CN118005903A - Preparation method of polybutylene succinate with low extractables content - Google Patents
Preparation method of polybutylene succinate with low extractables content Download PDFInfo
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- CN118005903A CN118005903A CN202311843254.5A CN202311843254A CN118005903A CN 118005903 A CN118005903 A CN 118005903A CN 202311843254 A CN202311843254 A CN 202311843254A CN 118005903 A CN118005903 A CN 118005903A
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- polybutylene succinate
- succinate
- low extractables
- extractables content
- preparing
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- 229920002961 polybutylene succinate Polymers 0.000 title claims abstract description 112
- 239000004631 polybutylene succinate Substances 0.000 title claims abstract description 112
- -1 polybutylene succinate Polymers 0.000 title claims abstract description 83
- 239000012632 extractable Substances 0.000 title claims abstract description 42
- 238000002360 preparation method Methods 0.000 title claims abstract description 20
- 238000000034 method Methods 0.000 claims abstract description 31
- 239000002904 solvent Substances 0.000 claims abstract description 17
- 239000012456 homogeneous solution Substances 0.000 claims abstract description 14
- ZMKVBUOZONDYBW-UHFFFAOYSA-N 1,6-dioxecane-2,5-dione Chemical compound O=C1CCC(=O)OCCCCO1 ZMKVBUOZONDYBW-UHFFFAOYSA-N 0.000 claims abstract description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 26
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims description 24
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 239000007788 liquid Substances 0.000 claims description 19
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 16
- 238000005406 washing Methods 0.000 claims description 16
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 claims description 12
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 12
- 238000001035 drying Methods 0.000 claims description 10
- 238000001914 filtration Methods 0.000 claims description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 10
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 8
- 238000004090 dissolution Methods 0.000 claims description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 6
- BYEAHWXPCBROCE-UHFFFAOYSA-N 1,1,1,3,3,3-hexafluoropropan-2-ol Chemical compound FC(F)(F)C(O)C(F)(F)F BYEAHWXPCBROCE-UHFFFAOYSA-N 0.000 claims description 5
- 239000011259 mixed solution Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 claims 3
- 238000003756 stirring Methods 0.000 claims 1
- 229920000728 polyester Polymers 0.000 abstract description 3
- 239000012716 precipitator Substances 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 11
- 239000002244 precipitate Substances 0.000 description 9
- 239000002994 raw material Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 7
- 238000000746 purification Methods 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 4
- 125000004122 cyclic group Chemical group 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 238000009987 spinning Methods 0.000 description 3
- 230000008961 swelling Effects 0.000 description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000011031 large-scale manufacturing process Methods 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- 239000010936 titanium Substances 0.000 description 2
- 229910052719 titanium Inorganic materials 0.000 description 2
- NMPJHMFXHISVBR-UHFFFAOYSA-N 4-(oxolan-2-yloxy)butan-1-ol Chemical compound OCCCCOC1CCCO1 NMPJHMFXHISVBR-UHFFFAOYSA-N 0.000 description 1
- 241000221785 Erysiphales Species 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 229920003232 aliphatic polyester Polymers 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000007151 ring opening polymerisation reaction Methods 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/88—Post-polymerisation treatment
- C08G63/90—Purification; Drying
-
- 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
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W90/00—Enabling technologies or technologies with a potential or indirect contribution to greenhouse gas [GHG] emissions mitigation
- Y02W90/10—Bio-packaging, e.g. packing containers made from renewable resources or bio-plastics
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The application provides a preparation method of polybutylene succinate with low extractables content, belonging to the technical field of polyester preparation. Putting the polybutylene succinate slices into a good solvent to be dissolved to form a homogeneous solution system; adding a precipitator into the homogeneous solution system, and separating out the polybutylene succinate; the method provided by the application can effectively remove the oligomer component in the poly (butylene succinate) to obtain spinning-grade poly (butylene succinate) with low extractables content.
Description
Technical Field
The application relates to a preparation method of polybutylene succinate with low extractables content, belonging to the technical field of polyester preparation.
Background
Polybutylene succinate (PBS) is a biodegradable aliphatic polyester, and attracts more researchers and companies to research and produce because of its good ecological friendliness and applicability. PBS has similar mechanical properties to PE and PP, good flexibility, high elongation at break and excellent biodegradability, and can be used in the fields of packaging, disposable medical supplies, agricultural films, biomedical high polymer materials and the like.
PBS is generally synthesized from 1, 4-Butanediol (BDO) and succinic acid in a two-step process. In the first step, esterification reaction occurs to form oligomers. In the second step, the oligomers undergo transesterification and polycondensation to form PBS polymer. Due to the low forward reactivity of PBS, cyclic oligomers are easily produced during polymerization. The cyclic oligomer has a stable structure, and is difficult to undergo ring opening polymerization under high temperature conditions, and therefore, is likely to remain in PBS. PBS oligomer has great influence on the processing and forming process and the quality of products. For example, during the spinning process, oligomers tend to accumulate on the spinneret surface, affecting the smooth formation of the fiber. In the texturing link, the oligomer is easy to separate out from the fiber, and a large amount of powdery mildew is formed at the guide wire hook, so that the texturing is seriously affected. Therefore, efficient removal of oligomers in PBS is critical to improvement of its spinnability. However, few studies on spinning grade PBS are currently performed, and no work surrounding the removal of PBS oligomers and purification of PBS has been reported.
At present, the purification treatment of the high polymer is usually realized by three methods of vacuum devolatilization, swelling precipitation and dissolution precipitation. The vacuum devolatilization method is simple and convenient, but the oligomer is not completely removed; the swelling precipitation mode is difficult to control the removal ratio of the oligomer; the dissolution precipitation method is considered to be a relatively effective way of removing low molecular substances from a polymer.
In addition to the above purification methods, in some of the documents below, a bi-catalyst body formed by adding a specific inhibitor such as 4- [ (tetrahydro-2-furanyl) oxy ] -1-butanol, a liquid-phase titanium-based composite catalyst and a metal compound catalyst or a titanium silicalite molecular sieve catalyst supporting an ionic liquid, or the reaction temperature is controlled to a lower level such as 80 to 130 ℃. However, the problems of high energy consumption, high cost, easy introduction of foreign matters and the like are caused. At present, purification around PBS has yet to be studied.
Disclosure of Invention
In view of the above, the application provides a preparation method of low-extractables content poly (butylene succinate), which can effectively remove oligomer components in poly (butylene succinate) to obtain spinning-grade poly (butylene succinate) with the extractables content less than or equal to 0.8%.
Specifically, the application is realized by the following scheme:
a preparation method of polybutylene succinate with low extractables content comprises the following steps:
Step one, putting the polybutylene succinate slices into a good solvent, and thoroughly dissolving at a certain temperature to form a homogeneous solution system.
And step two, adding a certain amount of precipitant to separate the polybutylene succinate from the solution, and separating the polybutylene succinate from the clear liquid.
And thirdly, repeatedly washing the precipitate with a specific solvent, filtering and drying until the constant weight is maintained, and finally obtaining the spinning-grade polybutylene succinate with low extractable matter content.
Aiming at the problems of high extractable matter content, difficult spinning and post-treatment and poor product performance of the prior PBS, the solution degree of the PBS in solvents with different polarities is utilized in the scheme, the PBS is firstly formed into a homogeneous solution system by adopting a good solvent, and then the solution system is separated out by utilizing a precipitant, so that the extraction of the oligomer in the PBS is completed. The method is simple and convenient to operate, can be realized by a simple treatment process, and is convenient for large-scale production.
Further, as preferable:
In the first step:
the good solvent includes but is not limited to hexafluoroisopropanol, phenol/tetrachloroethane, chloroform, methylene chloride. The PBS is dissolved by utilizing different dissolution degrees of the PBS in solvents with different polarities, and the good solvent selected in the scheme is a solvent with smaller polarity, so that the molecular weight of the dissolved polymer is lower. More preferably, the volume ratio of the phenol/tetrachloroethane mixed solution is 1:1.
The solid-liquid ratio of the poly (butylene succinate) to the good solvent is 1:15-20 (the ratio of the mass of the poly (butylene succinate) to the volume of the good solvent).
The dissolution temperature is controlled to be 30-55 ℃.
In the second step:
The precipitants include, but are not limited to, water, ethanol, acetone, cyclohexane, tetrahydrofuran.
The addition amount of the precipitant is 30-60 times of the mass of the polybutylene succinate raw material.
In the third step:
Solvents used for the washing include, but are not limited to, water, ethanol, acetone, cyclohexane, tetrahydrofuran; the washing refers to a cyclic process of "dispersion-agitation washing-filtration-redispersion".
Compared with the existing PBS slicing and purifying method, the preparation process has the following beneficial effects:
1) Compared with the common purification methods in the polyester field, such as hexafluoroisopropanol dissolution, tetrahydrofuran precipitation and other schemes, the method provided by the invention can expand the PBS oligomer removal range from the polymerization degree of 1-3 to 1-10.
2) The content of PBS extractables commonly used in the market is generally higher than 3%, and the content of the polybutylene succinate extractables prepared by the method is less than or equal to 0.8%.
3) The extractables content in the existing conventional polymer purification process such as vacuum devolatilization and swelling precipitation treatment of polymer slices, such as water washing purification of polyamide 6, is still higher than 2%. The method provided by the invention can be used for treating PBS, so that the content of extractables of PBS can be effectively reduced, and the spinning-grade PBS with low content of extractables and high purity can be obtained.
According to the technical scheme, through three steps of PBS dissolution, precipitation and washing, PBS slices are dissolved in a good solvent with smaller polarity, and then a poor solvent with larger polarity is added to precipitate PBS, so that oligomers in the PBS are extracted, the problems of high content of extractables of polybutylene succinate, difficult processing and poor product performance in the prior art are effectively solved, and the preparation of the low-extractables and high-purity spinning-grade PBS can be realized through a simple treatment process by a conventional device, so that the preparation method is convenient for large-scale production.
Detailed Description
Example 1
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into dichloromethane, and thoroughly dissolving at 40 ℃ to form a homogeneous solution system; separating out the polybutylene succinate from the solution by adding tetrahydrofuran, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with ethanol, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.08%.
Wherein, the solid-to-liquid ratio of the polybutylene succinate to the methylene dichloride is 1:20; the adding amount of tetrahydrofuran is 30 times of the mass of the polybutylene succinate raw material.
Example 2
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into a mixed solvent of phenol/tetrachloroethane according to a ratio of 1:1, and thoroughly dissolving at 30 ℃ to form a homogeneous solution system; separating out the polybutylene succinate from the solution by adding ethanol, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with tetrahydrofuran, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.05%.
Wherein the solid-to-liquid ratio of the polybutylene succinate to the mixed solvent of phenol/tetrachloroethane is 1:20; the addition amount of the ethanol is 40 times of the mass of the polybutylene succinate raw material.
Example 3
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
putting the polybutylene succinate slices into hexafluoroisopropanol, and thoroughly dissolving at 50 ℃ to form a homogeneous solution system; adding acetone to separate out the polybutylene succinate from the solution, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with water, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.25%.
Wherein the solid-to-liquid ratio of the polybutylene succinate to the acetone is 1:15; the addition amount of the acetone is 40 times of the mass of the polybutylene succinate raw material.
Example 4
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into hexafluoroisopropanol, and thoroughly dissolving at 30 ℃ to form a homogeneous solution system; separating out the polybutylene succinate from the solution by adding tetrahydrofuran, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with ethanol, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.3%.
Wherein, the solid-to-liquid ratio of the polybutylene succinate to the tetrahydrofuran is 1:15; the adding amount of tetrahydrofuran is 40 times of the mass of the polybutylene succinate raw material.
Example 5
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into chloroform, and thoroughly dissolving at 55 ℃ to form a homogeneous solution system; separating out the polybutylene succinate from the solution by adding cyclohexane, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with acetone, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.02%.
Wherein, the solid-to-liquid ratio of the polybutylene succinate to the cyclohexane is 1:15; the addition amount of the acetone is 30 times of the mass of the polybutylene succinate raw material.
Example 6
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into dichloromethane, and thoroughly dissolving at 40 ℃ to form a homogeneous solution system; adding water to separate out the polybutylene succinate from the solution, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with acetone, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.8%.
Wherein the solid-to-liquid ratio of the polybutylene succinate to the water is 1:20; the addition amount of the acetone is 60 times of the mass of the polybutylene succinate raw material.
Example 7
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
putting the polybutylene succinate slices into dichloromethane, and thoroughly dissolving at 45 ℃ to form a homogeneous solution system; separating out the polybutylene succinate from the solution by adding tetrahydrofuran, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with cyclohexane, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.08%.
Wherein, the solid-to-liquid ratio of the polybutylene succinate to the methylene dichloride is 1:17; the adding amount of cyclohexane is 40 times of the mass of the polybutylene succinate raw material.
Example 8
The preparation process of the polybutylene succinate with low extractables content in the embodiment is as follows:
Putting the polybutylene succinate slices into dichloromethane, and thoroughly dissolving at 35 ℃ to form a homogeneous solution system; adding acetone to separate out the polybutylene succinate from the solution, and separating the polybutylene succinate from the clear liquid; repeatedly washing the precipitate with water, filtering, and drying to constant weight to obtain spinning-grade polybutylene succinate with the extractable matter content of 0.7%.
Wherein, the solid-liquid ratio of the poly butylene succinate to the acetone is 1:20; the water addition amount is 60 times of the mass of the polybutylene succinate raw material.
Claims (9)
1. A preparation method of polybutylene succinate with low extractables content is characterized by comprising the following steps:
step one, putting a polybutylene succinate slice into a good solvent to be dissolved to form a homogeneous solution system;
step two, adding a precipitant into the homogeneous solution system to separate out and separate out the polybutylene succinate;
And thirdly, washing the separated poly (butylene succinate), filtering and drying to constant weight to obtain the poly (butylene succinate) with the extract content less than or equal to 0.8%.
2. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: the good solvent is one or a mixture of more of hexafluoroisopropanol, phenol/tetrachloroethane, chloroform and methylene dichloride.
3. The method for preparing the polybutylene succinate with low extractables content according to claim 2, wherein the method comprises the following steps: the volume ratio of the phenol/tetrachloroethane mixed solution is 1:1.
4. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: the solid-liquid ratio of the poly (butylene succinate) slice to the good solvent is 1:15-20.
5. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: the dissolution temperature is 30-55 ℃.
6. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: the precipitant is any one or a mixture of more of water, ethanol, acetone, cyclohexane and tetrahydrofuran.
7. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: the addition amount of the precipitant is 30-60 times of the slice mass of the polybutylene succinate.
8. The method for preparing the polybutylene succinate with low extractables content according to claim 1, wherein the method comprises the following steps: in the third step, any one or a mixture of more of water, ethanol, acetone, cyclohexane and tetrahydrofuran is adopted for washing.
9. The method for preparing polybutylene succinate with low extractables content according to claim 1, wherein in the third step, the washing means: the cycle of dispersing-stirring washing-filtering-redispersing.
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311843254.5A CN118005903A (en) | 2023-12-29 | 2023-12-29 | Preparation method of polybutylene succinate with low extractables content |
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| Application Number | Priority Date | Filing Date | Title |
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| CN202311843254.5A CN118005903A (en) | 2023-12-29 | 2023-12-29 | Preparation method of polybutylene succinate with low extractables content |
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| CN118005903A true CN118005903A (en) | 2024-05-10 |
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