Poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester as well as preparation method and application thereof

A technology of propylene glycol ester and dimethyl, which is applied in the field of polymodified 2,2-dimethyl-1,3-propylene glycol ester and its preparation, can solve the problem that the strength, modulus and gas barrier properties are difficult to meet the application requirements, Reduced thermoplastic processing performance, low molecular weight of copolyester, etc., to achieve lower temperature, excellent thermoplastic processing performance, and increase molecular weight

Pending Publication Date: 2022-01-21
CHINA PETROLEUM & CHEM CORP +1
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] In addition, during the preparation process of copolyester, because the product is easily degraded by heating for a long time, the molecular weight of copolyester is low, and the strength, modulus and gas barrier properties are difficult to meet the application requirements.
In the prior art, polyhydric alcohols containing 3 or more hydroxyl groups such as glycerin and pentaerythritol and polyfunctional anhydrides are usually used to extend the polyester chain to increase the molecular weight of the copolyester. However, these chain extenders make the polyester form a network. Shaped cross-linked structure, thermoplastic processing performance is significantly reduced, thus affecting the application of copolyester

Method used

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  • Poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester as well as preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] Add 0.05mol dimethyl furandicarboxylate, 0.45mol dimethyl terephthalate, 0.8mol 2,2-dimethyl-1,3-propanediol, 0.00065mol anhydrous zinc acetate into a 1L reaction kettle, Vacuumize and replace with nitrogen three times, then raise the temperature to 195°C, and react for 4.5h. Then add 0.0005 mol antimony trioxide, 0.002 mol triphenyl phosphate, 0.001 mol antioxidant-1010, raise the temperature to 280°C, slowly evacuate to below 40Pa, react for 4.0 h, blow in nitrogen, add 0.00035 mol toluene diisocyanate (TDI), 280°C, continue to react for 0.6h to obtain poly-modified 2,2-dimethyl-1,3-propanediol ester.

[0033] The polymodified 2,2-dimethyl-1,3-propanediol ester obtained in this example has an intrinsic viscosity of 1.09 dL / g and a molecular weight of 6.5×10 4 g / mol, the tensile strength is 67.2MPa, the tensile modulus is 2.6GPa, and the carbon dioxide gas barrier performance is 1.3×10 -11 cm 3 cm / cm 2 ·s·cmHg, oxygen gas barrier performance is 1.0×10 -11 cm 3 cm...

Embodiment 2

[0035] Add 0.08mol dimethyl furandicarboxylate, 0.42mol dimethyl terephthalate, 0.8mol 2,2-dimethyl-1,3-propanediol, 0.00075mol anhydrous zinc acetate into a 1L reaction kettle, Vacuumize and replace with nitrogen three times, then raise the temperature to 190°C, and react for 5.0h. Then add 0.00075 mol of antimony trioxide, 0.001 mol of triphenyl phosphate, 0.0005 mol of antioxidant-1010, raise the temperature to 280°C, slowly evacuate to below 50Pa, react for 3.0 hours, blow in nitrogen, add 0.00025 mol of toluene diisocyanate (TDI), continue to react at 280°C for 1.0h to obtain poly-modified 2,2-dimethyl-1,3-propanediol ester.

[0036] The polymodified 2,2-dimethyl-1,3-propanediol ester obtained in this example has an intrinsic viscosity of 0.93 dL / g and a molecular weight of 5.4×10 4 g / mol, the tensile strength is 63.0MPa, the tensile modulus is 2.0GPa, and the carbon dioxide gas barrier performance is 1.2×10 -11 cm 3 cm / cm 2 ·s·cmHg, oxygen gas barrier performance is ...

Embodiment 3

[0038] Add 0.1mol dimethyl furandicarboxylate, 0.4mol dimethyl terephthalate, 0.8mol 2,2-dimethyl-1,3-propanediol, 0.0005mol anhydrous zinc acetate into a 1L reaction kettle, Vacuumize and replace with nitrogen three times, then raise the temperature to 190°C, and react for 4.0h. Then add 0.001mol antimony trioxide, 0.001mol triphenyl phosphate, and 0.001mol antioxidant-1076, raise the temperature to 260°C, slowly evacuate to below 20Pa, react for 4.0h, pass nitrogen gas, and add 0.001mol diphenyl Methane diisocyanate (MDI) was reacted at 260°C for 1.2 hours to obtain poly-modified 2,2-dimethyl-1,3-propanediol ester.

[0039] The intrinsic viscosity of the polymodified 2,2-dimethyl-1,3-propanediol ester obtained in this example is 1.07dL / g, and the molecular weight is 6.2×10 4 g / mol, the tensile strength is 65.7MPa, the tensile modulus is 2.1GPa, and the carbon dioxide gas barrier performance is 1.1×10 -11 cm 3 cm / cm 2 ·s·cmHg, oxygen gas barrier performance is 1.0×10 -11...

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Abstract

The invention discloses a poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester as well as a preparation method and an application thereof. The poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester is prepared from raw materials containing furandicarboxylic acid or an ester thereof, terephthalic acid or an ester thereof, 2, 2-dimethyl-1, 3-propylene glycol and a compound containing an isocyanate group through an esterification reaction and / or an ester exchange reaction, a condensation polymerization reaction and a chain extension reaction in sequence. The molecular weight of the copolyester is increased by introducing a compound containing an isocyanate group to react with hydroxyl-terminated or carboxyl-terminated polyester, and furandicarboxylic acid is introduced into a terephthalic acid 2, 2-dimethyl-1, 3-propylene glycol ester chain segment to improve the gas barrier property of the copolyester and increase the bio-based content, which can get rid of the dependence of the polyester industry on petroleum resources, and finally the poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester with high molecular weight, high gas barrier property and excellent mechanical properties is prepared. The poly-modified 2, 2-dimethyl-1, 3-propylene glycol ester provided by the invention can provide a new available material for the fields of packaging, films and the like.

Description

technical field [0001] The invention belongs to the technical field of polymer materials, and relates to a 2,2-dimethyl-1,3-propanediol ester and its preparation method and application, in particular to a polymer-modified 2,2, which can be used for packaging materials and film materials. 2-Dimethyl-1,3-propanediol ester and its preparation method and application. Background technique [0002] Polyethylene terephthalate (PET) is synthesized from terephthalic acid and ethylene glycol. It is widely used in chemical fiber, packaging materials, engineering plastics and other fields. The global annual output is more than 70 million tons, of which more than 40 million in China tons, and 80% is used for fiber manufacturing. Poly 2,2-dimethyl-1,3-propylene glycol terephthalate (PNT) is a new type of polyester with excellent performance after PET, which is composed of terephthalic acid and 2,2-dimethyl- It is formed by polycondensation of 1,3-propanediol ester. [0003] At present,...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G63/91C08G63/672C08G63/78C08G63/83C08G63/85C08G63/86C08L67/02
CPCC08G63/916C08G63/672C08G63/78C08G63/866C08G63/85C08G63/83C08L67/02C08L2203/16C08L2201/14
Inventor 王静刚戴钧明王树霞刘小青王玉合张小琴朱锦黄洛玮
Owner CHINA PETROLEUM & CHEM CORP
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