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Macromolecular hindered phenol antioxidant containing thioether and carbamate group and preparation method and application thereof

A technology of urethane-based and hindered phenol antioxidants, which is applied in the field of macromolecular hindered phenol antioxidants and its preparation, can solve the problems of large addition amount and low content of antioxidant groups, and achieve small addition amount, Effect of high molecular weight and high yield

Inactive Publication Date: 2016-03-02
SOUTH CHINA UNIV OF TECH
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

However, this kind of macromolecular antioxidant has low effective antioxidant group content and a large amount of addition. Usually, the amount of addition needs 8 to 10 parts to achieve the antioxidant effect of 1 part of the corresponding small molecule antioxidant (Synthesis and thermo-oxidative aging resistance of hydroxylterminated polybutadiene-bound2,2 -thiobis(4-methyl-6-tert-butylphenol). Polymer-Plastics Technology and Engineering. 2012, 51, 1006-1013.)

Method used

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  • Macromolecular hindered phenol antioxidant containing thioether and carbamate group and preparation method and application thereof
  • Macromolecular hindered phenol antioxidant containing thioether and carbamate group and preparation method and application thereof
  • Macromolecular hindered phenol antioxidant containing thioether and carbamate group and preparation method and application thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0032] (1) Synthesis of hindered phenol intermediates containing alcoholic hydroxyl groups and thioether groups: Dissolve 0.02mol of antioxidant GM and 0.04mol of 2-mercaptoethanol (ME) in a 150mL three-neck flask equipped with magnetic stirring and condenser Obtain reactant toluene solution in 50g toluene; Dissolve 0.80mmol triethylamine in 10g toluene to obtain triethylamine toluene solution. At 50°C, the triethylamine toluene solution was added dropwise to the reactant toluene solution within 30 min. After constant temperature reaction for 3 hours, it was transferred to a round-bottomed flask, and toluene and excess 2-mercaptoethanol were distilled off under reduced pressure at 100°C to obtain a hindered phenol intermediate GM-ME containing alcoholic hydroxyl groups and thioether groups. The molecular structure of antioxidant GM and hindered phenol intermediate GM-ME containing alcoholic hydroxyl group and thioether group is as follows:

[0033]

[0034] FT-IR on GM and...

Embodiment 2

[0040] This example differs from Example 1 in that 2-mercaptoethanol is replaced by 6-mercaptohexanol (MH) in step (1), the reaction temperature is 30°C, and the reaction time is 6h; the macromolecular antioxidant yield is 94.6%. From FT-IR, 1 H-NMR and MALDI-TOF-MS analysis showed that the macromolecular hindered phenol antioxidant GM-MH-TDI containing thioether and carbamate groups was successfully prepared, the molecular weight was 1230g / mol, and its structural formula was as follows. The retention rate of mechanical properties of natural rubber vulcanizates after aging at 100°C for 72 hours is shown in Table 1. It can be seen from Table 1 that after aging at 100°C for 72 hours, 2 phr of the macromolecular hindered phenol antioxidant GM-MH-TDI synthesized in this example containing thioether and carbamate groups was added to the natural rubber vulcanizate Tensile strength and elongation retention at break were 91.2% and 80.9%, respectively. Compared with Example 1, the c...

Embodiment 3

[0043] The difference between this embodiment and Example 1 is that the toluene diisocyanate (TDI) in the step (2) is replaced by p-phenylene diisocyanate (PPDI), the consumption of dibutyltin dilaurate is 0.05mmol, and the reaction temperature is 60°C. The reaction time is 4h, and the yield of macromolecular antioxidant is 96.3%. From FT-IR, 1 H-NMR and MALDI-TOF-MS analysis showed that the macromolecular hindered phenol antioxidant GM-ME-PPDI containing thioether and carbamate groups was successfully prepared, the molecular weight was 1104g / mol, and its structural formula was:

[0044]

[0045] The retention rate of mechanical properties of the vulcanizate after aging at 100°C for 72 hours is shown in Table 1. It can be seen from Table 1 that after aging at 100°C for 72 hours, 2 phr of the macromolecular hindered phenol antioxidant GM-ME-PPDI synthesized in this example containing thioether and carbamate groups was added to the natural rubber vulcanizate Tensile strengt...

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Abstract

The invention discloses a macromolecular hindered phenol antioxidant containing thioether and carbamate groups and a preparation method and application thereof. In the role of a tertiary amine catalyst, thiol-ene click reaction of a bisphenol mono acrylate compound and functional thiol containing hydroxyl is performed at 30-50DEG C to prepare a hindered phenol intermediate containing alcoholic hydroxyl and thioether groups; under the action of a dibutyltin dilaurate catalyst, the hindered phenol intermediate containing alcoholic hydroxyl and thioether groups is reacted with an organic diisocyanate compound at 50-70 DEG C to prepare the macromolecular hindered phenol antioxidant containing the thioether and carbamate groups. The macromolecular hindered phenol antioxidant has the characteristics of excellent anti heat and oxygen aging performance and high efficiency, and can be widely used in ageing prevention of rubber and other materials.

Description

technical field [0001] The invention relates to the field of antioxidants, in particular to a macromolecular hindered phenol antioxidant containing sulfide and carbamate groups, a preparation method and application thereof. Background technique [0002] The phenomenon that polymer materials are subjected to heat and oxygen during storage, processing or use, causing the materials to oxidize and gradually lose their use value is called thermal oxygen aging. Especially for rubber with a large amount of carbon-carbon double bonds in the molecular chain, the problem of thermo-oxidative aging is more prominent. In order to inhibit the aging of polymer materials and prolong the service life of materials, the most common and effective method is to add antioxidants to materials. Antioxidants can be divided into primary antioxidants and secondary antioxidants according to different modes of action. Primary antioxidants mainly include aromatic amines, hindered phenols, etc., and secon...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07C323/52C07C319/20C08L7/00C08L9/06C08L9/00C08L75/04C08K13/02C08K5/375
Inventor 曾幸荣吴文剑李红强赖学军谢湖
Owner SOUTH CHINA UNIV OF TECH
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