Functionalized polymers

Patent metadata

Field	Value
Publication number	US-9315599-B2
Application number	US-201314144963-A
Country	US
Kind code	B2
Filing date	Dec 31, 2013
Priority date	Jan 2, 2013
Publication date	Apr 19, 2016
Grant date	Apr 19, 2016

Abstract

A method for preparing a functionalized polymer, the method comprising the steps of: (i) polymerizing monomer to form a reactive polymer, and (ii) reacting the reactive polymer with an azodiester.

First claim

What is claimed is:

1. A method for preparing a functionalized polymer, the method comprising the steps of:
(i) polymerizing monomer with a lanthanide-based catalyst to form a reactive polymer, and
(ii) reacting the reactive polymer with an azodiester.

2. The method of claim 1 , where the azodiester is defined by the formula I:

where R 1 and R 2 are each independently a monovalent organic group, and each α is independently an oxygen atom or a sulfur atom.

3. The method of claim 2 , where each α is an oxygen atom.

4. The method of claim 2 , where one or more α atoms are sulfur atoms.

5. The method of claim 2 , where each α is a sulfur atom.

6. The method of claim 2 , where the azodiester is defined by the formula II:

where R 2 is a monovalent organic group, R 3 , R 4 , and R 5 are each independently a hydrogen atom or a monovalent organic group, and each α is independently an oxygen atom or a sulfur atom.

7. The method of claim 2 , where the azodiester is defined by the formula III:

where R 3 , R 4 , R 5 , R 6 , R 7 , and R 8 are each independently a hydrogen atom or a monovalent organic group, and each α is independently an oxygen atom or a sulfur atom.

8. The method of claim 1 , where the azodiester is selected from the group consisting of dihydrocarbyl azodicarboxylates, bis(trihydrocarbylsilyl)azodicarboxylates, bis(dihydrocarbylhydrosilyl)azodicarboxylates, trihydrocarbylsilyl hydrocarbyl azodicarboxylates, dihydrocarbylhydrosilyl hydrocarbyl azodicarboxylates, dihydrocarbyl azothiodicarboxylates, bis(trihydrocarbylsilyl)azothiodicarboxylates, bis(dihydrocarbylhydrosilyl)azothiodicarboxylates, trihydrocarbylsilyl hydrocarbyl azothiodicarboxylates, and dihydrocarbylhydrosilyl hydrocarbyl azothiodicarboxylates.

9. The method of claim 1 , where the azodiester is a dihydrocarbyl azodicarboxylate selected from the group consisting of dimethyl azodicarboxylate, diethyl azodicarboxylate, di-n-propyl azodicarboxylate, diisopropyl azodicarboxylate, di-n-butyl azodicarboxylate, diisobutyl azodicarboxylate, di-t-butyl azodicarboxylate, di-n-pentyl azodicarboxylate, di-n-hexyl azodicarboxylate, di-n-heptyl azodicarboxylate, di-n-octyl azodicarboxylate, dicyclopentyl azodicarboxylate, dicyclohexyl azodicarboxylate, dibenzyl azodicarboxylate, diphenyl azodicarboxylate, di-o-tolyl azodicarboxylate, di-m-tolyl azodicarboxylate, di-p-tolyl azodicarboxylate, bis(2-ethylhexyl)azodicarboxylate, methyl ethyl azodicarboxylate, methyl n-propyl azodicarboxylate, ethyl n-propyl azodicarboxylate, methyl isopropyl azodicarboxylate, ethyl isopropyl azodicarboxylate, n-propyl isopropyl azodicarboxylate, methyl n-butyl azodicarboxylate, ethyl n-butyl azodicarboxylate, n-propyl n-butyl azodicarboxylate, isopropyl n-butyl azodicarboxylate, methyl isobutyl azodicarboxylate, ethyl isobutyl azodicarboxylate, n-propyl isobutyl azodicarboxylate, isopropyl isobutyl azodicarboxylate, n-butyl isobutyl azodicarboxylate, methyl t-butyl azodicarboxylate, ethyl t-butyl azodicarboxylate, n-propyl t-butyl azodicarboxylate, isopropyl t-butyl azodicarboxylate, n-butyl t-butyl azodicarboxylate, isobutyl t-butyl azodicarboxylate, methyl n-pentyl azodicarboxylate, ethyl n-pentyl azodicarboxylate, n-propyl n-pentyl azodicarboxylate, isopropyl n-pentyl azodicarboxylate, n-butyl n-pentyl azodicarboxylate, isobutyl n-pentyl azodicarboxylate, t-butyl n-pentyl azodicarboxylate, methyl n-hexyl azodicarboxylate, ethyl n-hexyl azodicarboxylate, n-propyl n-hexyl azodicarboxylate, isopropyl n-hexyl azodicarboxylate, n-butyl n-hexyl azodicarboxylate, isobutyl n-hexyl azodicarboxylate, t-butyl n-hexyl azodicarboxylate, n-pentyl n-hexyl azodicarboxylate, methyl n-heptyl azodicarboxylate, ethyl n-heptyl azodicarboxylate, n-propyl n-heptyl azodicarboxylate, isopropyl n-heptyl azodicarboxylate, n-butyl n-heptyl azodicarboxylate, isobutyl n-heptyl azodicarboxylate, t-butyl n-heptyl azodicarboxylate, n-pentyl n-heptyl azodicarboxylate, n-hexyl n-heptyl azodicarboxylate, methyl n-octyl azodicarboxylate, ethyl n-octyl azodicarboxylate, n-propyl n-octyl azodicarboxylate, isopropyl n-octyl azodicarboxylate, n-butyl n-octyl azodicarboxylate, isobutyl n-octyl azodicarboxylate, t-butyl n-octyl azodicarboxylate, n-pentyl n-octyl azodicarboxylate, n-hexyl n-octyl azodicarboxylate, n-heptyl n-octyl azodicarboxylate, methyl cyclopentyl azodicarboxylate, ethyl cyclopentyl azodicarboxylate, n-propyl cyclopentyl azodicarboxylate, isopropyl cyclopentyl azodicarboxylate, n-butyl cyclopentyl azodicarboxylate, isobutyl cyclopentyl azodicarboxylate, t-butyl cyclopentyl azodicarboxylate, n-pentyl cyclopentyl azodicarboxylate, n-hexyl cyclopentyl azodicarboxylate, n-heptyl cyclopentyl azodicarboxylate, n-octyl cyclopentyl azodicarboxylate, methyl cyclohexyl azodicarboxylate, ethyl cyclohexyl azodicarboxylate, n-propyl cyclohexyl azodicarboxylate, isopropyl cyclohexyl azodicarboxylate, n-butyl cyclohexyl azodicarboxylate, isobutyl cyclohexyl azodicarboxylate, t-butyl cyclohexyl azodicarboxylate, n-pentyl cyclohexyl azodicarboxylate, n-hexyl cyclohexyl azodicarboxylate, n-heptyl cyclohexyl azodicarboxylate, n-octyl cyclohexyl azodicarboxylate, cyclopentyl cyclohexyl azodicarboxylate, methyl benzyl azodicarboxylate, ethyl benzyl azodicarboxylate, n-propyl benzyl azodicarboxylate, isopropyl benzyl azodicarboxylate, n-butyl benzyl azodicarboxylate, isobutyl benzyl azodicarboxylate, t-butyl benzyl azodicarboxylate, n-pentyl benzyl azodicarboxylate, n-hexyl benzyl azodicarboxylate, n-heptyl benzyl azodicarboxylate, n-octyl benzyl azodicarboxylate, cyclopentyl benzyl azodicarboxylate, cyclohexyl benzyl azodicarboxylate, methyl phenyl azodicarboxylate, ethyl phenyl azodicarboxylate, n-propyl phenyl azodicarboxylate, isopropyl phenyl azodicarboxylate, n-butyl phenyl azodicarboxylate, isobutyl phenyl azodicarboxylate, t-butyl phenyl azodicarboxylate, n-pentyl phenyl azodicarboxylate, n-hexyl phenyl azodicarboxylate, n-heptyl phenyl azodicarboxylate, n-octyl phenyl azodicarboxylate, cyclopentyl phenyl azodicarboxylate, cyclohexyl phenyl azodicarboxylate, benzyl phenyl azodicarboxylate, methyl o-tolyl azodicarboxylate, ethyl o-tolyl azodicarboxylate, n-propyl o-tolyl azodicarboxylate, isopropyl o-tolyl azodicarboxylate, n-butyl o-tolyl azodicarboxylate, isobutyl o-tolyl azodicarboxylate, t-butyl o-tolyl azodicarboxylate, n-pentyl o-tolyl azodicarboxylate, n-hexyl o-tolyl azodicarboxylate, n-heptyl o-tolyl azodicarboxylate, n-octyl o-tolyl azodicarboxylate, cyclopentyl o-tolyl azodicarboxylate, cyclohexyl o-tolyl azodicarboxylate, benzyl o-tolyl azodicarboxylate, phenyl o-tolyl azodicarboxylate, methyl m-tolyl azodicarboxylate, ethyl m-tolyl azodicarboxylate, n-propyl m-tolyl azodicarboxylate, isopropyl m-tolyl azodicarboxylate, n-butyl m-tolyl azodicarboxylate, isobutyl m-tolyl azodicarboxylate, t-butyl m-tolyl azodicarboxylate, n-pentyl m-tolyl azodicarboxylate, n-hexyl m-tolyl azodicarboxylate, n-heptyl m-tolyl azodicarboxylate, n-octyl m-tolyl azodicarboxylate, cyclopentyl m-tolyl azodicarboxylate, cyclohexyl m-tolyl azodicarboxylate, benzyl m-tolyl azodicarboxylate, phenyl m-tolyl azodicarboxylate, o-tolyl m-tolyl azodicarboxylate, methyl p-tolyl azodicarboxylate, ethyl p-tolyl azodicarboxylate, n-propyl p-tolyl azodicarboxylate, isopropyl p-tolyl azodicarboxylate, n-butyl p-tolyl azodicarboxylate, isobutyl p-tolyl azodicarboxylate, t-butyl p-tolyl azodicarboxylate, n-pentyl p-tolyl azodicarboxylate, n-hexyl p-tolyl azodicar

Assignees

• Bridgestone Corp

Inventors

• Luo Steven
• Rademacher Christine

Classifications

• C08C19/25

  Incorporating silicon atoms into the molecule · CPC title

• C08F8/30

  Introducing nitrogen atoms or nitrogen-containing groups · CPC title

• C08C19/22

  Incorporating nitrogen atoms into the molecule · CPC title

• C08C19/44

  of polymers containing metal atoms exclusively at one or both ends of the skeleton · CPC title

• C08F36/06 Primary

  Butadiene · CPC title