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Polyester resin and method for producing the same

A polyester resin and oligomer technology, applied in the field of polyester resin and its preparation, can solve the problems of poor heat resistance, poor hydrolysis resistance of polyester resin, and inability to obtain high melting point polyester resin, etc., achieving high industrial value, The effect of excellent heat resistance

Inactive Publication Date: 2007-04-18
MITSUBISHI CHEM CORP
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  • Description
  • Claims
  • Application Information

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Problems solved by technology

(2) The disadvantage of the transesterification method is that the polyester resin obtained in this way has poor hydrolysis resistance, and the cost of ester-forming derivatives of 1,4-CHDA is higher than that of 1,4-CHDA
If the cis-isomer percentage of the 1,4-CHDA unit contained in the polyester resin increases, there is a problem that a polyester resin having a high melting point can hardly be obtained and has poor heat resistance
However, the literature does not suggest isomerization from trans to cis during polycondensation

Method used

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  • Polyester resin and method for producing the same
  • Polyester resin and method for producing the same

Examples

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preparation example Construction

[0029] In the production method of the present invention, the diol used in the esterification reaction preferably contains 1,4-CHDM. 1,4-CHDM in the diol is preferably at least 60 mol%, and if it is less than 60 mol%, the polymerizability will deteriorate.

[0030] In addition, from the viewpoint of availability, 1,4-CHDM is usually a mixture of trans-isomers and cis-isomers. However, it is desirable that the ratio of the trans isomer / cis isomer is usually selected from 100 / 0 to 60 / 40 in accordance with the required heat resistance and the like depending on the specific use. If the ratio of trans / cis is lower than 60 / 40, the heat resistance of the resulting polyester resin will be poor.

[0031] The diol component used to produce the polyester resin of the present invention is not particularly limited as long as it can be directly esterified with the above-mentioned dicarboxylic acid component. Diols containing 1,4-cyclohexanedimethanol (1,4-CHDM) are preferred. The proport...

Embodiment 1-1

[0091] In the reactor equipped with stirrer, distillation tube and decompression device, add 92.12g 1,4-CHDA (trans isomer / cis isomer=98 / 2), 79.07g 1,4-CHDM ( Adding molar ratio of CHDM / CHDA: 102.5 / 100) and 0.54g (0.31 mmol) of 10% by weight tetraethylammonium hydride aqueous solution, heated to 150° C. in an oil bath in a nitrogen stream, then heated to 200°C, and then kept at 200°C for 1 hour to carry out the esterification reaction. Then add 0.88g (0.155 mmol) n-butanol solution of 6% by weight tetra-n-butyl titanate to the reactor, and while raising the internal temperature from 200°C to 250°C in 45 minutes, gradually lower the temperature in the reactor. pressure for the polycondensation reaction. After maintaining the absolute pressure in the reactor at 0.1 kPa and reacting for 2.5 hours at a temperature of 250° C., the obtained polyester resin was pulled into water in the form of strands and pelletized. The intrinsic viscosity, melting point, and ratio of trans isomer...

Embodiment 1-2

[0093] The polycondensation reaction was carried out under the same conditions as in Example 1-1, except that the aqueous solution of 10% by weight of tetraethylammonium hydride was changed to an aqueous solution of 64 mg (0.078 mmol) of 10% by weight of sodium acetate. The intrinsic viscosity, melting point, and ratio of trans isomer / cis isomer in the 1,4-CHDA component of the obtained polyester resin are shown in Table 1-1.

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Abstract

The present invention provides a polyester resin having 1,4-CHDA as the main dicarboxylic acid units, having isomerization of trans-1,4-CHDA suppressed in the esterification and polyconsensation reactions and having a high melting point and excellent heat resistance, and a process for its production. A polyester resin obtainable by preparing an oligomer by an esterification reaction of a dicarboxylic acid component containing 1,4-cyclohexane dicarboxylic acid as the main component, with a diol component, and polycondensing this oligomer in the presence of a polycondensation catalyst; and a process for producing a polyester resin characterized in that the esterification reaction is carried out by means of a basic compound, and then, the polycondensation reaction is carried out by means of a polycondensation catalyst. In the resent invention, T0 and Tp satisfy 0 |{(T0-Tp) / T0}100 |12 where T0 is the mol% of the trans form in the 1,4-cyclohexane dicarboxylic acid contained in the starting material, and Tp is the mol% of the trans form in the 1,4-cyclohexane dicarboxylic acid units contained in the obtainable polyester resin.

Description

technical field [0001] The invention relates to a polyester resin and a preparation method thereof. More specifically, the present invention relates to a polyester resin excellent in heat resistance and hydrolysis resistance and a method for preparing the same. Background technique [0002] Among polyester resins, polyester resins containing 1,4-cyclohexanedicarboxylic acid (hereinafter sometimes abbreviated as 1,4-CHDA) units as main dicarboxylic acid units have excellent transparency, hydrolysis resistance (difficult to Hydrolysis properties), weather resistance, etc., so its use is constantly expanding. Can be by 1,4-CHDA or 1, the ester-forming derivative of 1,4-CHDA and glycol component carry out esterification reaction or transesterification reaction to obtain esterification reaction product (oligomer), in the presence of polycondensation catalyst, Polycondensation of this esterification reaction product yields a polyester resin containing 1,4-CHDA units as main dica...

Claims

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Application Information

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IPC IPC(8): C08G63/18C08G63/78
Inventor 明田美奈子笠井厚田中智彦
Owner MITSUBISHI CHEM CORP
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