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Double-hindered phenol structure-contained hydrazides compound and preparation method thereof

A technology of hindered phenols and hydrazides, which is applied in the field of hydrazides containing double hindered phenol structures and their preparation, and can solve the problems of low molecular weight, compatibility, yellowing resistance, migration resistance and insufficient antioxidant capacity , to achieve the effects of increased molecular weight, enhanced thermal oxidation resistance, and easy access to raw materials

Active Publication Date: 2012-02-08
YANTAI RUILONG CHEM TECH CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Problems solved by technology

[0004] However, due to the low molecular weight of traditional antioxidants or hydrazide anti-yellowing agents, there are many deficiencies in compatibility, anti-yellowing, anti-migration and anti-oxidation capabilities.

Method used

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  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof
  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof
  • Double-hindered phenol structure-contained hydrazides compound and preparation method thereof

Examples

Experimental program
Comparison scheme
Effect test

Embodiment 1

[0038] (2) Add 125g (0.5mol) methyl 3-methyl-4-hydroxy-5-tert-butylpropionate and 400ml methanol to a 1000ml three-neck flask, add 40% hydrazine hydrate 100g ( 0.8mol), stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure and dried to obtain 116.9 g of 3-methyl-4-hydroxy-5-tert-butylphenylpropanohydrazide, content ≥ 98.1% (HPLC), yield 93.5%, white powdery solid, Mp: 107-109°C.

[0039] (3) In a 500ml three-necked flask, add 50g (0.2mol) of 3-methyl-4-hydroxy-5-tert-butylphenylpropionohydrazide and 200mL of dichloromethane, and stir to dissolve. Cool down to 5-10°C, slowly add about 50ml of a dichloromethane solution of 25g 4,4'-diphenylmethane diisocyanate (MDI, 0.1mol) dropwise under stirring, and react at about 10°C for 5 hours after the dropwise addition is completed. Suction filtration and drying gave 70.1 g of white solid, content 98.5%, yield 93.4%, mp: 219-221°C. The final product structure is:

[0040] .

[0041] The NMR da...

Embodiment 2

[0045] (2) In a 1000ml three-necked flask, add 132g (0.5mol) ethyl 3-methyl-4-hydroxy-5-tert-butylpropionate and 400ml cyclohexane, and add 40wt.% hydrated Hydrazine 100g (0.8mol), stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure and dried to obtain 113.5 g of 3-methyl-4-hydroxy-5-tert-butylphenylpropanohydrazide, content ≥ 98.1% (HPLC), yield 90.8%, white powdery solid, Mp: 107-109°C.

[0046] (3) In a 500ml three-necked flask, add 50g (0.2mol) of 3-methyl-4-hydroxy-5-tert-butylphenylpropionohydrazide and 200mL of dichloromethane, and stir to dissolve. Cool down to 2-5°C, slowly add 23.6g of 4,4'-dicyclohexylmethane diisocyanate (HMDI, 0.09mol) in dichloromethane solution about 50ml dropwise under stirring, after the dropwise addition, react at about 5°C for 6 hours, filtered with suction, and dried to obtain 58.3 g of a white solid, with a content of 98.8%, and a yield of 85%. The final product structure is:

[0047] .

[0048...

Embodiment 3

[0050] (2) Add 125g (0.5mol) methyl 3-methyl-4-hydroxy-5-tert-butylpropionate and 400ml toluene to a 1000ml three-necked flask, add 40wt% hydrazine hydrate 100g ( 0.8mol), stirred at room temperature for 8 hours. The solvent was evaporated under reduced pressure and dried to obtain 115.4 g of 3-methyl-4-hydroxy-5-tert-butylphenylpropanohydrazide, content ≥ 98.5% (HPLC), yield 92.3%, white powdery solid, Mp: 107-109°C.

[0051] (3) In a 500ml three-necked flask, add 50g (0.2mol) of 3-methyl-4-hydroxy-5-tert-butylphenylpropionohydrazide and 200mL of dichloromethane, and stir to dissolve. Cool down to 5-10°C, slowly add about 60ml of a dichloromethane solution of 17.4g toluene diisocyanate (TDI, 0.1mol) dropwise under stirring, after the dropwise addition, react at about 10°C for 4 hours, filter with suction, and dry to obtain White solid 60.7g, content 99.0%, yield 90%. The final product structure is:

[0052] .

[0053] Example 4

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Abstract

The invention discloses a double-hindered phenol structure-contained hydrazides compound for a light stabilizer and a preparation method thereof. The double-hindered phenol structure-contained hydrazides compound has a double-hindered phenol and double-hydrazide structure, thus, the molecular weight is increased, and the migration resistance and thermal oxidation resistance capacity is strong. The preparation method comprises the following steps: performing addition reaction on hindered phenols and alpha, beta-acrylic ester under the action of a catalyst to obtain an addition product, wherein the molar ratio of the hindered phenols to the alpha, beta-acrylic ester is 1.0:(0.6-1.8), and the catalyst is alkali metal, an alkali metal hydroxide, an alkali metal hydride or an alkali metal alcoholate; then, performing carbonyl nucleophilic substitution reaction on the addition product and a hydrazine hydrate in an organic solvent A to obtain a hydrazides substitution product, wherein the molar ratio of the addition product to the hydrazine hydrate is 1.0:(0.8-5.0); performing the reaction between a diisocyanate compound and the hydrazides substitution product at the temperature of 0-10 DEG C; and carrying out recrystallization to obtain a goal product. By adopting the preparation method disclosed by the invention, the operation is simple, the raw materials are available, and the cost is low.

Description

technical field [0001] The invention relates to a hydrazide compound used as an anti-oxidation anti-yellowing agent and a preparation method thereof, in particular to a hydrazide compound containing a double hindered phenol structure and a preparation method thereof. Background technique [0002] Hindered phenolic compounds can inhibit the oxidative and thermal degradation of many organic compounds and polymers because they can capture peroxyl radicals. They are the most widely used antioxidants in the polymer industry, such as CIBA's antioxidants IRGANOX-1010, IRGANOX-245, IRGANOX-1076, antioxidant 1790 from CYTEC, USA, etc. Antioxidants are additives that inhibit or slow down the degradation of polymer materials due to oxidation. Therefore, the addition of antioxidants can effectively improve the heat resistance, light resistance, and oxidation resistance of polymer materials, and prolong the outdoor service life. [0003] Hydrazide anti-yellowing agents such as bis-(N,N...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C07C243/32C07C241/04C08L23/12C08K5/25
Inventor 姚建文王玉林
Owner YANTAI RUILONG CHEM TECH CO LTD
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