The Goodyear & Tire Rubber Company

Ji Yang Jin

Frank James Feher

Aaron Patrick Murray

Kelsey Elizabeth Cantwell

Thomas Franklin Spilker

The present invention provides a route for synthesizing monofunctional thiuram compounds that is safe, environmentally friendly, and cost effective. This method specifically involves synthesizing a monofunctional thiuram by (1) reacting a tetraorganylthiuram disulfide with an organyl mercaptan to produce the monofunctional thiuram and a dithiocarbamate metal salt or a dithiocarbamate metalloid salt under basic conditions, (2) separating the monofunctional thiuram in an organic phase from the dithiocarbamate metal salt or the dithiocarbamate metalloid salt in an aqueous phase, and (3) recovering the monofunctional thiuram from the aqueous phase. The monofunctional thiuram compounds made in accordance with this invention are of particular value as accelerators for use in the vulcanization of rubber. The use of these monofunctional thiuram compounds as accelerators provides good cure rates and as well as good scorch safety.

Synthesis of monofunctional thiuram accelerator

The present invention is directed to a functionalized elastomer comprising the reaction product of a living anionic elastomeric polymer and a polymerization terminator of formula I where X is Cl, Br, or I;m is an integer from 0 to 2, n is an integer from 1 to 3, with the proviso that n+m=3;R, Rare independently C1 to C18 alkyl, aryl, or a combination thereof, or R, Rare independently &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, or Rand Rtaken together with their common nitrogen atom and optionally a sulfur or oxygen heteroatom to form a five to eight membered ring;Ris hydrogen, or C1 to C18 alkyl, aryl, or a combination thereof, or Ris &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, or Ris -R-R, where Ris C1 to C3 alkanediyl and Ris selected from the following structures&#x2014;S&#x2014;Z, &#x2014;N(R)(R), &#x2014;O(Y), or Si(OR), where Rand Rare independently C1 to C18 alkyl, aryl, or a combination thereof,Y and Z are independently selected from the group consisting of methoxymethyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuranyl, tert-butyl, allyl, 1-ethoxyethyl, benzyl, triphenylmethyl, triethylsilyl, triisopropylsilyl, trimethylsilyl, tert-butyl dimethyl silyl, tert-butyl diphenyl silyl, and isopropyldimethylsilyl, andRare independently C1 to C4 alkyl;or when m=1, the polymerization terminator may have the formula II where R, Rare independently C1 to C18 alkyl, aryl, or a combination thereof, or R, Rare independently &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, X and Rare as defined previously, and k is an integer from 0 to 10.

Functionalized polymer, rubber composition and pneumatic tire

The present invention is directed to a functionalized elastomer comprising the reaction product of a living anionic elastomeric polymer and a polymerization terminator of formula I where X is Cl, Br, or I;m is an integer from 0 to 2, n is an integer from 1 to 3, with the proviso that n+m=3;R, Rare independently C1 to C18 alkyl, aryl, or a combination thereof, or R, Rare independently &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, or Rand Rtaken together with their common nitrogen atom and optionally a sulfur or oxygen heteroatom to form a five to eight membered ring;Ris hydrogen, or C1 to C18 alkyl, aryl, or a combination thereof, or Ris &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, or Ris &#x2014;R&#x2014;R, where Ris C1 to C3 alkanediyl and Ris selected from the following structures&#x2014;S&#x2014;Z, &#x2014;N(R)(R), &#x2014;O(Y), or Si(OR), where Rand Rare independently C1 to C18 alkyl, aryl, or a combination thereof,Y and Z are independently selected from the group consisting of methoxymethyl, tetrahydropyranyl, tetrahydrothiopyranyl, tetrahydrofuranyl, tert-butyl, allyl, 1-ethoxyethyl, benzyl, triphenylmethyl, triethylsilyl, triisopropylsilyl, trimethylsilyl, tert-butyl dimethyl silyl, tert-butyl diphenyl silyl, and isopropyldimethylsilyl, andRare independently C1 to C4 alkyl;or when m=1, the polymerization terminator may have the formula II where R, Rare independently C1 to C18 alkyl, aryl, or a combination thereof, or R, Rare independently &#x2014;SiRwhere R is independently alkyl, aryl, alkoxy, or disubstituted amino, X and Rare as defined previously, and k is an integer from 0 to 10.

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Akron, OH, United States of America

Ji Yang Jin