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Resorcinolic derivative for rubber compounds

a technology of resorcinolic compounds and rubber, applied in the field of resorcinolic compounds for rubber reinforcement, can solve the problems of suggesting the use of 3-hydroxydiphenylamine as a rubber reinforcement compound, and achieve the effect of improving physical and mechanical properties

Inactive Publication Date: 2011-02-01
SUMIKA ELECTRONICS MATERIALS INC USA D B A SUMITOMO CHEM ADVANCED TECH INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

Benefits of technology

[0012]The present invention provides for the use of 3-hydroxydiphenylamine (“3-HDPA”) in place of resorcinol to enhance the physical and mechanical properties of both uncured and cured rubber compounds. Several advantages are realized by using 3-HDPA as a methylene acceptor. For example, 3-HDPA has a lower melting point than resorcinol; this means the compound has better dispersibility or mixing with rubber compounds at a lower temperature. Because of its high molecular weight, 3-HDPA has a lower volatility than resorcinol. While 3-HDPA has the same number of reactive sites as resorcinol, it has a higher reactivity, due to its being an m-aminophenol-type derivative.
[0014]One aspect of the present invention to provide rubber compounds having enhanced physical and mechanical properties in both their cured and uncured forms.
[0015]It is a further aspect of the invention to provide a method for making rubber compounds having improved physical and mechanical properties.

Problems solved by technology

Neither of these patents teach or suggest the use of 3-hydroxydiphenylamine as a rubber-reinforcing compound, however.

Method used

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  • Resorcinolic derivative for rubber compounds
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  • Resorcinolic derivative for rubber compounds

Examples

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examples

[0029]The following examples are intended to illustrate the invention and should not be construed as limiting the invention in any way.

example no.1

Example No. 1

[0030]Into a 500-ml round bottomed flask equipped with a mechanical stirrer, thermometer and Dean-Stark condenser was charged 0.5 mole (55.0 grams) of resorcinol, 1.5 mole (139.7 grams) of aniline and 2.2 grams of PTSA catalyst. The reaction mixture was heated to between 185-205° C.; about 11.0 grams of distillate was collected in the Dean-Stark trap in about 10.0 hours. After this, 1.0 gram of 50% wt. / wt. aqueous NaOH solution was added to neutralize the catalyst. Then, vacuum was applied to distill out the excess aniline under 28″ of Hg and 160-165° C. temperature conditions. The final reaction product weighed 91.9 grams and showed the following composition determined by LC / GC analysis.

[0031]

Composition (wt. %)Aniline5.7Resorcinol6.73-Hydroxydiphenylamine89.0Impurity (unknown)2.3

[0032]The melting point as determined by the capillary method was between about 65-70° C.

[0033]The above crude reaction product was recrystallized from an aqueous solution. The purified materi...

example no.2

Example No. 2

[0035]The procedure described in Example No. 1 was repeated with 1.5 moles of resorcinol, 2.25 moles of aniline and 6.0 grams of PTSA catalyst. Continuous passage of nitrogen gas was done to remove the water by-product formed during the reaction. The reaction took about 21.0 hours to remove 27.1 grams of water distillate. The product weighed 280.0 grams after distilling out the excess aniline. The melting point was determined to be between 68-72° C. The chemical composition determined by the LC / GC analysis showed the presence of aniline=2.6 wt. %, resorcinol=0.6 wt. % and unknown impurities=4.0 wt. %

[0036]Further purification of this crude material by an aqueous recrystallization method showed that the 3-hydroxydiphenylamine had a melting point of 71-75° C. and contained the following impurities (wt. %).

[0037]

Aniline0.07Resorcinol0.04Unknown4.6

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Abstract

A vulcanizable rubber composition and method for making the same are disclosed. The rubber composition comprises a rubber component mixed with a methylene donor and methylene acceptor; the methylene acceptor is 3-hydroxydiphenylamine.

Description

FIELD OF THE INVENTION[0001]The present invention relates to resorcinolic compounds for rubber reinforcement. More particularly, the invention relates to resorcinolic derivatives that can be substituted for resorcinol during rubber manufacture; use of the present resorcinolic compounds results in enhanced cure and mechanical properties of the cured rubber compound as compared with resorcinol, while maintaining the favorable properties of uncured rubber compounds achieved when resorcinol is used.BACKGROUND OF THE INVENTION[0002]Resorcinol, resorcinolic derivatives and resorcinol-formaldehyde resins have been used in the rubber industry as rubber compounds and adhesives. These resorcinolic compounds are unique materials in rubber compounding, since they act as thermosetting and vulcanizing plasticizers. They are very efficient plasticizers for rubber during the processing operations. The use of these compounds allows easier processing, higher loading and excellent extrusions of the ru...

Claims

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Application Information

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IPC IPC(8): C08K5/17C07C215/76C08K5/13C08K5/18C08K5/3477C08L21/00
CPCC08K5/13C08K5/18C08K5/3477C08L21/00C08K5/29
Inventor DURAIRAJ, RAJ B.PETERSON, JR., ALEX
Owner SUMIKA ELECTRONICS MATERIALS INC USA D B A SUMITOMO CHEM ADVANCED TECH INC
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