CN116063666B - Multifunctional polyester material and preparation method and application thereof - Google Patents
Multifunctional polyester material and preparation method and application thereof Download PDFInfo
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- CN116063666B CN116063666B CN202111289897.0A CN202111289897A CN116063666B CN 116063666 B CN116063666 B CN 116063666B CN 202111289897 A CN202111289897 A CN 202111289897A CN 116063666 B CN116063666 B CN 116063666B
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- 229920000728 polyester Polymers 0.000 title claims abstract description 57
- 239000000463 material Substances 0.000 title claims abstract description 50
- 238000002360 preparation method Methods 0.000 title claims abstract description 16
- 125000003118 aryl group Chemical group 0.000 claims description 31
- -1 phenylacetyl Chemical group 0.000 claims description 29
- 239000000178 monomer Substances 0.000 claims description 23
- 125000000217 alkyl group Chemical group 0.000 claims description 15
- 125000001072 heteroaryl group Chemical group 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 150000002009 diols Chemical class 0.000 claims description 13
- 238000003756 stirring Methods 0.000 claims description 12
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 11
- 238000010438 heat treatment Methods 0.000 claims description 11
- 230000002209 hydrophobic effect Effects 0.000 claims description 10
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 230000009194 climbing Effects 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 238000004519 manufacturing process Methods 0.000 claims description 4
- 239000000203 mixture Substances 0.000 claims description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims description 4
- 238000012216 screening Methods 0.000 claims description 3
- 125000003107 substituted aryl group Chemical group 0.000 claims description 3
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Divinylene sulfide Natural products C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 claims description 2
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 2
- 239000004305 biphenyl Substances 0.000 claims description 2
- 235000010290 biphenyl Nutrition 0.000 claims description 2
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 125000006332 fluoro benzoyl group Chemical group 0.000 claims description 2
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 2
- 125000003104 hexanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000011261 inert gas Substances 0.000 claims description 2
- 125000001038 naphthoyl group Chemical group C1(=CC=CC2=CC=CC=C12)C(=O)* 0.000 claims description 2
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 2
- 238000004321 preservation Methods 0.000 claims description 2
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 2
- 229930192474 thiophene Natural products 0.000 claims description 2
- 125000003774 valeryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000002431 hydrogen Chemical group 0.000 claims 4
- 150000001408 amides Chemical class 0.000 claims 2
- 150000002148 esters Chemical class 0.000 claims 2
- 239000004890 Hydrophobing Agent Substances 0.000 claims 1
- 238000009472 formulation Methods 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 abstract description 3
- 238000003786 synthesis reaction Methods 0.000 abstract description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 24
- 238000012360 testing method Methods 0.000 description 23
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 12
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 12
- 229910052757 nitrogen Inorganic materials 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 12
- DTQVDTLACAAQTR-UHFFFAOYSA-N Trifluoroacetic acid Chemical compound OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 10
- 239000003054 catalyst Substances 0.000 description 8
- 239000002861 polymer material Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical group [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 6
- 239000004246 zinc acetate Substances 0.000 description 6
- 238000010521 absorption reaction Methods 0.000 description 5
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 4
- 230000015556 catabolic process Effects 0.000 description 4
- 238000006731 degradation reaction Methods 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 238000001556 precipitation Methods 0.000 description 4
- 238000005086 pumping Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000012265 solid product Substances 0.000 description 4
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 230000008901 benefit Effects 0.000 description 3
- 238000009826 distribution Methods 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 description 2
- 125000003368 amide group Chemical group 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 230000008859 change Effects 0.000 description 2
- 239000002537 cosmetic Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 125000004185 ester group Chemical group 0.000 description 2
- 239000010408 film Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 230000003993 interaction Effects 0.000 description 2
- 239000011572 manganese Substances 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 230000010287 polarization Effects 0.000 description 2
- 230000008569 process Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 230000008439 repair process Effects 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000001291 vacuum drying Methods 0.000 description 2
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- WBYWAXJHAXSJNI-SREVYHEPSA-N Cinnamic acid Chemical compound OC(=O)\C=C/C1=CC=CC=C1 WBYWAXJHAXSJNI-SREVYHEPSA-N 0.000 description 1
- 239000004243 E-number Substances 0.000 description 1
- 235000019227 E-number Nutrition 0.000 description 1
- YBGZDTIWKVFICR-JLHYYAGUSA-N Octyl 4-methoxycinnamic acid Chemical compound CCCCC(CC)COC(=O)\C=C\C1=CC=C(OC)C=C1 YBGZDTIWKVFICR-JLHYYAGUSA-N 0.000 description 1
- 239000004793 Polystyrene Substances 0.000 description 1
- 238000005147 X-ray Weissenberg Methods 0.000 description 1
- 239000004480 active ingredient Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- WSXIMVDZMNWNRF-UHFFFAOYSA-N antimony;ethane-1,2-diol Chemical compound [Sb].OCCO WSXIMVDZMNWNRF-UHFFFAOYSA-N 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 229930016911 cinnamic acid Natural products 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- 229940011182 cobalt acetate Drugs 0.000 description 1
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 1
- 239000012612 commercial material Substances 0.000 description 1
- 208000012839 conversion disease Diseases 0.000 description 1
- 230000007547 defect Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- HJUFTIJOISQSKQ-UHFFFAOYSA-N fenoxycarb Chemical compound C1=CC(OCCNC(=O)OCC)=CC=C1OC1=CC=CC=C1 HJUFTIJOISQSKQ-UHFFFAOYSA-N 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000005431 greenhouse gas Substances 0.000 description 1
- 238000005286 illumination Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 239000002121 nanofiber Substances 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 229960001679 octinoxate Drugs 0.000 description 1
- 239000008055 phosphate buffer solution Substances 0.000 description 1
- 238000006068 polycondensation reaction Methods 0.000 description 1
- 229920002223 polystyrene Polymers 0.000 description 1
- 239000012716 precipitator Substances 0.000 description 1
- 230000002035 prolonged effect Effects 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000009864 tensile test Methods 0.000 description 1
- 238000009210 therapy by ultrasound Methods 0.000 description 1
- 230000000930 thermomechanical effect Effects 0.000 description 1
- 239000010409 thin film Substances 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 239000011787 zinc oxide Substances 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
- C08G63/02—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
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/19—Hydroxy compounds containing aromatic rings
- C08G63/193—Hydroxy compounds containing aromatic rings containing two or more aromatic rings
-
- 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
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
- C08G63/185—Acids containing aromatic rings containing two or more aromatic rings
-
- 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
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/682—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens
- C08G63/6824—Polyesters containing atoms other than carbon, hydrogen and oxygen containing halogens derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6826—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
-
- 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
- C08G63/78—Preparation processes
-
- 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
- C08G2230/00—Compositions for preparing biodegradable polymers
-
- 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
- Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
- Y02P20/00—Technologies relating to chemical industry
- Y02P20/50—Improvements relating to the production of bulk chemicals
- Y02P20/54—Improvements relating to the production of bulk chemicals using solvents, e.g. supercritical solvents or ionic liquids
Abstract
The invention discloses a multifunctional polyester material, a preparation method and application thereof, and belongs to the technical field of polyester materials and synthesis thereof.
Description
Technical Field
The invention relates to the technical field of polyester materials and synthesis thereof, in particular to a multifunctional polyester material and a preparation method and application thereof.
Background
The ongoing development of the modern industry has resulted in substantial emissions of CO 2, whereas CO 2, as a greenhouse gas, directly or indirectly results in global warming. Therefore, the development of emission reduction and utilization of the corresponding CO 2 is significant. How to change low-value CO 2 into a product with high added value is always the direction of the endeavor pursuit of the scientific community. However, the effective utilization of CO 2, especially in terms of industrialization, is often not satisfactory. The reason for this is that CO 2 has kinetic inert and thermodynamic stability characteristics.
The polymer material plays an important role in our daily life and production process as one of three branches in the material field. However, the production of the traditional high polymer material is seriously dependent on petrochemical raw materials, which is very unfavorable for China relying on petroleum import, and the petroleum-based high polymer material is difficult to recover and degrade after the service life is finished. Therefore, the development of a series of polymer materials with green sources has important significance. If the dimethyl ester monomer derived from CO 2 can be used as a monomer source in the field of high polymer materials, the high additional value utilization of CO 2 can be realized, and a new idea can be provided for the green development in the field of high polymer materials. Meanwhile, the degradable material can effectively reduce white pollution, and has important significance for developing environment-friendly materials.
At present, a series of CO 2 -based degradable multifunctional polyester materials prepared by taking CO 2 -based dimethyl glutarate as a high polymer material monomer are not reported.
Disclosure of Invention
Aiming at the defects, the invention aims to provide a multifunctional polyester material and a preparation method and application thereof. According to the invention, the CO 2 dimethyl glutarate compound is used as a high molecular material monomer to carry out melt polymerization with a functional diol monomer, so that a series of multifunctional degradable polyester materials with excellent self-repairing, ultraviolet shielding and hydrophobic performances on the CO 2 base are prepared.
In order to achieve the above purpose, the invention adopts the following technical scheme:
the invention provides a multifunctional polyester material, which comprises the following repeated structural units:
Wherein R 1 is aryl, aryl substituted with one or more R 1a, or electron withdrawing group; r 2 is hydrogen, alkyl or alkyl substituted with one or more R 1a; r 3 is aryl, aryl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, or electron withdrawing group; r 4 is hydrogen, alkyl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, aryl, or aryl substituted with one or more R 1a; r 5 is at least one of substituted aryl, heteroaryl, and alkyl; r 6 is formyl, acetyl, butyryl, pentanoyl, hexanoyl, propionyl, benzoyl, phenylacetyl, phenylpropionyl, phenylbutyryl, phenylpentanoyl, phenylhexanoyl, bromobenzoyl, chlorobenzoyl, fluorobenzoyl, trifluoromethylbenzoyl, naphthoyl, biphenyl acyl, methylbenzoyl, pyridine acyl, thiophene acyl or furan acyl; r 7、R8 and R 9 are each aryl, aryl substituted with one or more R 1a, heteroaryl, or heteroaryl substituted with one or more R 1a; r 1a is C 1～C10 alkyl, halogen, ester group, cyano or amide group, etc.; the polymerization degrees a, b and c are natural numbers in the range of 2 to 130.
Further, the preferred structural formula of the above aryl group is as follows:
further, the preferred structural formula of the electron withdrawing group is as follows:
The invention also provides a preparation method of the multifunctional polyester material, which comprises the following steps: adding a CO 2 -yl dimethyl glutarate compound and a functional diol monomer into a reaction device, continuously stirring under the protection of inert gas, heating to melt, and carrying out heat preservation reaction for 3-12 h; then heating to 200-240 ℃, reacting for 0.5-3 h under the vacuum degree of 450-500 Pa, continuing to react under the vacuum degree of 40-50 Pa until the pole climbing phenomenon occurs, and separating and purifying to obtain the multifunctional polyester material;
Wherein, the mol ratio of the CO 2 dimethyl glutarate compound to the functional diol monomer is 1:1-3;
the structural general formula of the CO 2 -yl dimethyl glutarate compound is shown as follows:
Wherein R 1 is aryl, aryl substituted with one or more R 1a, or electron withdrawing group; r 2 is hydrogen, alkyl or alkyl substituted with one or more R 1a; r 3 is aryl, aryl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, or electron withdrawing group; r 4 is hydrogen, alkyl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, aryl, or aryl substituted with one or more R 1a; r 5 is at least one of substituted aryl, heteroaryl, and alkyl; r 1a is C 1～C10 alkyl, halogen, ester group, cyano or amide group, etc.
The pole climbing phenomenon is referred to as Weissenberg effect (normal stress effect) of the polymer melt, and is also referred to as a wraparound phenomenon.
Further, the preferred structural formula of the above aryl group is as follows:
further, the preferred structural formula of the electron withdrawing group is as follows:
further, the molar ratio of the CO 2 dimethyl glutarate compound to the functional diol monomer is 1:1-1.6.
Further, the structural formula of the functional diol monomer is shown as follows:
further, the melting temperature is preferably 170 to 190 ℃.
Further, the temperature is raised to melt, and the reaction time is preferably 5 to 8 hours, more preferably 6 hours.
Further, the specific process of separation and purification is as follows: completely dissolving a product obtained by the reaction in a solvent to obtain a product solution; then dripping the mixture into a precipitator with the volume 5 to 7 times of that of the product solution, stirring to obtain a powdery product, filtering the powdery product, and drying the powdery product in a vacuum drying oven at the temperature of between 40 and 60 ℃ for 12 to 48 hours.
Further, the solvent of the dissolved product is selected from mixed solvent or chloroform composed of chloroform/trifluoroacetic acid with the volume ratio of 4-6:1-2.
Further, the precipitant is methanol, acetone or diethyl ether.
Further, in order to accelerate the reaction rate, the invention also comprises a catalyst in the reaction system, wherein the catalyst is zinc acetate/antimonous oxide, tetrabutyl titanate, manganese acetate, cobalt acetate or ethylene glycol antimony. Preferably zinc acetate/antimony trioxide or tetrabutyl titanate; wherein the dosage of the catalyst is 0.1 to 0.5 weight percent of the total mass of the reaction monomers.
The invention also provides application of the multifunctional polyester material in preparing an ultraviolet shielding agent and/or a hydrophobic agent and/or a self-repairing preparation.
A self-repairing agent adopts the multifunctional polyester material as a main component.
An ultraviolet shielding preparation adopts the multifunctional polyester material as a main component.
A hydrophobic preparation comprises the multifunctional polyester material as main ingredient.
In summary, the invention has the following advantages:
1. The invention provides a multifunctional polyester material, which is prepared by using a CO 2 dimethyl glutarate compound as a high polymer material monomer to carry out melt polymerization with a functional diol monomer, introducing a plurality of benzene ring structures into a main chain and a side chain of the multifunctional polyester material, so that pi-pi interaction occurs between molecular chains of the polyester material, and simultaneously, the pi-pi interaction is further enhanced along with mutual entanglement of chain segments, thereby realizing the function of self-repairing when the polyester material is subjected to external physical damage; the invention also introduces the diaryl ketone structure and a plurality of fluorine atom substituents into the polyester chain segment structure at the same time, thereby realizing the effective shielding of the polyester material on ultraviolet and excellent hydrophobic performance, and finally preparing a series of multifunctional degradable polyester materials with excellent self-repairing, ultraviolet shielding and hydrophobic performance on CO 2 groups.
2. The invention provides a method for green synthesis of polyester, which is derived from a raw material monomer-CO 2 -yl dimethyl glutarate compound serving as carbon dioxide and has important significance for realizing 'carbon reaching peak' and 'carbon neutralization' targets in China. Meanwhile, the preparation method has the characteristics of simplicity, easiness in operation, high efficiency and high yield.
Drawings
FIG. 1 is a self-healing diagram of a polyester material of the present invention;
FIG. 2 is a graph showing the results of a self-healing tensile test of a polyester material of the present invention;
FIG. 3 is a graph showing the ultraviolet absorption curve of the polyester material of the present invention;
FIG. 4 is a graph showing the water contact angle test results of the polyester material of the present invention;
FIG. 5 shows GPC test results of polyester materials of the present invention.
Detailed Description
The present invention will be described in further detail with reference to the following examples in order to make the objects, technical solutions and advantages of the present invention more apparent. It should be understood that the particular embodiments described herein are illustrative only and are not intended to limit the invention, i.e., the embodiments described are merely some, but not all, of the embodiments of the invention.
Thus, the following detailed description of the embodiments of the invention, as provided, is not intended to limit the scope of the invention, as claimed, but is merely representative of selected embodiments of the invention. All other embodiments, which can be made by a person skilled in the art without making any inventive effort, are intended to be within the scope of the present invention.
The preferred embodiments of the present invention are illustrated below.
Example 1
In order to obtain higher reaction conversion and polymer molecular weight, the polymerization conditions were subjected to condition screening using diol monomer-compound a and diacid monomer-compound B as reaction monomers in this example, and the specific results are shown in table 1 below.
TABLE 1
Note that: reaction conditions: diacid monomer (15 mmol), diol monomer (15 mmol), zinc acetate (0.2 wt%), antimony trioxide (0.3 wt%), prepolymerization time: 12h, polycondensation time: 12h; a, catalyst tetrabutyl titanate; and b, prepolymerizing for 6h. c, prepolymerizing for 18h; d, e number average molecular weight and molecular weight distribution were determined by GPC.
Example 2
The reaction formula of this example is as follows:
In a 50mL polymerization flask equipped with a nitrogen inlet and outlet and a mechanical stirrer, glycol (15 mmol) and dimethyl ester (15 mmol) monomers, zinc acetate (0.2 wt%) and antimony trioxide (0.3 wt%) were added as catalysts; placing the polymerization bottle on a double-row pipe, pumping and replacing nitrogen for three times, heating to 190 ℃ under the protection of nitrogen, and stirring for about 12 hours under the condition; then the temperature is increased to 240 ℃, and the mixture is stirred for 0.5 to 1 hour under the vacuum degree with the pressure of about 500 Pa; stirring is continued under the vacuum degree with the pressure of 50Pa until the pole climbing phenomenon appears. The solid product obtained was dissolved in 50mL of a chloroform/trifluoroacetic acid (volume ratio: 5:1) mixed solvent, and then the solution was added dropwise to 100mL of glacial methanol for precipitation, and the solid was filtered to obtain pale yellow powder. And then dried in a vacuum oven at 60 ℃ for 24 hours. The specific results are as follows:
Wherein the structure of PBH-1 is characterized as follows ：1H NMR(400MHz,DMSO-d6)δ7.65–7.00(m,18H),3.95(br,8H),3.60–3.44(m,8H),1.75–1.19(m,16H);13C NMR(101MHz,DMSO-d6)δ193.09,172.57,172.54,172.49,161.93,138.21,138.14,129.86,127.75,127.44,114.10,67.65,67.03,64.30,48.87,48.57,36.02,28.38,27.87,25.14,24.96.
Example 3
The reaction formula of this example is as follows:
In a 50mL polymerization flask equipped with a nitrogen inlet and outlet and a mechanical stirrer, glycol (15 mmol) and dimethyl ester (15 mmol) monomers, zinc acetate (0.2 wt%) and antimony trioxide (0.3 wt%) were added as catalysts; placing the polymerization bottle on a double-row pipe, pumping and replacing nitrogen for three times, heating to 190 ℃ under the protection of nitrogen, and stirring for about 12 hours under the condition; then the temperature is increased to 240 ℃, and the mixture is stirred for 0.5 to 1 hour under the vacuum degree with the pressure of about 500 Pa; stirring is continued under the vacuum degree with the pressure of 50Pa until the pole climbing phenomenon appears. The solid product obtained was dissolved in 15mL of a chloroform/trifluoroacetic acid (volume ratio: 5:1) mixed solvent, and then the solution was added dropwise to 100mL of glacial methanol for precipitation, and the solid was filtered to obtain pale yellow powder. And then dried in a vacuum oven at 60 ℃ for 24 hours. The specific results are as follows:
Example 4
The reaction equation of this example is as follows:
In a 50mL polymerization flask equipped with a nitrogen inlet and outlet and a mechanical stirrer, diol (1.1025 g) and dimethyl ester (1.2495 g) monomers and tetrabutyl titanate (8. Mu.L) were added as catalysts; placing the polymerization bottle on a double-row pipe, pumping and replacing nitrogen for three times, heating to 190 ℃ under the protection of nitrogen, and stirring for about 12 hours under the condition; then the temperature is increased to 230 ℃ and stirred for 2 hours under the vacuum degree with the pressure of about 500 Pa; stirring is continued under the vacuum degree with the pressure of 50Pa until the pole climbing phenomenon appears. The solid product obtained was dissolved in 15mL of a chloroform/trifluoroacetic acid (volume ratio: 5:1) mixed solvent, and then the solution was added dropwise to 100mL of glacial methanol for precipitation, and the solid was filtered to obtain pale yellow powder. And then dried in a vacuum oven at 60 ℃ for 24 hours. M n＝29700,Mw/Mn＝1.39,T5％＝346℃,Tg = 75 ℃ of the resulting polyester.
Example 5
The reaction equation of this example is as follows:
In a 50mL polymerization flask equipped with a nitrogen inlet and outlet and a mechanical stirrer, glycol (0.2122 g) and dimethyl ester (0.9371 g) monomers, zinc acetate (2.3 mg) and antimony trioxide (3.5 mg) were added as catalysts; placing the polymerization bottle on a double-row pipe, pumping and replacing nitrogen for three times, heating to 190 ℃ under the protection of nitrogen, and stirring for 12 hours under the condition; then the temperature is increased to 240 ℃ and stirred for 2 hours under the vacuum degree with the pressure of 500 Pa; continuously stirring under the vacuum degree with the pressure of 50Pa until the pole climbing phenomenon occurs; the obtained solid product is dissolved by 15mL of mixed solvent of chloroform/trifluoroacetic acid (volume ratio is 5:1), then the solution is dripped into 100mL of glacial methanol for precipitation, and the solid is filtered to obtain light yellow powder; drying in a vacuum drying oven at 60 ℃ for 24 hours; m n＝43500,Mw/Mn = 1.64 of the resulting polyester.
Examples
In order to examine the properties of the polyesters obtained according to the invention in terms of self-repair, UV-shielding and hydrophobicity. Some of the polyesters obtained in examples 1 to 3 were now subjected to self-healing, UV shielding and hydrophobic testing.
The test instrument and instrument use procedure were as follows:
Gel chromatograph (GPC): the polymer molecular weight and its distribution were measured by gel permeation chromatograph model 2414 from Waters company, and the sample was dissolved in chromatographically pure tetrahydrofuran at a concentration of about 5mg/mL. Polystyrene was used as a standard, tetrahydrofuran was used as the mobile phase, the flow rate was 1.0mL/Min, and the test temperature was 30 ℃.
Dynamic thermo-mechanical test (DMA): the test was performed on a DMA242C analyzer manufactured by the german relaxation company. The stretching mode is selected, the experimental temperature is from room temperature to 60 ℃, the heating rate is 5 ℃/min, and the testing frequency is 1Hz.
Ultraviolet visible absorption (UV-Vis): in the preparation process, firstly, a sample to be tested is prepared into a DMF solution of 0.1mg/mL, then ultrasonic treatment is carried out for 5min, after the sample is uniformly dispersed, the suspension is poured into a quartz cuvette, and finally, instrument parameters are adjusted, wherein the wavelength range is 200-800nm.
Hot stage polarization microscope (POM): the self-repairing process of the PBH-1 thin film was observed using a polarization microscope of ECLIPSE LV POL (transmission/epi-illumination) in Japanese.
Mechanical strength test: the tensile strength and the elongation at break of the polyester are tested according to national standard GB1040-2006, a miniature injection molding machine which is newly filled in Shanghai is adopted to prepare the polyester according to a 1BA type spline in the national standard, the tensile strength and the elongation at break are tested on a universal mechanical machine, and the tensile rate is 10mm/min.
Contact angle test (WCA): the static contact angle of the test sample was measured using DCAT meter/interface tensiometer from delfei, germany, using water as the test liquid.
The resulting polyester materials were found to contain multiple benzene ring structures in the backbone structure,
Self-repair test
The self-repairing test polyester has the following structure:
First, a dumbbell bar (35 mm x 5mm x 0.5 mm) was cut into two sections from the middle. And then spliced together. Then put into an oven for repair for 5 hours at 50 ℃. During which no external force is applied. The self-repairing sample can bear a weight of 250 times its own weight without breaking (fig. 1a and 1 c). To further confirm the self-healing ability of the material, scratches were made on the film surface with a blade, and then the samples were placed on a heated table at 50 ℃ and the change in scratches was detected with POM (fig. 1 b). It can be seen that the scratches on the film gradually become narrower as the heating time is prolonged, and eventually the scratches disappear after heating for 90 minutes. The self-repairing efficiency of PBH-1 is tested by a tensile experiment, and the result shows that: the stress and the strain of the initial material are respectively 14.1MPa and 136.5%, and after repair, the stress and the strain are respectively 6.0MPa and 121.9%, and can be respectively recovered to 42.6% and 89.3% of the initial material, so that the material PBH-1 has good self-repair capability (figure 2).
Ultraviolet shielding test
The structure of the ultraviolet shielding test polyester is as follows:
The UV absorption capacity of the selected polyesters (PBH-1) was examined by the UV-Vis test, and commercial cosmetics, PBHG and PBHT were selected as controls. The test results show that PBH-1 has stronger absorption capacity to UVB wave band ultraviolet rays (figure 3). The data obtained by further calculation according to the relevant ultraviolet shielding formula show that: the UV absorption of PBH-1 in the UVB (280-320 nm) region was more than 2 times that of commercial materials and was superior to that of PBHG and PBHT (Table 2).
Table 2 PBH-1 ultraviolet shielding
Note that: commercial cosmetics use functionalized cinnamic acid nanofibers as a matrix, and sun-screening active ingredients: zinc oxide (14.5% wt%), octylmethoxy cinnamate (7.5% wt%) and caprylate (5% wt%).
Hydrophobic Property test
The structure of the hydrophobic property test polyester is as follows:
through the water contact angle test, it was found that the hydrophobic property was significantly improved with an increase in the number of fluorine atoms in the polyester (FIG. 4)
Degradation test
The structure of the degradation test polyester is as follows:
The degradation degree of the polyester material was tested by GPC after 15 days with a small amount of PTD with M n =29700 in phosphate buffer solution with ph=2 with stirring at room temperature for 15 days (fig. 5). The number average molecular weight of the polyester material is changed from 29700 to 19900, and the molecular weight distribution is changed from 1.39 to 2.08 (table 3), so that the polyester material has the degradable performance.
TABLE 3 specific data for polyester degradation
The foregoing is merely illustrative and explanatory of the invention as it is claimed, as modifications and additions may be made to, or similar to, the particular embodiments described, without the benefit of the inventors' inventive effort, and as alternatives to those of skill in the art, which remain within the scope of this patent.
Claims (9)
1. A multifunctional polyester material characterized in that the multifunctional polyester material has the following repeating structural units:
Wherein R 1 is aryl, aryl substituted with one or more R 1a, or electron withdrawing group; r 2 is hydrogen, alkyl or alkyl substituted with one or more R 1a; r 3 is aryl, aryl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, or electron withdrawing group; r 4 is hydrogen, alkyl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, aryl, or aryl substituted with one or more R 1a; r 5 is at least one of substituted aryl, heteroaryl, and alkyl; r 6 is formyl, acetyl, butyryl, pentanoyl, hexanoyl, propionyl, benzoyl, phenylacetyl, phenylpropionyl, phenylbutyryl, phenylpentanoyl, phenylhexanoyl, bromobenzoyl, chlorobenzoyl, fluorobenzoyl, trifluoromethylbenzoyl, naphthoyl, biphenyl acyl, methylbenzoyl, pyridine acyl, thiophene acyl or furan acyl; r 7、R8 and R 9 are each aryl, aryl substituted with one or more R 1a, heteroaryl, or heteroaryl substituted with one or more R 1a; r 1a is C 1～C10 alkyl, halogen, ester, cyano or amide; a. b and c are natural numbers in the range of 2 to 130.
2. The multifunctional polyester material of claim 1, wherein the aryl group has the structural formula:
3. the multifunctional polyester material of claim 1, wherein the electron withdrawing group has a structural formula as follows:
4. A method for producing a multifunctional polyester material according to any one of claims 1 to 3, comprising the steps of: adding a CO 2 -yl dimethyl glutarate compound and a functional diol monomer into a reaction device, continuously stirring under the protection of inert gas, heating to melt, and carrying out heat preservation reaction for 3-12 h; then heating to 200-240 ℃, reacting for 0.5-3 h under the vacuum degree of 450-500 Pa, continuing to react under the vacuum degree of 40-50 Pa until the pole climbing phenomenon occurs, and separating and purifying to obtain the multifunctional polyester material;
Wherein, the mol ratio of the CO 2 dimethyl glutarate compound to the functional diol monomer is 1:1-3;
the structural general formula of the CO 2 -yl dimethyl glutarate compound is shown as follows:
wherein R 1 is aryl, aryl substituted with one or more R 1a, or electron withdrawing group; r 2 is hydrogen, alkyl or alkyl substituted with one or more R 1a; r 3 is aryl, aryl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, or electron withdrawing group; r 4 is hydrogen, alkyl substituted with one or more R 1a, heteroaryl substituted with one or more R 1a, aryl, or aryl substituted with one or more R 1a; r 1a is C 1～C10 alkyl, halogen, ester, cyano or amide;
The structural formula of the functional diol monomer is shown as follows:
5. The method for producing a multifunctional polyester material according to claim 4, wherein the molar ratio of the CO 2 -yldimethyl glutarate compound to the functional diol monomer is 1:1 to 1.6.
6. Use of the multifunctional polyester material according to any of claims 1 to 3 for the preparation of uv-screening agents and/or for the preparation of hydrophobing agents and/or for the preparation of self-healing formulations.
7. A self-repairing agent characterized by using the multifunctional polyester material according to any one of claims 1 to 3 as a main component.
8. An ultraviolet shielding preparation characterized in that the multifunctional polyester material according to any one of claims 1 to 3 is used as a main component.
9. A hydrophobic preparation characterized by using the multifunctional polyester material according to any one of claims 1 to 3 as a main component.
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Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102676591A (en) * | 2012-01-12 | 2012-09-19 | 河南科技大学 | Method for preparing polyester containing 3-hydroxy glutaric acid unit |
| US9527952B1 (en) * | 2014-02-17 | 2016-12-27 | The University Of Toledo | Amorphous polyester from bio-based bis-furan assembly |
| KR101844998B1 (en) * | 2017-03-03 | 2018-04-03 | 한국화학연구원 | Self-healing polyester and film prepared by using the same |
| KR101931149B1 (en) * | 2018-06-04 | 2018-12-20 | 홍수동 | Unsaturated polyester resin with with excellent soft-fill property and polyurethane resin for paints using the same |
| CN109791224A (en) * | 2016-09-28 | 2019-05-21 | 三菱瓦斯化学株式会社 | Optics polyester film and transparent and electrically conductive film |
| CN111019101A (en) * | 2019-12-31 | 2020-04-17 | 绍兴惠群新材料科技有限公司 | Method for preparing PBT copolyester |
| CN111978528A (en) * | 2020-09-02 | 2020-11-24 | 浙江大学 | Method for synthesizing aromatic polyester without catalyst and product thereof |
-
2021
- 2021-11-02 CN CN202111289897.0A patent/CN116063666B/en active Active
Patent Citations (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN102676591A (en) * | 2012-01-12 | 2012-09-19 | 河南科技大学 | Method for preparing polyester containing 3-hydroxy glutaric acid unit |
| US9527952B1 (en) * | 2014-02-17 | 2016-12-27 | The University Of Toledo | Amorphous polyester from bio-based bis-furan assembly |
| CN109791224A (en) * | 2016-09-28 | 2019-05-21 | 三菱瓦斯化学株式会社 | Optics polyester film and transparent and electrically conductive film |
| KR101844998B1 (en) * | 2017-03-03 | 2018-04-03 | 한국화학연구원 | Self-healing polyester and film prepared by using the same |
| KR101931149B1 (en) * | 2018-06-04 | 2018-12-20 | 홍수동 | Unsaturated polyester resin with with excellent soft-fill property and polyurethane resin for paints using the same |
| CN111019101A (en) * | 2019-12-31 | 2020-04-17 | 绍兴惠群新材料科技有限公司 | Method for preparing PBT copolyester |
| CN111978528A (en) * | 2020-09-02 | 2020-11-24 | 浙江大学 | Method for synthesizing aromatic polyester without catalyst and product thereof |
Non-Patent Citations (2)
| Title |
|---|
| Electrochemical Ring-Opening Dicarboxylation of Strained Carbon-Carbon Single Bonds with CO2: Facile Synthesis of Diacids and Derivatization into Polyesters;Liao lili，等;Journal of the American Chemical Society;20220127;第144卷(第5期);2062-2068 * |
| 奇数-奇数脂肪族聚酯嵌段聚乳酸的研究;邵胜楠;中国优秀硕士学位论文全文数据库 工程科技Ⅰ辑;20200315;1-72 * |
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