present application, methanol is used as a solvent and a reactant, and complete conversion of polyester can be achieved under the catalysis of zinc acetate and an excessive alcohol-ester ratio.
Weighing 0.01g to 0.10g of sample to be detected in a stainless steel reaction kettle, adding 25ml of the ester exchange solution, covering and sealing, placing in an oven at 140 ℃ to 220 ℃, reacting for 2 to 3 hours until the polyester reaction is complete, cooling, absorbing the solution, filtering, and diluting by 25 times by using methanol to obtain the liquid to be detected.
104, analyzing a sample, namely analyzing the content of a compound to be detected (an ester product) in the liquid to be detected by using a gas chromatography mass spectrometer;
in the examples of the present application, the gas chromatography-mass spectrometry (GC-MS) is used to quantitatively test various transesterification products, and has both qualitative and quantitative effects on the analysis of the polyester-based biodegradable material, specifically, the following analysis conditions are used to analyze the content of the compound to be tested in the test solution, as shown in table 2, where table 2 is the sample analysis conditions of the examples of the present application.
TABLE 2
In one embodiment, the result analysis further includes:
calculating the polyester content in the sample to be detected based on a first formula, wherein the first formula is as follows:
wherein, c Polyester The content of polyester in the material, V is the volume of alcoholysis liquid, f is the dilution factor of the alcoholysis liquid during test, c i Measured concentration of dibasic acid dimethyl ester or hydroxy carboxylic acid methyl ester in alcoholysis solution, M i Is the relative molecular mass, M, of the dibasic acid dimethyl ester or the hydroxy carboxylic acid methyl ester in the alcoholysis solution i1 Is the relative molecular mass, M, of the dibasic acid or hydroxycarboxylic acid corresponding to the product in the alcoholysis solution i2 Is the relative molecular mass of dihydric alcohol in the polyester, n is the dehydration number in the polycondensation process, when the ester product in the alcoholysis solution is dibasic acid or dihydric alcohol polyester, n is 2, when the ester product in the alcoholysis solution is hydroxycarboxylic acid polyester, n is 1, M water Is the relative molecular mass of water, m is the sample mass during the test, and 10 is the conversion factor.
It should be noted that, according to the principle of ester exchange reaction, the products of alcoholysis of each polyester material are all dimethyl diacid and corresponding diol, or are their corresponding methyl hydroxycarboxylates. Therefore, the product after the alcoholysis of PLA is methyl lactate, the product after the alcoholysis of PCL is methyl 6-hydroxycaproate, the product after the alcoholysis of PBAT is dimethyl terephthalate, dimethyl adipate and butanediol, the product after the alcoholysis of PBS is dimethyl succinate and butanediol, and the rest of the details can be seen in table 3, where table 3 is a comparison table of common materials and alcoholysis products.
| Serial number | Name(s) | For short | Ester products |
| 1 | Poly (terephthalic acid)/adipic acid/butylene terephthalate | PBAT | Dimethyl terephthalate and |
| 2 | Polylactic acid | PLA | Lactic acid methyl ester |
| 3 | Polyglycolide | PGA | 2-Hydroxyacetic acid methyl ester |
| 4 | Polybutylene succinate | PBS | Succinic acid dimethyl ester |
| 5 | Poly (butylene succinate/adipate) | PBSA | Dimethyl succinate and dimethyl adipate |
| 6 | Polycaprolactone | PCL | 6-Hydroxycaproic acid methyl ester, 6-caprolactone |
| 7 | Poly-3-hydroxybutyrate esters | PHB | 3-Hydroxybutanoic acid methyl ester |
| 8 | Poly-3-hydroxybutyric acid/pentanoate | PHBV | Methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate |
TABLE 3
For example, taking polylactic acid as an example, substituting a polylactic acid related value into a first formula to calculate the content of polylactic acid in a sample to be measured, specifically:
for further understanding, taking PBAT as an example, the PBAT belongs to thermoplastic biodegradable plastics and is a copolymer of butanediol adipate and butanediol terephthalate as an example, the PBAT related value is substituted into a first formula to calculate the content of PBAT in the sample to be detected, and the specific steps are as follows:
on the basis of accurately obtaining the content of the alcoholysis product in the material, the content of the corresponding polyester in the material can be calculated according to the formula.
Therefore, the quantitative test method for the polyester biodegradable material disclosed by the scheme of the application realizes the quantitative test of the polyester biodegradable material by preparing the ester exchange solution, preparing the standard solution, pretreating the sample, analyzing the content of the compound to be tested in the solution to be tested by adopting the gas chromatography mass spectrometer and calculating the polyester content in the sample to be tested according to the alcoholysis product, can measure the type and the content of each polyester material in the sample to be tested, performs quantitative analysis on polymers with relatively similar properties, is simple in overall operation, and is suitable for testers at various levels.
Typical experimental procedures: in order to verify the effectiveness of the method, polylactic acid particles are used as a sample to be tested for testing, the test material is polylactic acid particles, about 0.03g of polylactic acid particles are weighed in a stainless steel reaction kettle, 25mL of ester exchange solution is added, a cover is added for sealing, the mixture is respectively placed in ovens at 140 ℃, 180 ℃ and 220 ℃ for reaction for 3 hours, the polyester reaction is complete, the solution is absorbed after cooling and filtered, and is diluted by 25 times by using methanol, and the mixture is tested by a computer.
The polylactic acid content in the polylactic acid particles was considered to be 100%, and according to the test results, the polylactic acid contents were calculated to be 99.7%, 100.1%, and 100.6%, respectively.
In order to further verify the effectiveness of the method, polybutylene succinate, polycaprolactone and polybutylene succinate/adipate particles are used as samples to be tested for testing, about 0.01g of polylactic acid particles are weighed in three stainless steel reaction kettles respectively, 25mL of ester exchange solution is added, the three stainless steel reaction kettles are covered and sealed, the three stainless steel reaction kettles are placed in a 220 ℃ oven to react for 3 hours, the polyester reaction is complete, the cooled solution is sucked and filtered, the solution is diluted by 25 times by using methanol, and the test is carried out on a machine.
The polylactic acid content in each plastic particle was considered to be 100%, and according to the test results, the contents of the three materials were calculated to be 98.1%, and 99.4%, respectively.
It should be noted that, in the quantitative calculation process of polycaprolactone, the influence of methyl 6-hydroxycaproate and 6-caprolactone on the content needs to be considered at the same time.
The above embodiments are only used to illustrate the technical solutions of the present application, and not to limit the same; although the present application has been described in detail with reference to the foregoing embodiments, it should be understood by those of ordinary skill in the art that: the technical solutions described in the foregoing embodiments may still be modified, or some technical features may be equivalently replaced; such modifications and substitutions do not substantially depart from the spirit and scope of the embodiments of the present application and are intended to be included within the scope of the present application.
Claims (5)
1. A quantitative test method for polyester biodegradable materials is characterized by comprising the following steps:
preparing a transesterification solution: adding toluene into zinc acetate dihydrate, fixing the volume with methanol, and shaking up to obtain an ester exchange solution;
preparing a standard solution: preparing a mixed standard solution containing methyl glycolate, methyl 3-hydroxybutyrate, methyl 3-hydroxypentanoate, dimethyl succinate, dimethyl adipate, 6-caprolactone, 1, 4-butanediol, methyl 6-hydroxycaproate, dimethyl terephthalate and toluene, and drawing a corresponding standard curve;
sample pretreatment: weighing a sample to be detected in a stainless steel reaction kettle, adding the ester exchange solution, covering and sealing, placing in an oven at 140-220 ℃ until the polyester reaction is complete, cooling, absorbing the solution, filtering, and diluting with methanol to obtain a liquid to be detected;
analyzing the sample by using a gas chromatography mass spectrometer to analyze the content of the compound to be detected in the liquid to be detected;
and (4) analyzing results: and calculating the polyester content in the sample to be detected according to the alcoholysis product.
2. The quantitative test method of claim 1,
also included in the formulated transesterification solution are: adding 0.0542ml-0.5420ml toluene into 10mg zinc acetate dihydrate, using methanol to fix the volume, shaking up to obtain ester exchange solution;
the sample pretreatment further comprises: weighing 0.01g to 0.10g of sample to be detected in a stainless steel reaction kettle, adding 25ml of the ester exchange solution, covering and sealing, placing in an oven at 140 ℃ to 220 ℃, reacting for 2 to 3 hours until the polyester reaction is complete, absorbing the solution after cooling, filtering, and diluting by 25 times with methanol to obtain the liquid to be detected.
3. The quantitative test method according to claim 2, wherein the curve points of the standard curve are respectively: 1mg/L, 2mg/L, 5mg/L, 10mg/L, 20mg/L, 50mg/L and 100mg/L.
4. The quantitative test method according to claim 3, wherein the toluene concentration is 10mg/L to 100mg/L.
5. The quantitative test method of claim 1, wherein the result analysis further comprises:
calculating the polyester content in the sample to be detected based on a first formula, wherein the first formula is as follows:
wherein, c Polyester The content of polyester in the material, V is the volume of alcoholysis liquid, f is the dilution factor of the alcoholysis liquid during test, c i Measured concentration of dibasic acid dimethyl ester or hydroxy carboxylic acid methyl ester in alcoholysis solution, M i Is the relative molecular mass, M, of the dibasic acid dimethyl ester or the hydroxy carboxylic acid methyl ester in the alcoholysis solution i1 Is the relative molecular mass, M, of the dibasic acid or hydroxycarboxylic acid corresponding to the product in the alcoholysis solution i2 Is the relative molecular mass of dihydric alcohol in the polyester, n is the dehydration number in the polycondensation process, when the ester product in the alcoholysis solution is dibasic acid or dihydric alcohol polyester, n is 2 correspondingly, when the ester product in the alcoholysis solution is hydroxycarboxylic acid polyester, n is 1 water Is the relative molecular mass of water, m is the sample mass for the test procedure, and 10 is the conversion factor.
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Citations (3)
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| KR20110020539A (en) * | 2009-08-24 | 2011-03-03 | 주식회사 엘지화학 | Method for analyzing polyester-based resins |
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| KR20110020539A (en) * | 2009-08-24 | 2011-03-03 | 주식회사 엘지화학 | Method for analyzing polyester-based resins |
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| CN105334280A (en) * | 2015-10-16 | 2016-02-17 | 上海纺织集团检测标准有限公司 | Method used for qualitative and quantitative identification of PET, PTT, and PBT fiber, and compounds of PET, PTT, and PBT |
| CN114646703A (en) * | 2022-03-15 | 2022-06-21 | 湖北绿宇环保有限公司 | Method for testing content of diethylene glycol in flame-retardant polyester PET |
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