Macromolecule hindered phenol antioxidant, preparation method of macromolecule hindered phenol antioxidant, and application of macromolecule hindered phenol antioxidant

A technology of hindered phenols and antioxidants, applied in the field of antioxidants, can solve the problems of large amount of addition, low antioxidant components, and further improvement of antioxidant performance, and achieve easy process control, large molecular weight, and convenient industrial production Effect

Inactive Publication Date: 2013-06-05
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, each molecular chain of this kind of polymer antioxidant has only two effective antioxidant groups, the effective antioxidant components are low, and the addition amount is large, and its antioxidant performance needs to be further improved.

Method used

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  • Macromolecule hindered phenol antioxidant, preparation method of macromolecule hindered phenol antioxidant, and application of macromolecule hindered phenol antioxidant
  • Macromolecule hindered phenol antioxidant, preparation method of macromolecule hindered phenol antioxidant, and application of macromolecule hindered phenol antioxidant
  • Macromolecule hindered phenol antioxidant, preparation method of macromolecule hindered phenol antioxidant, and application of macromolecule hindered phenol antioxidant

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0029] (1) Synthesis of sulfur-containing polyhydroxy polybutadiene: add 10.00 g of hydroxyl-terminated polybutadiene (Kray Willy (Guangzhou) Chemical Co., Ltd., Brand LBH2000, the number average molecular weight is 2.00×10 3, hydroxyl value 0.91mmol / g) and 5.00g tetrahydrofuran, the temperature was raised to 60°C, and magnetic stirring was performed to completely dissolve the hydroxyl-terminated polybutadiene (HTPB). Dissolve 0.200g of azobisisobutyronitrile and 2.00g of 2-mercaptoethanol in 10.00g of tetrahydrofuran, and add it dropwise to the above reactant within 30min, heat and react at 60°C for 3 hours, then transfer the reaction solution to a separate In the liquid funnel, after cooling to 25°C, add excess ice methanol to the separating funnel and oscillate, precipitate and separate into layers to obtain the crude product, then undergo dissolution-precipitation-separation for 5 times, and vacuum-dry at 60°C 12h to obtain sulfur-containing polyhydroxy polybutadiene. Th...

Embodiment 2

[0036] The difference between this example and Example 1 is that the amount of 2-mercaptoethanol in step (1) is changed to 5.00g, the amount of azobisisobutyronitrile is changed to 0.300g, the reaction time is 5h, and the constant temperature reaction temperature is 70°C . The hydroxyl value of the synthesized sulfur-containing polyhydroxy polybutadiene is 7.24mmol / g. In step (2), the mol ratio of isophorone diisocyanate and 2,2'-thiobis(4-methyl-6-tert-butylphenol) is changed into 1: 1.5, i.e. the ratio of isophorone diisocyanate The consumption is changed to 16.10g, and the consumption of 2,2'-thiobis(4-methyl-6-tert-butylphenol) is changed to 38.88g. by FT-IR and 1 Analysis such as H-NMR can show that the macromolecule hindered phenolic antioxidant has been successfully prepared.

[0037] The thermo-oxidative aging resistance and extraction resistance of the vulcanizate are shown in Table 1. It can be seen from Table 1 that the k value of natural rubber vulcanizate is 0...

Embodiment 3

[0039] This example differs from Example 1 in that the amount of 2-mercaptoethanol used in step (1) was changed to 1.00 g, azobisisobutyronitrile was changed to 0.050 g, the reaction time was 2 hours, and the constant temperature reaction temperature was 50°C. The hydroxyl value of the synthesized sulfur-containing polyhydroxy polybutadiene is 1.32mmol / g. Correspondingly, in step (2), the consumption of isophorone diisocyanate is changed to 2.93g, and the consumption of 2,2'-thiobis(4-methyl-6-tert-butylphenol) is changed to 9.45g. by FT-IR and 1 Analysis such as H-NMR can show that the macromolecule hindered phenolic antioxidant has been successfully prepared.

[0040] The thermo-oxidative aging resistance and extraction resistance of the vulcanizate are shown in Table 1. It can be seen from Table 1 that the k value of natural rubber vulcanizate after 48 hours of thermal oxygen accelerated aging at 100°C is 0.54; after soaking in 70°C water for 48 hours, and then 100°C ther...

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Abstract

The invention discloses a macromolecule hindered phenol antioxidant, a preparation method of the macromolecule hindered phenol antioxidant, and application of the macromolecule hindered phenol antioxidant. Under the action of thermal initiators, a sulfydryl-alkene click reaction is generated between sulfydryl in functional mercaptan and double bonds in hydroxyl-terminated polybutadiene under the temperatures of 50-70 DEG C to prepare sulfur-containing polyhydroxy polybutadiene; then under the temperatures of 30-50 DEG C, hydroxy in the sulfur-containing polyhydroxy polybutadiene reacts with secondary-position isocyanato in isophorone diisocyanate to obtain additive products secondary-position isocyanato-containing isocyanato; and then under the temperatures of 60-80 DEG C, the additive products react with bisphenols antioxidant to prepare the macromolecule hindered phenol antioxidant. The macromolecule hindered phenol antioxidant is good in thermo-oxidative aging performance, high in efficiency, and good in anti-extraction performance, and can be widely used in anti-aging of materials such as rubber and plastic.

Description

technical field [0001] The invention relates to the field of antioxidants, in particular to a macromolecule hindered phenolic antioxidant. The invention also relates to the preparation method and application of the macromolecule hindered phenolic antioxidant. Background technique [0002] During storage, processing, and use, polymer materials are subjected to heat, oxygen, ozone, etc., which will change the structure and performance of the material and gradually lose its use value. This phenomenon is called aging of polymer materials. Especially for rubber with a large number of double bonds in the molecular chain, the problem of thermo-oxidative aging is more prominent. In order to inhibit the aging of polymer materials, maintain the properties of materials, and prolong the life of materials, the most common and effective method is to add antioxidants to materials. Antioxidants mainly include amines, phenols, phosphorus and sulfur. Among them, the application of amine an...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/75C08G18/62C08G18/32C08F36/06C08F8/34C08L75/04C08L7/00C08L9/06C08L9/00C08J3/24
Inventor 曾幸荣吴文剑李红强赖学军郭建华王永洪李峰任晓康
Owner SOUTH CHINA UNIV OF TECH
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