CN117623930A - Preparation method and application of toughening modifier for recycling polyethylene glycol terephthalate - Google Patents
Preparation method and application of toughening modifier for recycling polyethylene glycol terephthalate Download PDFInfo
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- CN117623930A CN117623930A CN202311728422.6A CN202311728422A CN117623930A CN 117623930 A CN117623930 A CN 117623930A CN 202311728422 A CN202311728422 A CN 202311728422A CN 117623930 A CN117623930 A CN 117623930A
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- polyethylene terephthalate
- recycled polyethylene
- recycling
- toughening modifier
- modifier
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- 239000003607 modifier Substances 0.000 title claims abstract description 38
- 238000004064 recycling Methods 0.000 title claims description 24
- 239000002202 Polyethylene glycol Substances 0.000 title claims description 11
- 229920001223 polyethylene glycol Polymers 0.000 title claims description 11
- KKEYFWRCBNTPAC-UHFFFAOYSA-L terephthalate(2-) Chemical compound [O-]C(=O)C1=CC=C(C([O-])=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-L 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 title claims description 9
- -1 polyethylene terephthalate Polymers 0.000 claims abstract description 59
- 229920000139 polyethylene terephthalate Polymers 0.000 claims abstract description 59
- 239000005020 polyethylene terephthalate Substances 0.000 claims abstract description 59
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims abstract description 28
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 19
- YGSDEFSMJLZEOE-UHFFFAOYSA-N salicylic acid Chemical compound OC(=O)C1=CC=CC=C1O YGSDEFSMJLZEOE-UHFFFAOYSA-N 0.000 claims abstract description 19
- 238000000034 method Methods 0.000 claims abstract description 17
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 claims abstract description 9
- 229960004889 salicylic acid Drugs 0.000 claims abstract description 9
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims description 16
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 10
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 8
- 238000001035 drying Methods 0.000 claims description 7
- 238000005406 washing Methods 0.000 claims description 6
- 238000003756 stirring Methods 0.000 claims description 5
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 4
- 230000007935 neutral effect Effects 0.000 claims description 3
- 238000002425 crystallisation Methods 0.000 abstract description 24
- 230000008025 crystallization Effects 0.000 abstract description 24
- 230000000694 effects Effects 0.000 abstract description 13
- 238000012545 processing Methods 0.000 abstract description 2
- 230000032050 esterification Effects 0.000 abstract 1
- 238000005886 esterification reaction Methods 0.000 abstract 1
- 238000006386 neutralization reaction Methods 0.000 abstract 1
- 238000002156 mixing Methods 0.000 description 19
- 230000000052 comparative effect Effects 0.000 description 16
- 238000001746 injection moulding Methods 0.000 description 13
- 235000013361 beverage Nutrition 0.000 description 11
- 239000000243 solution Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- 239000000463 material Substances 0.000 description 7
- 239000000203 mixture Substances 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
- 239000013078 crystal Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 2
- 239000002667 nucleating agent Substances 0.000 description 2
- 238000011084 recovery Methods 0.000 description 2
- 238000012795 verification Methods 0.000 description 2
- LLLVZDVNHNWSDS-UHFFFAOYSA-N 4-methylidene-3,5-dioxabicyclo[5.2.2]undeca-1(9),7,10-triene-2,6-dione Chemical compound C1(C2=CC=C(C(=O)OC(=C)O1)C=C2)=O LLLVZDVNHNWSDS-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 238000002347 injection Methods 0.000 description 1
- 239000007924 injection Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000002861 polymer material Substances 0.000 description 1
- 230000008707 rearrangement Effects 0.000 description 1
- 238000012958 reprocessing Methods 0.000 description 1
- 229920006126 semicrystalline polymer Polymers 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
Classifications
-
- 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
- Y02W30/00—Technologies for solid waste management
- Y02W30/50—Reuse, recycling or recovery technologies
- Y02W30/62—Plastics recycling; Rubber recycling
Landscapes
- Separation, Recovery Or Treatment Of Waste Materials Containing Plastics (AREA)
Abstract
Aiming at the characteristics of the recycled polyethylene terephthalate, the invention uses the reaction of esterification and neutralization of salicylic acid, terephthalic acid and lithium hydroxide to obtain the toughening modifier of the recycled polyethylene terephthalate. The modifier prepared by the invention can improve the tensile strength and crystallization temperature of the recycled polyethylene terephthalate through the effect of attached crystallization, has stable molecular structure, small addition amount and good effect in the processing process of the recycled polyethylene terephthalate, and has wide application prospect.
Description
Technical Field
The invention relates to a preparation method and application of a toughening modifier for recycling polyethylene glycol terephthalate, and belongs to the technical field of high polymer materials.
Background
Polyethylene terephthalate is a semi-crystalline polymer, and recycling and reprocessing the polymer is an important way to solve the problem of white pollution caused by plastic bottles. However, because the polyethylene terephthalate is subjected to a photo-thermal process in daily use, the toughness of the polyethylene terephthalate is reduced due to the breakage of a molecular chain, so that the difficulty in recycling is increased, and the requirement of high-performance products is also difficult to meet.
Therefore, improving the toughness of the recycled polyethylene terephthalate is an important problem in recycling the recycled polyethylene terephthalate, and development of a modifier for obtaining the recycled polyethylene terephthalate with good toughness by improving the crystallization property of the recycled polyethylene terephthalate is needed to solve the practical problem of the recycled polyethylene terephthalate and widen the application range of the modifier.
Disclosure of Invention
In order to solve the problems in the prior art, the invention provides a preparation method and application of a toughening modifier for recycling polyethylene terephthalate, and the toughness of the recycled polyethylene terephthalate is improved by improving the crystallization property of the recycled polyethylene terephthalate.
The invention provides a toughening modifier for recycling polyethylene glycol terephthalate, which is characterized by comprising the following molecular structures:
the preparation method of the toughening modifier for recycling polyethylene terephthalate is characterized by comprising the following steps of:
s1, dissolving 10 g salicylic acid and 4.6 g terephthalic acid in 200 mL dimethyl sulfoxide solution, adding 0.03 g concentrated sulfuric acid (98%), stirring 6 h at 100 ℃ by using an electric stirrer at 1000 rpm, washing the obtained solid by using 350 mL dimethyl sulfoxide solution after the reaction is finished, and drying at 80 ℃ until the weight is constant to obtain an intermediate A;
s2, placing 11.28 g intermediate A and 2 g lithium hydroxide into 200 mL deionized water, stirring at 80 ℃ by using an electric stirrer at 1000 rpm for 6 h, washing the obtained solid with ethanol and deionized water in sequence to be neutral, and drying at 80 ℃ to constant weight to obtain the toughening modifier for recycling polyethylene terephthalate.
Preferably, the dimethyl sulfoxide solution in the step S1 is used in an amount of 350 mL.
According to the invention, through verification, the too small dosage of the dimethyl sulfoxide solution in the step S1 can influence the pH value of the solution, so that the subsequent synthesis is difficult, and the excessive dosage can cause the waste of the solvent.
Preferably, the product in the step S2 is washed with ethanol and deionized water to obtain solid, and the solid is dried to constant weight at 80 ℃.
According to the invention, through verification, the unreacted impurities can be fully removed by sequentially washing with ethanol and deionized water, and in addition, the drying effect of the product cannot be ensured due to too high or too low drying temperature.
In addition, various reaction conditions and parameters in the preparation method of the toughening modifier for recycling polyethylene glycol terephthalate are better conditions verified by experiments.
The invention also provides a preparation method and application of the toughening modifier for recycling the polyethylene terephthalate, which are characterized in that the usage amount of the toughening modifier for recycling the polyethylene terephthalate is 0.5-1.5% of that of the recycled polyethylene terephthalate.
Preferably, the amount of the toughening modifier for recycling the polyethylene terephthalate is 1% of that of the recycled polyethylene terephthalate.
The addition of the toughening modifier of the recycled polyethylene glycol terephthalate synthesized by the invention is proper, so that the toughening effect can be better exerted, and the addition is a better condition verified by experiments.
Compared with the prior art, the invention has the following technical effects.
1. The molecular conjugated system of the modifier has lattice matching function in the crystallization process of the recycled polyethylene terephthalate, so that the recycled polyethylene terephthalate is easier to nucleate in the crystallization process and then initiate molecular chain rearrangement, thereby further improving the crystallization temperature and the crystallization rate of the recycled polyethylene terephthalate.
2. The microstructure of the modifier can induce the recycled polyethylene glycol terephthalate to generate attached crystals, so that the local crystal structure of the modifier is changed, and a good toughening effect is obtained.
3. The components of the nucleating agent are combined through chemical bonds, the molecular structure is stable, and the phenomenon that the effect of the modifying agent is lost or weakened due to decomposition can not be generated in the processing process of recycling polyethylene glycol terephthalate.
Detailed description of the preferred embodiments
In order to make the technical problems, technical solutions and advantageous effects to be solved by the present invention more apparent, the present invention will be further described in detail with reference to the following examples, and it should be understood that the specific examples described herein are only for explaining the present invention and are not intended to limit the present invention. Unless otherwise indicated, the materials, reagents and equipment used in the present invention are conventional and commercially available in the art.
Example 1
Dissolving 10 g salicylic acid (CAS: 69-72-7) and 4.6 g terephthalic acid (CAS: 100-21-0) in 200 mL dimethyl sulfoxide solution, adding 0.03 g concentrated sulfuric acid (98%) (CAS: 7664-93-9), stirring at 1000 rpm for 6 h at 100deg.C by using an electric stirrer, washing the obtained solid with 350 mL dimethyl sulfoxide solution after the reaction, and drying at 80deg.C to constant weight to obtain intermediate A;
11.28 g intermediate A and 2 g lithium hydroxide (CAS: 1310-65-2) are placed in 200 mL deionized water, stirred at 80 ℃ by an electric stirrer at 1000 rpm for 6 h, the obtained solid is washed with ethanol and deionized water in sequence to be neutral, and dried to constant weight at 80 ℃ to obtain the toughening modifier for recycling polyethylene terephthalate.
And (3) mixing the recycled polyethylene terephthalate (beverage bottle recycled material) with the toughening modifier in a high-speed mixer according to a mass ratio of 100:1 (mixing speed of 3000 rpm, mixing time of 5 min), extruding in a conventional double-screw extruder, granulating, and performing injection molding on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006, and the crystallization temperature (T cp ) Specific data are shown in table 1.
Example 2
This example is essentially the same as example 1, and a sample of a blend of recycled polyethylene terephthalate (beverage bottle regrind) was prepared and recycled polyethylene terephthalate (beverage bottle regrind) using the toughening modifier of recycled polyethylene terephthalate of this example in accordance with the method of example 1, and the mass ratio of recycled polyethylene terephthalate to the modifier synthesized in this example was 100:0.5, the tensile strength of the sample was measured according to the method described in GB/T1040-2006, the crystallization temperature (T cp ) Specific data are shown in table 1.
Example 3
This example is essentially the same as example 1, and a sample of a blend of recycled polyethylene terephthalate (beverage bottle regrind) was prepared and recycled polyethylene terephthalate (beverage bottle regrind) using the toughening modifier of recycled polyethylene terephthalate of this example in accordance with the method of example 1, and the mass ratio of recycled polyethylene terephthalate to the modifier synthesized in this example was 100:1.5, the tensile strength of the sample was measured according to the method described in GB/T1040-2006, the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 1
Pure recovery of the polymerThe ethylene terephthalate (beverage bottle recovery) was extruded in a conventional twin screw extruder, pelletized, and injection molded on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 2
And (3) mixing the recycled polyethylene terephthalate (beverage bottle recycled material) and the raw terephthalic acid in a high-speed mixer according to a mass ratio of 100:1 (mixing rotation speed of 3000 rpm, mixing time of 5 min), extruding in a conventional double-screw extruder, granulating, and performing injection molding on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 3
And (3) mixing the recycled polyethylene terephthalate (beverage bottle recycled material) and the raw material salicylic acid in a high-speed mixer according to a mass ratio of 100:1 (mixing rotation speed of 3000 rpm, mixing time of 5 min), extruding in a conventional double-screw extruder, granulating, and performing injection molding on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 4
And (3) mixing the recycled polyethylene terephthalate (beverage bottle recycled material) and the raw material lithium hydroxide in a high-speed mixer according to a mass ratio of 100:1 (mixing rotation speed of 3000 rpm, mixing time of 5 min), extruding in a conventional double-screw extruder, granulating, and performing injection molding on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 5
Raw materials are mixed10 After the salicylic acid g, the terephthalic acid 4.6 g and the lithium hydroxide 2 g are simply mixed in a high-speed mixer (the mixing rotating speed is 3000 rpm, the mixing time is 5 min), the salicylic acid g, the terephthalic acid 4.6 g and the lithium hydroxide 2 g are mixed with the recycled polyethylene terephthalate (the beverage bottle reclaimed material) in the high-speed mixer according to the mass ratio of 1:100 (the mixing rotating speed is 3000 rpm, the mixing time is 5 min), the mixture is extruded in a conventional double-screw extruder, and after granulation, the mixture is subjected to injection molding on an injection molding machine, a test sample is obtained. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Comparative example 6
And (3) mixing the recycled polyethylene terephthalate (beverage bottle recycled material) and the intermediate A in a high-speed mixer according to a mass ratio of 100:1 (mixing rotation speed of 3000 rpm, mixing time of 5 min), extruding in a conventional double-screw extruder, granulating, and performing injection molding on an injection molding machine to obtain a test sample. The tensile strength of the samples was determined according to the method described in GB/T1040-2006 standard and the crystallization temperature (T cp ) Specific data are shown in table 1.
Table 1 test results for each of examples and comparative examples
As can be seen from the experimental results of Table 1, the recovered polyethylene terephthalate with the modifier of the invention added in examples 1-3 has a higher tensile strength than the comparative example, and the crystallization temperature is also greatly improved compared with the comparative example, wherein example 1 with an addition of 1% is optimal. Compared with the pure recycled polyethylene terephthalate of the comparative example 1, the modifier synthesized by the invention has the effect of obviously improving the tensile strength and crystallization temperature of the recycled polyethylene terephthalate. In addition, too much or too little of the addition amount of the auxiliary agent adversely affects the tensile strength and crystallization temperature of the recycled polyethylene terephthalate.
The modifier prepared by the invention is combined through chemical reaction, so that the effect of improving the tensile strength and crystallization temperature of the recycled polyethylene terephthalate can be achieved. In contrast, comparative examples 2 to 5 were only single raw materials or conventional mixtures of raw materials, and did not undergo sufficient chemical reaction, and the above effects could not be fully exerted. Among them, terephthalic acid and salicylic acid added in comparative examples 2 and 3 can be used as heterogeneous nucleating agents to accelerate the crystallization rate of recovered polyethylene terephthalate, but have limited effects. In contrast, the molecular structure of the intermediate added in comparative example 6 can provide a substrate for the recycled polyethylene terephthalate with attached crystals, improving its crystallization rate and tensile strength, but there is a certain difference compared with example 1. Since the lithium hydroxide added in comparative example 4 is alkaline, it only plays a weak role in improving the tensile strength of the recycled polyethylene terephthalate. Comparative example 5, in which salicylic acid, terephthalic acid and lithium hydroxide were added, had only better lifting effect than comparative examples 2 to 4, in which a single component was added, since no chemical reaction occurred.
Therefore, the modifier for recycling the polyethylene terephthalate provided by the invention can play a beneficial role, so that the crystallization temperature and the tensile strength are improved, and the modifier has very important practical significance for widening the practical application scene of recycling the polyethylene terephthalate.
The foregoing description of the preferred embodiment of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, and alternatives falling within the spirit and principles of the invention.
Claims (5)
1. A preparation method and application of a toughening modifier for recycling polyethylene glycol terephthalate are characterized in that the molecular structure is shown in the following figure:
。
2. the method for preparing the toughening modifier for recycling polyethylene terephthalate and the application thereof according to claim 1, wherein the preparation method comprises the following steps:
s1, dissolving 10 g salicylic acid and 4.6 g terephthalic acid in 200 mL dimethyl sulfoxide solution, adding 0.03 g concentrated sulfuric acid (98%), stirring 6 h at 100 ℃ by using an electric stirrer at 1000 rpm, washing the obtained solid by using 350 mL dimethyl sulfoxide solution after the reaction is finished, and drying at 80 ℃ until the weight is constant to obtain an intermediate A;
s2, placing 11.28 g intermediate A and 2 g lithium hydroxide into 200 mL deionized water, stirring at 80 ℃ by using an electric stirrer at 1000 rpm for 6 h, washing the obtained solid with ethanol and deionized water in sequence to be neutral, and drying at 80 ℃ to constant weight to obtain the toughening modifier for recycling polyethylene terephthalate.
3. Use of a toughening modifier for recycling polyethylene terephthalate according to claim 1 or 2.
4. Use of a toughening modifier for recycled polyethylene terephthalate according to claim 3, in the recycling of polyethylene terephthalate, characterized in that: the dosage of the toughening modifier of the recycled polyethylene glycol terephthalate is 0.5-1.5% of the mass of the recycled polyethylene glycol terephthalate.
5. Use of a toughening modifier for recycled polyethylene terephthalate according to claim 3, in the recycling of polyethylene terephthalate, characterized in that: the dosage of the toughening modifier of the recycled polyethylene terephthalate is 1% of the mass of the recycled polyethylene terephthalate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311728422.6A CN117623930A (en) | 2023-12-15 | 2023-12-15 | Preparation method and application of toughening modifier for recycling polyethylene glycol terephthalate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202311728422.6A CN117623930A (en) | 2023-12-15 | 2023-12-15 | Preparation method and application of toughening modifier for recycling polyethylene glycol terephthalate |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CN117623930A true CN117623930A (en) | 2024-03-01 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CN202311728422.6A Pending CN117623930A (en) | 2023-12-15 | 2023-12-15 | Preparation method and application of toughening modifier for recycling polyethylene glycol terephthalate |
Country Status (1)
| Country | Link |
|---|---|
| CN (1) | CN117623930A (en) |
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2023
- 2023-12-15 CN CN202311728422.6A patent/CN117623930A/en active Pending
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