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Antioxidant and bisaminophenol derivative

a technology of bisaminophenol and bisaminophenol, which is applied in the field of antioxidants and aromatic hydroxyamine derivatives to achieve the effect of high oxidation-inhibiting properties

Inactive Publication Date: 2006-09-21
IDEMITSU KOSAN CO LTD
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

The present invention provides a new antioxidant that has excellent oxidation-inhibiting properties and can be used in plastics, rubbers, petroleum products, etc. The inventors found that aminophenol derivatives in which a hydroxyl group and an amino group are respectively bonded to adjacent ortho positions of an aromatic ring thereof exhibit an excellent oxidation-inhibiting property. Specifically, specific bisaminophenol derivatives are extremely effective in oxidation-inhibiting property. The present invention provides an antioxidant made of an aromatic hydroxyamine derivative having a specific structure and a bisaminophenol derivative. The antioxidant can be used in various products and the bisaminophenol derivative is a novel substance with excellent oxidation-inhibiting property.

Problems solved by technology

However, since oxidation products produced using the amine-based compounds tend to have a deep color, the use of the amine-based compounds must be limited to applications such as rubber products in which coloration of products causes no significant problems.

Method used

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  • Antioxidant and bisaminophenol derivative
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  • Antioxidant and bisaminophenol derivative

Examples

Experimental program
Comparison scheme
Effect test

example 1

Synthesis of 2-(isopropylamino)phenol

[0041] Into a 100 mL flask purged with nitrogen were added 12 g (109.92 mmol) of o-aminophenol and 60 mL of dimethylformamide (DMF), and the resultant mixture was stirred at room temperature and dissolved. Then, the obtained solution was mixed with 22.4 g (132 mmol) of 2-iodopropane such (molar ratio of 2-iodopropane to o-aminophenol: 1.2), and further with 11.4 g (114 mmol) of potassium hydrogencarbonate (KHCO3) as a catalyst, and the resultant mixture was stirred at room temperature for 5 h. After conducting the reaction for 5 h, 50 mL of water was added to the reaction solution to terminate the reaction.

[0042] As a result, it was confirmed that the rate of conversion of o-aminophenol was 72%, and the selectivity to the N-monoalkylated compound as produced (molar ratio of the monoalkylated compound to a sum of the mono- and di-alkylated compounds) was 73%.

[0043] The resultant reaction solution containing water was extracted with 50 mL of eth...

example 2

Synthesis of 2-(isopropylamino)phenol

[0044] The same procedure as in Example 1 was repeated except that the molar ratio of 2-iodopropane to o-aminophenol was changed to 1.0, the 2-iodopropane was dropped over 3 h, and then the reaction mixture was stirred at room temperature for 2 h.

[0045] As a result, it was confirmed that the rate of conversion of o-aminophenol was 58%, the selectivity to the N-monoalkylated compound was 99%, and the oxygen absorption initiation time as an index of determining an oxidation-inhibiting property thereof was 370 min.

example 3

Synthesis of 2-(isopropylamino)phenol

[0046] Into a 300 mL autoclave were charged 12 g (109.92 mmol) of o-aminophenol, 100 mL (79 g; 1.4 mol) of acetone, 0.6 g of Pd / C (Pd content: 5% by mass) and 30 g of MgSO4, and the contents of the autoclave were heated at 100° C. while stirring under a hydrogen pressure of 1.0 MPa. After the elapse of 1 h, the hydrogen absorption was ceased, and the reaction was terminated. The resultant reaction solution was subjected to suction filtration to remove Pd / C and MgSO4 therefrom, and the filtrate thus separated was concentrated and then mixed with water to crystallize a reaction product. The thus obtained reaction product was dried to obtain 2-(isopropylamino)phenol. As a result, it was confirmed that the yield of 2-(isopropylamino)phenol was 93%, and the oxygen absorption initiation time as an index of determining an oxidation-inhibiting property thereof was 370 min.

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Abstract

The present invention provides antioxidants made of an aromatic hydroxyamine derivative having a structure represented by the general formula (I): wherein R1, R2 and R3 are each independently a hydrogen atom or an alkyl group having 1 to 20 carbon atoms; X is a hydrogen atom or an OH group; Y is a hydrogen atom or an NHR1 group; A is a direct bond, —O—, —NH—, —SO2—, —CH2— or —C(CH3)2—, and when an OH group and an NHR1 group are introduced to a unilateral benzene ring, these groups are respectively bonded to adjacent positions of the benzene ring; and n is 0 or 1 with the proviso that when n is 0, R1 is not a hydrogen atom, as well as bisaminophenol derivatives represented by the above general formula (I) wherein n is 1; R2 and R3 are each a hydrogen atom; X is an OH group; Y is an NHR1 group; A is —C(CH3)2—; and R1 is isopropyl, isobutyl or isohexyl. The aromatic hydroxyamine derivatives having a structure represented by the general formula (I), in particular, the bisaminophenol derivatives as novel substances, exhibit an excellent oxidation-inhibiting property, and are usable as antioxidants or polymerization inhibitors.

Description

TECHNICAL FIELD [0001] The present invention relates to novel antioxidants and aromatic hydroxyamine derivatives, and more particularly to antioxidants made of aromatic hydroxyamine derivatives containing a hydroxyl group and an amino or monoalkylamino group respectively bonded to adjacent positions of an aromatic ring thereof which exhibit an excellent oxidation-inhibiting effect and are suitably used for plastics, rubbers, petroleum products, etc., as well as bisaminophenol derivatives. BACKGROUND ART [0002] Hitherto, antioxidants have been extensively used in various applications such as plastic products, rubber products, petroleum products (such as lubricating oils) and food. The antioxidants are mainly used for the purpose of inhibiting these products from suffering from undesirable change due to oxygen. [0003] There are conventionally known various kinds of antioxidants. Among these antioxidants, radical chain inhibitors (primary antioxidants) serve for capturing radicals prod...

Claims

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Application Information

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Patent Type & Authority Applications(United States)
IPC IPC(8): C09K15/16C07C215/76C08K5/00C08K5/18C09K15/24C09K15/28
CPCC07C215/76C08K5/005C08K5/18C09K15/24C09K15/28
Inventor SHIRAKI, YASUSHI
Owner IDEMITSU KOSAN CO LTD
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