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2,5-furan dicarboxylic acid copolyester and preparation method thereof

A technology of furandicarboxylic acid copolyester and furandicarboxylic acid, which is applied in the field of copolyester modification, can solve the problems of decreased quantity, low elongation at break, low Young's modulus, etc., and achieves the effect of improving flexibility

Active Publication Date: 2018-07-10
CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

Using 2,2,4,4-tetramethyl-1,3-cyclobutanediol to copolymerize with FDCA and EG, the corresponding Young’s modulus of the copolymer increased from 2800±120MPa of PEF to 3300±100MPa, but the copolymerization The elongation at break (4±1%) of polymers was not improved compared with that of PEF (5±1%) (Polymers, 2017, 9(9):305-320.) These findings suggest that the use of The flexible monomer-modified FDCA polyester can improve the elongation at break, but the Young's modulus of the copolymer is an order of magnitude lower than that of the original homopolymer, and the modified monomer with too strong rigidity will make the Young's modulus The amount can be further increased without increasing the elongation at break
[0005] To sum up, after adding modified monomers to the existing polyester materials, either the elongation at break is too low, or the Young's modulus is too low, and there is a lack of a high elongation at break while maintaining a high Young's modulus. modulus of polyester

Method used

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Examples

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preparation example Construction

[0034] A method for preparing the above 2,5-furandicarboxylic acid copolyester, comprising the following steps:

[0035] [1] Under an inert gas atmosphere, mix 2,5-furandicarboxylic acid monomer, glycol, modified dibasic acid monomer and catalyst in proportions, and heat to generate esterification reaction. The heating temperature is preferably 90-240 ℃, the reaction time is 1-12 hours.

[0036] The 2,5-furandicarboxylic acid monomer is 2,5-furandicarboxylic acid or 2,5-furandimethyl; the modified dibasic acid monomer is 1,4-cyclohexanedicarboxylic acid, 1 , 4-cyclohexane dimethyl, isoidose dicarboxylic acid or isoidose dimethyl ester; the diol can choose one or more hydrocarbon or heterocyclic diols.

[0037] [2] The temperature of the mixture obtained through the esterification reaction in step [1] is further increased, and the increased temperature is 90-270°C. The pressure of the environment where the mixture is located is reduced from atmospheric pressure to below 100 Pa, the ...

Embodiment 1

[0045] [1] Put ethylene glycol, 2,5-furandicarboxylic acid and 1,4-cyclohexanedicarboxylic acid (molar ratio 5:1:1) in the reactor, and add isopropyl titanate (the number of moles is 0.1% of the total moles of 2,5-furandicarboxylic acid and 1,4-cyclohexanedicarboxylic acid) are used as catalysts for transesterification and polycondensation, and nitrogen gas is introduced and fully stirred. The uniformly mixed reactants are heated to 160°C for 1 hour, 170°C for 1 hour, 180°C for 1 hour, and 190°C for 2 hours, so that the reactants undergo an esterification reaction.

[0046] [2] Raise the temperature to 210°C again, slowly reduce the pressure of the reaction system from atmospheric pressure to below 100Pa within 0.5 hours, react for 1 hour, keep the vacuum below 100Pa, then heat up to 220°C for 2 hours, and then heat up to 230°C for reaction For 2 hours, the esterified product was subjected to polycondensation reaction to obtain poly(ethylene 2,5-furandicarboxylate-co-1,4-cyclohex...

Embodiment 2

[0049] [1] Put ethylene glycol, 2,5-furandicarboxylic acid and 1,4-cyclohexanedicarboxylic acid (molar ratio 6.67:2.33:1) in the reactor, and add butyl titanate (mole number is 2 0.1% of the total moles of 1,5-furandicarboxylic acid and 1,4-cyclohexanedicarboxylic acid) are used as a catalyst for transesterification and polycondensation, and nitrogen gas is introduced and fully stirred. The uniformly mixed reactants are heated to 180° C. for 5 hours to make the reactants undergo an esterification reaction.

[0050] [2] Increase the temperature to 210°C, slowly reduce the pressure of the reaction system from atmospheric pressure to below 100 Pa within 0.5 hours, react for 1 hour, keep the vacuum below 100 Pa, and then heat up to 220°C for 4 hours to perform polycondensation of the esterified product The reaction obtains polyethylene 2,5-furandicarboxylate-co-1,4-cyclohexanedicarboxylate.

[0051] Measured by the polymer tensile experiment, the Young’s modulus E of the polyethylene ...

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Abstract

The invention relates to the technical field of modification of copolyester, and in particular, relates to 2,5-furan dicarboxylic acid copolyester and a preparation method thereof. In allusion to theproblems that after a modification monomer is added to a conventional polyester material, either the elongation at break is too low or the young's modulus is too low, and polyester having high elongation at break and also maintaining high Young's modulus is lack, the technical scheme comprises that provided is the 2,5-furan dicarboxylic acid copolyester having the following structural formula defined in the specification, wherein R1 in the structural formula is a repeating unit of a group defined in the specification, R2 and R4 in the structural formula are hydrocarbon or heterocyclic repeating units, and R3 in the structural formula is a repeating unit containing six-membered fatty cyclic hydrocarbons or a repeating unit containing multiple saturated five-membered heterocyclic rings. Theinvention also provides the preparation method of the 2,5-furan dicarboxylic acid copolyester. The 2,5-furan dicarboxylic acid copolyester is suitable for packaging materials, textiles, engineering plastics and other fields.

Description

Technical field [0001] The invention relates to the technical field of copolyester modification, in particular to a 2,5-furandicarboxylic acid copolyester and a preparation method thereof. Background technique [0002] Polyester terephthalate is a kind of thermoplastic material with excellent properties, such as polyethylene terephthalate (PET), polytrimethylene terephthalate (PPT) and polybutylene terephthalate Glycol esters (PBT), PET and PBT have been widely used in packaging materials, textiles, engineering plastics and other fields. The main raw materials for the preparation of terephthalic acid polyester are terephthalic acid (PTA) and glycol. So far, PTA is mainly derived from petroleum resources and is not renewable. In addition, the preparation of PTA from petroleum resources causes environmental problems. Larger pollution. Therefore, it is of great significance to develop a renewable monomer that can replace PTA. 2,5-Furandicarboxylic acid (FDCA) is a renewable bioma...

Claims

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Application Information

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IPC IPC(8): C08G63/672C08G63/87C08G63/85C08G63/78
CPCC08G63/672C08G63/78C08G63/85C08G63/87
Inventor 王公应王贤松王庆印曾毅
Owner CHENGDU ORGANIC CHEM CO LTD CHINESE ACAD OF SCI
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