US 2018/0002490 A1 · Terminal-Functionalized Polymer And Related Methods

Abstract

Disclosed herein are terminal-functionalized polymers functionalized with silicon-containing functionalizing agents, rubber compositions including the polymers, methods for improving the cold flow resistance of a polymer, methods for improving the filler dispersion of a silica-filled rubber composition, and processes for preparing the terminal-functionalized polymer.

Claims21

Dependent claims

1-20. (canceled)

A terminal-functionalized polymer having the following structure (I), (II), or (III) as follows:

wherein for formulas (I), (II) and (III), P is a polymer chain comprising at least one type of conjugated-diene monomer;
for formula (I) x, y and z are integers, where z does not equal 0, either x or y, but not both can be 0, and x+y+z≧8;
R1, R2 and R3 are the same or different and are selected from the group consisting of:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl or cycloalkoxy groups having 3 to 20 carbons,
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons, and
(iv) R5X, where X is selected from Cl, Br, SdR6, NR62, OR6, SCOR6, CO2R6, olefins, amino groups and vinyl-containing groups, wherein d=1 to 10, R5 is selected from alkylene groups having 1 to 20 carbons, cycloalkylene groups having 3 to 20 carbons, R4 and R6 are selected from alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, and alkylaryl groups having 7 to 20 carbons, and M is selected from H or a metal;
for formula (II), Ra and Rc are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and vinyl-containing groups of the foregoing,
Rb is selected from:
(i) an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and
n is 2 to 20;
and
for formula (III), Ra, Rb, Rc and Rd are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons,
Re is independently selected from:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and m is 1 to 20.

18 more elements

A process for preparing a terminal-functionalized polymer, the process comprising

reacting the live end of a conjugated diene monomer-containing polymer chain with a functionalizing agent comprising:
(a) a polysilsesquioxane having at least 8 Si with each Si bonded to three O and each Si also bonded to one of R1, R2, R3, where R1, R2, and R3 are the same or different and are selected from the group consisting of:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons,
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons, and
(iv) R5X, where X is selected from Cl, Br, SdR6, NR62, OR6, SCOR6, CO2R6, olefins, amino groups and vinyl-containing groups, wherein d=2 to 8, R5 is selected from alkylene groups having 1 to 20 carbons, cycloalkylene groups having 3 to 20 carbons, and and R5 are independently selected from alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, and alkylaryl groups having 7 to 20 carbons,
or
(b) a compound having the following structure (IV) or (V)
where for formula (IV) Ra and Rc are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and vinyl-containing groups of the foregoing;
Rb and Rd are the same or different and each is selected from:
(i) an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
n is 2 to 20;
and
where for formula (V) Ra, each Rb, Rc and Rd are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and
Re is selected from:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and
m is 1 to 20.

19 more elements

Dependencies are inferred from the claim text.

Facts

Application

15/540,833Filed 22 Dec 2015

Priority

30 Dec 2014

Published

4 Jan 2018

Term ends

Not estimatedThe source records don’t support an estimate.

Classification8 codes

C08G 77/442
Block-or graft-polymers containing polysiloxane sequences: containing vinyl polymer sequences
C08L 83/10
Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with…
C08F 230/085
Containing silicon: the monomer being a polymerisable silane, e.g. acryloyloxy trialkoxy silanes or vinyl trialkoxysilanes
Y02T 10/86
Technologies aiming to reduce greenhouse gasses emissions common to all road transportation technologies: optimisation of rolling resistance, e.g.…

Abstract

Claims21

Dependent claims

1-20. (canceled)

A terminal-functionalized polymer having the following structure (I), (II), or (III) as follows:

wherein for formulas (I), (II) and (III), P is a polymer chain comprising at least one type of conjugated-diene monomer;
for formula (I) x, y and z are integers, where z does not equal 0, either x or y, but not both can be 0, and x+y+z≧8;
R1, R2 and R3 are the same or different and are selected from the group consisting of:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl or cycloalkoxy groups having 3 to 20 carbons,
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons, and
(iv) R5X, where X is selected from Cl, Br, SdR6, NR62, OR6, SCOR6, CO2R6, olefins, amino groups and vinyl-containing groups, wherein d=1 to 10, R5 is selected from alkylene groups having 1 to 20 carbons, cycloalkylene groups having 3 to 20 carbons, R4 and R6 are selected from alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, and alkylaryl groups having 7 to 20 carbons, and M is selected from H or a metal;
for formula (II), Ra and Rc are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and vinyl-containing groups of the foregoing,
Rb is selected from:
(i) an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and
n is 2 to 20;
and
for formula (III), Ra, Rb, Rc and Rd are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons,
Re is independently selected from:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and m is 1 to 20.

18 more elements

A process for preparing a terminal-functionalized polymer, the process comprising

reacting the live end of a conjugated diene monomer-containing polymer chain with a functionalizing agent comprising:
(a) a polysilsesquioxane having at least 8 Si with each Si bonded to three O and each Si also bonded to one of R1, R2, R3, where R1, R2, and R3 are the same or different and are selected from the group consisting of:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons,
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons, and
(iv) R5X, where X is selected from Cl, Br, SdR6, NR62, OR6, SCOR6, CO2R6, olefins, amino groups and vinyl-containing groups, wherein d=2 to 8, R5 is selected from alkylene groups having 1 to 20 carbons, cycloalkylene groups having 3 to 20 carbons, and and R5 are independently selected from alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, and alkylaryl groups having 7 to 20 carbons,
or
(b) a compound having the following structure (IV) or (V)
where for formula (IV) Ra and Rc are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and vinyl-containing groups of the foregoing;
Rb and Rd are the same or different and each is selected from:
(i) an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
n is 2 to 20;
and
where for formula (V) Ra, each Rb, Rc and Rd are the same or different and each is independently selected from H, alkyl groups having 1 to 20 carbons, cycloalkyl groups having 3 to 20 carbons, alkylaryl groups having 7 to 20 carbons, and
Re is selected from:
(i) H, an alkyl group having 1 to 20 carbons, or an alkoxy group having 1 to 20 carbons,
(ii) cycloalkyl group or cycloalkoxy groups having 3 to 20 carbons, and
(iii) alkylaryl or alkaryloxy groups having 7 to 20 carbons;
and
m is 1 to 20.

19 more elements

Dependencies are inferred from the claim text.

Terminal-Functionalized Polymer And Related Methods

Life of this patent

Abstract

Claims21

Terminal-Functionalized Polymer And Related Methods

Life of this patent

Abstract

Claims21