Novel thiophenedicarboxylic acid-based copolyester as well as preparation method and application thereof

A technology of thiophenedicarboxylic acid-based copolyester and thiophenedicarboxylic acid, which is applied in the field of polymers, can solve the problems of polyester color yellowing and limited application range, and achieve high gas barrier performance, high light transmittance, and melt The effect of low viscosity

Active Publication Date: 2020-01-31
NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

They all belong to aliphatic polymers. Due to the lack of rigid aromatic ring structure in the molecular structure, their mechanical properties (such as strength, modulus, creep resistance, etc.) and heat resistance (such as thermomechanical properties, heat distortion temperature, etc.) are obvious. It is lower than petroleum-based polymer materials such as polyethylene terephthalate (PET), polycarbonate (PC), aromatic nylon (PA), bisphenol A epoxy resin (Epoxy), which severely limits their application. Application range
Polyethylene 2,5-furandicarboxylate (PEF) prepared from bio-based 2,5-furandicarboxylic acid and ethylene glycol has excellent mechanical properties, heat resistance and gas barrier properties, but polyester color The problem of yellowing has been difficult to solve

Method used

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  • Novel thiophenedicarboxylic acid-based copolyester as well as preparation method and application thereof
  • Novel thiophenedicarboxylic acid-based copolyester as well as preparation method and application thereof
  • Novel thiophenedicarboxylic acid-based copolyester as well as preparation method and application thereof

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preparation example Construction

[0024] One aspect of the embodiments of the present invention provides a method for preparing a novel thiophenedicarboxylic acid-based copolyester, comprising:

[0025] Under a protective atmosphere, make 2,5-thiophenedicarboxylic acid and / or 2,5-thiophenedicarboxylic acid ester, 2,4-thiophenedicarboxylic acid and / or 2,4-thiophenedicarboxylic acid ester, di A new type of thiophenedicarboxylic acid-based copolyester was obtained through the reaction of alcohols, catalysts, stabilizers and antioxidants.

[0026] Further, the catalyst includes esterification catalyst, transesterification catalyst and polycondensation catalyst.

[0027] In some more specific embodiments, the preparation method of the novel thiophenedicarboxylic acid-based copolyester specifically comprises: making 2,5-thiophenedicarboxylic acid and / or 2,5-thiophenedicarboxylic acid The mixture of esterified product, 2,4-thiophenedicarboxylic acid and / or 2,4-thiophenedicarboxylic acid esterified product, glycol, e...

Embodiment 1

[0054] Add 0.1mol of 2,5-thiophenedicarboxylic acid dimethyl ester, 0.1mol of 2,4-furandicarboxylic acid dimethyl ester, 0.32mol of ethylene glycol, and 0.0003mol of anhydrous zinc acetate into the reactor, pump Vacuum and nitrogen replacement three times, start stirring, gradually raise the temperature to 180 ° C, react for 3 hours, then add 0.0003 mol of antimony trioxide, 0.0004 mol of triphenyl phosphate, 0.00025 mol of tetrakis [β-(3,5-di-tert-butyl base-4-hydroxyphenyl)propionic acid]pentaerythritol ester, and then slowly evacuate to below 60Pa, and raise the temperature to 220°C, and react for 4.5h to obtain polyethylene thiophene dicarboxylate, which is polyethylene thiophene dicarboxylate ester 1 The data of H-NMR (deuterated trifluoroacetic acid as solvent) are: the hydrogen displacement of thiophene ring is 7.57ppm, 7.78ppm and 8.68ppm; the hydrogen atom displacement of ethylene glycol methylene is 4.20ppm.

[0055] After testing, the relative number-average molecu...

Embodiment 2

[0057] Add 0.16mol of dimethyl 2,5-thiophenedicarboxylate, 0.04mol of dimethyl 2,4-furandicarboxylate, 0.32mol of 1,3-propanediol, and 0.0004mol of anhydrous zinc acetate into the reactor , evacuate, replace with nitrogen for three times, start stirring, gradually raise the temperature to 180°C, react for 3 hours, then add 0.00045mol ethylene glycol antimony, 0.0006mol trimethyl phosphate, 0.0004mol tetrakis[β-(3,5-di tert-butyl-4-hydroxyphenyl) propionate] pentaerythritol ester, then slowly evacuate to below 60Pa, and raise the temperature to 210°C, and react for 3.0h to obtain poly(trimethylene thiophene dicarboxylate). After testing, poly(trimethylene thiophene dicarboxylate) The relative number-average molecular mass of the ester is 43000g / mol; the visible light transmittance is 89% (cut-off 700nm wavelength), the melt viscosity is lower than 720Pa·S at 220°C, and the glass transition temperature is 34.2°C; 5％ The thermal weight loss temperature is 385°C; the tensile stren...

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Abstract

The invention discloses novel thiophenedicarboxylic acid-based copolyester as well as a preparation method and application thereof. The novel thiophenedicarboxylic acid-based copolyester has a structure represented by the following formula: wherein m, n and x are all selected from 1-200, and R is an aliphatic chain or alicyclic ring with a C atom number of 2-20. The novel thiophenedicarboxylic acid copolyester provided by the invention has the characteristics of high visible light transmittance, low melt viscosity, good heat resistance, excellent mechanical property and gas barrier property and the like, and can be widely applied to the fields of barrier films, barrier bottles, fibers, engineering plastics and the like.

Description

technical field [0001] The invention belongs to the technical field of macromolecules, and in particular relates to a novel thiophenedicarboxylic acid-based copolyester as well as its preparation method and application. Background technique [0002] At present, the widely used bio-based polymer materials mainly include polylactic acid (PLA), polyhydroxy fatty acid (PHA), polyglycolic acid (PGA), polybutylene succinate (PBS) and so on. They all belong to aliphatic polymers. Due to the lack of rigid aromatic ring structure in the molecular structure, their mechanical properties (such as strength, modulus, creep resistance, etc.) and heat resistance (such as thermomechanical properties, heat distortion temperature, etc.) are obvious. It is lower than petroleum-based polymer materials such as polyethylene terephthalate (PET), polycarbonate (PC), aromatic nylon (PA), bisphenol A epoxy resin (Epoxy), which severely limits their application. application range. Polyethylene 2,5-fu...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/688C08G63/78
CPCC08G63/6886C08G63/78
Inventor 王静刚刘小青张小琴樊林朱锦
Owner NINGBO INST OF MATERIALS TECH & ENG CHINESE ACADEMY OF SCI
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