Ditetrahydrofurfuryl isophthalate-5-sulfonic acid and salt, preparation method and application thereof, and polylactic resin

A technology of ditetrahydrofurfuryl isophthalate and polylactic acid resin, applied in the field of preparation of polylactic acid resin, ditetrahydrofurfuryl isophthalate-5-sulfonic acid and its salts

Active Publication Date: 2013-07-31
吉林锦玉自动化设备科技有限公司
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

However, these nucleating agents have deficiencies in different aspects, so the development of new and efficient polylactic acid nucleating agents has important application value

Method used

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  • Ditetrahydrofurfuryl isophthalate-5-sulfonic acid and salt, preparation method and application thereof, and polylactic resin
  • Ditetrahydrofurfuryl isophthalate-5-sulfonic acid and salt, preparation method and application thereof, and polylactic resin
  • Ditetrahydrofurfuryl isophthalate-5-sulfonic acid and salt, preparation method and application thereof, and polylactic resin

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[0040] The present invention also discloses a preparation method of the ditetrahydrofurfuryl isophthalate-5-sulfonic acid, comprising the following steps:

[0041] Carrying out sulfonation reaction of isophthalic acid and sulfonating reagent to obtain 5-sulfoisophthalic acid;

[0042] The 5-sulfoisophthalic acid is acylated with an acylating agent, and then alcoholysed with tetrahydrofurfuryl alcohol to obtain ditetrahydrofurfuryl isophthalate-5-sulfonic acid.

[0043] In the process of preparing ditetrahydrofurfuryl isophthalate-5-sulfonic acid, the present invention uses isophthalic acid as a raw material to synthesize ditetrahydrofurfuryl isophthalate-5-sulfonic acid. According to the present invention, firstly, isophthalic acid is subjected to sulfonation reaction with a sulfonating agent to obtain 5-sulfoisophthalic acid. The sulfonating agent is preferably oleum, and the content of sulfur trioxide in the oleum is 20wt%-60wt%. The molar ratio of the sulfur trioxide to i...

Embodiment 1

[0062] Weigh 16.6 g of isophthalic acid, put it into a 250 mL three-necked round bottom flask equipped with a reflux condenser, add 25 mL of 20 wt % oleum, and heat the oil bath to 185 ° C for 6 hours under stirring conditions. After the reaction is over, remove the oil bath and cool to room temperature, dilute the reaction system, and cool sufficiently to precipitate 5-sulfoisophthalic acid. The excessive waste sulfuric acid was filtered off, and the obtained solid 5-sulfoisophthalic acid was added into a 250 mL three-neck round bottom flask. Add 70mL of thionyl chloride into a three-necked round-bottomed flask, heat and reflux at 80°C for 5 hours, after the reaction, transfer the reaction flask to an ice-water bath to cool, slowly add 15mL of tetrahydrofurfuryl alcohol dropwise to carry out the alcoholysis reaction, during the alcoholysis process Control the reaction temperature to 30°C. Ditetrahydrofurfuryl isophthalate-5-sulfonic acid can be obtained after separation and ...

Embodiment 2

[0066] Prepare ditetrahydrofurfuryl isophthalate-5-sulfonic acid according to the operation method described in Example 1. After the esterification reaction ends, add 40wt% potassium carbonate aqueous solution to the reaction system for neutralization, to pH After becoming neutral, filter and separate to obtain ditetrahydrofurfuryl isophthalate-5-potassium sulfonate.

[0067] The ditetrahydrofurfuryl isophthalate-5-potassium sulfonate obtained is carried out by nuclear magnetic resonance and infrared spectrum analysis, and the results are as follows: figure 1 and figure 2 as shown, figure 1 For the infrared spectrogram of ditetrahydrofurfuryl isophthalate-5-potassium sulfonate prepared in Example 2 of the present invention, figure 2 For the ditetrahydrofurfuryl isophthalate-5-potassium sulfonate prepared in Example 2 of the present invention 1 H NMR spectrum. Depend on figure 1 It can be seen that 3068cm -1 The C-H stretching vibration peak of the benzene ring appears ...

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Abstract

The invention provides ditetrahydrofurfuryl isophthalate-5-sulfonic acid, ditetrahydrofurfuryl isophthalate-5-sulfonate, a preparation method and an application thereof, and polylactic resin. According to the invention, isophthalic acid is adopted as a raw material, and a sulfonation reaction is carried out, such that 5-sulfoisophthalic acid is synthesized; an acylation reaction is carried out, and an alcoholysis reaction is carried out with tetrahydrofurfuryl alcohol, such that ditetrahydrofurfuryl isophthalate-5-sulfonic acid is obtained. The obtained ditetrahydrofurfuryl isophthalate-5-sulfonic acid is subjected to a reaction with one of metal, metal oxide, metal hydroxide, and metal salt, such that ditetrahydrofurfuryl isophthalate-5-sulfonate is obtained. The obtained ditetrahydrofurfuryl isophthalate-5-sulfonic acid or salt thereof can be used in a nucleating agent of polylactic resin. Experiment results show that polylactic resin crystallization rate and crystallinity are substantially improved.

Description

technical field [0001] The technical field of compounds of the present invention, in particular, relates to ditetrahydrofurfuryl isophthalate-5-sulfonic acid and its salt, preparation method and application, and polylactic acid resin. Background technique [0002] Polylactic acid (PLA) is a synthetic thermoplastic aliphatic polyester, which has become a research hotspot in recent years. Since the lactic acid monomer of polylactic acid is fermented from starch, polylactic acid is renewable; at the same time, polylactic acid resin has excellent biodegradability and biocompatibility, and finally decomposes into CO in the environment. 2 and H 2 O, so polylactic acid is non-polluting. Not only that, many performance indicators of polylactic acid are similar to those of general-purpose plastics such as polyethylene, polypropylene or polystyrene, and it has broad application prospects. It is the most promising biomedical material and packaging material. [0003] Although polylac...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07D307/12C08G63/688
CPCY02P20/582
Inventor 孙志强张涵庞烜庄秀丽陈文啟陈学思
Owner 吉林锦玉自动化设备科技有限公司
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