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 wherein R 1 is C1 to C4 linear alkyl, or C1 to C4 branched alkanediyl; X 1 , X 2 , X 3 are independently O, S, or a group of formula (II) or (III) where R 2 is C1 to C18 linear or branched alkyl; Z is R 3 , —OR 4 , or —R 5 —X 4 ; R 3 , R 4 are independently C1 to C18 linear or branched alkyl; R 5 is C1 to C18 alkanediyl or dialkyl ether diyl; X 4 is halogen or a group of structure IV, V, VI, VII or VIII wherein R 6 , R 7 , R 8 , R 9 , and R 10 are independently H or C1 to C8 alkyl; R 11 is C2 to C8 alkanediyl; R 12 and R 13 are independently H, aryl or C1 to C8 alkyl; Q is N or a group of structure IX wherein R 14 is C1 to C8 alkyl.
1. A functionalized elastomer comprising the reaction product of a living anionic elastomeric polymer and a polymerization terminator of formula I
wherein R 1 is C1 to C4 linear alkyl, or C1 to C4 branched alkanediyl;
in formula I X 1 , X 2 , X 3 are independently O, S, a group of formula II, or a group of formula III, with the proviso X 1 , X 2 , X 3 are O only if Z is —R 5 —X 4 where R 5 is C1 to C18 dialkyl ether diyl and X 4 is as defined below;
where R 2 is C1 to C18 linear or branched alkyl;
Z is R 3 , —OR 4 , or —R 5 —X 4 ; R 3 , R 4 are independently C1 to C18 linear or branched alkyl; R 5 is C1 to C18 alkanediyl or dialkyl ether diyl;
X 4 is halogen or a group of structure IV, V, VI, VII or VIII
wherein R 6 , R 7 , R 8 , R 9 , and R 10 are independently H or C1 to C8 alkyl; R 11 is C2 to C8 alkanediyl;
R 12 and R 13 are independently H, aryl or C1 to C8 alkyl; in formula V X 1 , X 2 , X 3 are independently O, S, or a group of formula II or III;
Q is N or a group of structure IX
wherein R 14 is C1 to C8 alkyl.
2. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from at least one diene monomer and optionally at least one vinyl aromatic monomer.
3. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from at least one of isoprene and butadiene, and optionally from styrene.
4. The functionalized elastomer of claim 1 , wherein the living anionic elastomer is derived from butadiene and styrene.
5. The functionalized elastomer of claim 1 , wherein the polymerization terminator of formula I is selected from the group consisting of the following structures
ETTS: 1-ethoxy-2,8,9-trithia-5-aza-1-silabicyclo[3.3.3]undecane; or 1-ethoxy-thiosilitrane
ETAS: 1-ethoxy-2,8,9-trimethyl-2,5,8,9-tetraaza-1-silabicyclo[3.3.3]undecane; or 1-ethoxy-2,8,9-triazasilatrane
EPTI: 3,7,10-trimethyl-1-(3-(oxiran-2-ylmethoxy)propyl)-2,8,9-trioxa-5-aza-1-silabicyclo[3.3.3]undecane; or 1-(3-(oxiran-2-ylmethoxy)propyl)-3,7,10-trimethylsilatrane.
6. A rubber composition comprising the functionalized elastomer of claim 1 .
7. The rubber composition of claim 6 , further comprising silica.
8. A pneumatic tire comprising the rubber composition of claim 7 .