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Plasticizing, oxidation resistance and thermal stabilization modifying agent of PVC material and preparation method thereof

A PVC material, anti-oxidation technology, applied in chemical instruments and methods, preparation of organic compounds, preparation of carboxylic acid esters, etc., can solve the problems of limited catalyst application, high toxicity of organic mercury, easy dehydration of hydroxyl groups into ethers, etc.

Inactive Publication Date: 2010-02-17
HEBEI JINGXIN CHEM GRP CO LTD
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  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] There are many reports on the formation of esters of 2-butyne-1,4-diol. In view of the problem that the propargyl alcohol hydroxyl group is easily dehydrated into ether under acid catalysis, the acid chloride of carboxylic acid is usually used in organic bases such as triethylamine, It is completed in the presence of pyridine or inorganic bases, but the acid chloride method requires a large amount of organic bases, and the post-treatment is difficult
2-butyne-1,4-diol and 3,5-di-tert-butyl-4-hydroxyphenylpropionate methyl ester are both convenient and easy-to-obtain raw materials, and their transesterification reactions have not been reported
However, organic mercury is more toxic, which limits the application of this type of catalyst
In its patent (DE805760), BASF uses copper acetate or copper acetate / copper powder as a catalyst to realize 2-butyne-1,4-diol diacetate and 2-butyne-1,4-diol Nucleophilic addition reaction of bisbenzyl ether with acetic anhydride, but the yield is low

Method used

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  • Plasticizing, oxidation resistance and thermal stabilization modifying agent of PVC material and preparation method thereof
  • Plasticizing, oxidation resistance and thermal stabilization modifying agent of PVC material and preparation method thereof
  • Plasticizing, oxidation resistance and thermal stabilization modifying agent of PVC material and preparation method thereof

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Experimental program
Comparison scheme
Effect test

Embodiment 1

[0027] Preparation of 2-butyne-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionate) ester

[0028] Install a 500mL round bottom flask on a magnetic stirring electric heating mantle, add 2-butyne-1,4-diol 17.2g (0.2mol), solvent 200mL, 3,5-di-tert-butyl-4-hydroxyphenylpropane Acetate methyl ester 117g (0.4mol), catalyzer (0.01mol), put on the fractionation column (built-in glass filler) that height is 60cm, install distillation head and straight condenser tube on the top of fractionation column, adjust the voltage, slowly heat and reflux for 1 Hour. Then slightly increase the voltage to control the temperature at the top of the fractionation column to not exceed 68°C. The generated methanol was gradually distilled off, and the reaction was stopped when the amount of methanol reached 20 mL. Pour out the reaction solution while hot. Cool and filter the resulting solid. Dry naturally, weigh, and calculate the crude yield. The crude product was recrystallized with an equa...

Embodiment 2

[0036] Preparation of 2-lauroyloxy-2-butene-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionate) ester.

[0037] In a 500mL three-necked flask equipped with mechanical stirring, add 2-butyne-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionic acid) ester 60.7 through crystallization purification in Example 1 g (0.1mol), lauric acid (n-dodecanoic acid) 20.0g (0.1mol), catalyst (0.002mol). Install a reflux condenser and a thermometer, heat up to a certain temperature and stir the reaction until the TLC detects that the raw material point disappears, cool to 80°C, add 200mL cyclohexane to reheat and dissolve, filter while it is hot, and the filtrate cools to precipitate white flaky crystals, the result Listed in Table 3. 2-lauroyloxy-2-butene-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionate) ester, melting point: 104-106°C. 1 H NMR (500MHz, CDCl 3 ): δ6.95(4H, s), 5.56(2H, s), 5.26(1H, t, J=6.5Hz), 5.12(2H, d, J=6.5Hz), 5.00(2H, s), 2.96 -2.85 (4H, m), 2.65-2....

Embodiment 3

[0043] Preparation of 2-palmitoyloxy-2-butene-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionate) ester

[0044] Add the 2-butyne-1,4-diol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionic acid) ester through crystallization and purification in a 500mL three-necked flask equipped with mechanical stirring 60.7g (0.1mol), palmitic acid (hexadecanoic acid) 25.6g (0.1mol), cuprous acetate 0.245g (0.002mol). Install the upper reflux condenser and thermometer, raise the temperature to 135°C and stir for 11 hours until the raw material point disappears as detected by TLC, cool to 80°C and add 200mL cyclohexane to reheat to dissolve, filter while hot, the filtrate cools and precipitates white flaky crystals 80.3 g, yield: 93.0%, melting point: 97-99°C. 1 H NMR (500MHz, CDCl 3 ): δ6.98(4H, s), 5.52(2H, s), 5.24(1H, t, J=6.0Hz), 5.12(2H, d, J=6.0Hz), 5.01(2H, s), 2.95 -2.85 (4H, m), 2.65-2.48 (6H, m), 1.50 (2H, m), 1.35-1.20 (60H, m), 0.92 (3H, t, J=7.5Hz). Elemental analysis (C ...

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Abstract

The invention provides a plasticizing, oxidation resistance and thermal stabilization modifying agent of PVC material and a preparation method thereof, and the modifying agent is an organic compound.The preparation method comprises the following steps: 2-butine-1, 4-diol and 3,5-tert butyl-4-hydroxyphenyl propionic acid methyl ester carry out ester exchange reaction in an organic solvent under the action of an organic base catalyst to obtain 2-butine-, 4-diol dibasic acid (3,5- tert butyl-4-hydroxyphenyl propionic acid) esters; the 3,5- tert butyl-4-hydroxyphenyl propionic acid and a long-chain fatty acid carry out nucleophilic addition under the action of a cuprous salt catalyst to generate 2-fat acyloxy-2-butylene-1 and 4-diol dibasic acid (3,5-tert butyl-4-hydroxyphenyl propionic acid)esters. The main body of the compound is a triester which has the function of a plasticizer, and the 3,5- tert butyl-4-hydroxyphenyl propionic acid parts at two ends have the functions of catching free radicals and preventing PVC from being oxidized. Carbon-carbon double bond which is activated by acyloxy at the center is easy to carry out rapid addition with chlorine hydride, thereby preventingPVC from decomposing and changing color and playing the role of a heat stabilizer for PVC hot processing.

Description

technical field [0001] The invention relates to a plasticizing, anti-oxidation and heat-stabilizing modifier for PVC materials, belonging to the technical field of fine chemicals and their synthesis methods, in particular to 2-fatty acyloxy-2-butene-1,4-di Alcohol bis(3,5-di-tert-butyl-4-hydroxyphenylpropionate) compound and a preparation method thereof, the compound is used for plasticizing, anti-oxidation and thermal stability modification of PVC materials. Background technique [0002] PVC is a widely used polymer material. PVC must be heated during the processing and forming process to make it plastic, but a certain degree of decomposition will inevitably occur during the heating process, mainly due to elimination reactions to generate carbon-carbon double bonds and hydrogen chloride. If there is no stabilizer, the generated hydrogen chloride will further catalyze the decomposition of PVC, resulting in a conjugated polyene structure, which will make the product discolor...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08K5/134C08L27/06C07C67/04C07C69/732
Inventor 张保发王兴为
Owner HEBEI JINGXIN CHEM GRP CO LTD
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