Phenylenediamine derivative, production method thereof and antioxidant for rubber using it as effective constituent

Inactive Publication Date: 2005-07-21
NOK CORP
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0046] According the present invention, the phenylenediamine derivatives (I) and (II) have an excellent in the dispersability into rubbers and in the thermal stability even in the case of being used under a high-temperature condition. So the antioxidants of the present invention can be effectively used as antioxidants for rubbers, etc.
[0047] The phenylenediamine derivatives (I) and (II) have also an excellent property in the point of the oil-extraction resistance even in the case of being added to a sealing material which is brought into contact with an engine oil, so these phenylenediamine derivatives can be effectively used i

Problems solved by technology

These materials are usually used at a temperature of from about 100 to 150° C., so it is sufficient that the antioxidants used in these materials have a temperature resistance of up to about 150° C., and there have been almost no antioxidant that is assumed to be used at a temperature higher than 150° C. Accordingly, when these antioxidants are used at a temperature higher than 150° C., these antioxidants are apt to volatile from the surface of the materials making it difficult to prolong the life of the materials.
Also, to realize the low volatility of an antioxidant, an attempt of chemically bonding the antioxidant molecule to a polymer and an attempt of holding the antioxidant to a porous substance have been carried out, but there have been many problems in practical use of these methods and the above-described attempts have not yet been practically used at present.
In particular, in the case of an acrylic rubber, an antioxidant is incorporated into the rubber for the purpose of prolonging the life thereof but the antioxidants proposed until now are yet insufficient and a more improvement has been desired.
To hold an antioxidant in a rubber for a long period of time, an attempt of increasing the molecular weight of the antioxidant, an attempt of bonding the antioxidant to a polymer, etc., have been practiced until now as described above, but in the case of using an antioxidant for an acrylic rubber, in particular for an acrylic rubber as

Method used

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  • Phenylenediamine derivative, production method thereof and antioxidant for rubber using it as effective constituent
  • Phenylenediamine derivative, production method thereof and antioxidant for rubber using it as effective constituent
  • Phenylenediamine derivative, production method thereof and antioxidant for rubber using it as effective constituent

Examples

Experimental program
Comparison scheme
Effect test

example 1

(Production of Antioxidant 1)

[0050] In a 500 ml three-necked flask on an oil bath were placed 52.0 g of N,N′-diphenyl-1,4-phenylenediamine (Nocrac DP, a trade name made by Ouchi Shinko Kagaku K.K.) and 74.9 g of 4-(1-propenyl)-1,2-dimethoxybenzene and after sufficiently replacing the atmosphere with a nitrogen gas with stirring, the temperature of the oil bath was increased to 140° C. Thereafter, 5 g of concentrated sulfuric acid was added dropwise from a dropping funnel to the mixture over a period of about 30 minutes, and when after finishing the addition, the reaction was further continued for about 15 hours, the viscosity of the reaction mixture was increased with the passage of time. After the reaction was over, toluene was added to the reaction mixture to form a toluene solution, then the toluene solution was poured into an excessive amount of an aqueous sodium hydroxide solution, followed by stirring, and then a lower layer (aqueous solution layer) formed was separated by a...

example 2

(Production of Antioxidant 2)

[0055] By following the same procedure as in Example 1 except that the amount of N,N′-diphenyl-1,4-phenylenediamine was changed to 78.0 g and 99.5 g of 4-tert-butylstyrene was used in place of the 4-(1-propenyl)-1,2-dimethoxybenzene, 139.0 g (yield 80%) of the desired product was obtained.

[0056] The weight loss of the product at 175° C. for 40 hours was lower than 10% (6.2%) and the behaviors of the product by the TLC method were substantially the same as those in Example 1. Mn (by a GPC method using tetrahydrofuran as the solvent): 700 FI-IR (measured by casting on a KRS-5 crystal plate): FIG. 2 1H-NMR (CDCl3, 25° C.): [0057] near 1.22 ppm (CH3 group) [0058] near 7.1 ppm (aromatic H)

Presumed Structure:

example 3

(Production of Antioxidant 3)

[0059] By following the same procedure as in Example 1 except that 62.2 g of anethol-(p-methoxypropenylbenzene) was used in place of the 4-(1-propenyl)-1,2-dimethoxybenzene, 94.6 g (yield 85%) of a blackish brown desired product was obtained.

[0060] The weight loss of the product at 175° C. for 40 hours was lower than 10% (8.6%) and the behaviors of the product by the TLC method were substantially the same as those in Example 1. Mn (by a GPC method using tetrahydrofuran as the solvent): 704 FI-IR (measured by casting on a KRS-5 crystal plate): FIG. 3 1H-NMR (CDCl3, 25° C.): [0061] near 0.88 ppm (CH3 group) [0062] near 3.8 ppm (OCH3 group) [0063] near 6.8 to 7.2 ppm (aromatic H)

Presumed Structure:

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Abstract

A phenylenediamine derivative represented by following formula (I) or (II):
wherein R1 and R2 each represents a hydrogen atom, a lower alkyl group, or a lower alkoxy group; R3 represents a hydrogen atom or a methyl group; R4 represents a methyl group or an ethyl group; and n and m each is 1, 2, or 3;
wherein R1 and R2 each represents a hydrogen atom, a lower alkyl group, a lower alkoxy group, or a cyano group; and n and m each is 1, 2, or 3, is disclosed.
These phenylenediamine derivatives are effectively used as antioxidants for rubbers, which scarcely cause vanishing by evaporation or a thermal denaturation even under a high-temperature condition of 150° C. or higher.

Description

FIELD OF THE INVENTION [0001] The present invention relates to a phenylenediamine derivative, a production method thereof, and an antioxidant for rubber using the phenylenediamine derivative as the effective constituent. More specifically, the present invention relates to a phenylenediamine derivative which is stable at a high temperature of 150° C. or higher, a production method thereof, and an antioxidant for rubber using the phenylenediamine derivative as the effective constituent. [0002] Also, the present invention relates to an antioxidant for acrylic rubbers. More specifically, the present invention relates to an antioxidant for acrylic rubbers capable of giving an excellent heat aging resistance to an acrylic rubber vulcanization product by using two kinds of antioxidant compounds. BACKGROUND OF THE INVENTION [0003] In particular, requirements for high temperature resistant materials or for longer life materials has been desired in an automobile industry. In rubber-made mater...

Claims

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Application Information

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IPC IPC(8): C07C211/55C07C217/80C07C225/22C07C255/56C08K5/18
CPCC07C211/55C07C217/80C07C225/22C07C255/56C08K5/18C08L21/00
Inventor NAKAGOME, SEIJITODA, AKIHIKO
Owner NOK CORP
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