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Neodymium-Based Ziegler/Natta Catalysts and their Application in Diene Polymerization

  • Lars Friebe
  • Oskar Nuyken
  • Werner Obrecht
Part of the Advances in Polymer Science book series (POLYMER, volume 204)

Abstract

This article reviews the polymerization of dienes by neodymium (Nd) based Ziegler/Natta-catalyst systems. Special attention is paid to the monomer 1,3-butadiene (BD). The review covers scientific as well as patent literature which was published during the last decade to 2005. For a better understanding of the recent developments the early work on lanthanide-catalyzed diene polymerization is also addressed. The most important product obtained by Nd catalysis, butadiene rubber (Nd-BR) is introduced from an industrial as well as from a material scientist's point of view. Strong attention is paid to the great variety of Ziegler/Natta type Nd-catalyst systems which are often referred to as binary, ternary and quaternary systems. Different Nd-precursors, cocatalysts, halide donors and other additives are reviewed in detail. Technological aspects such as solvents, catalyst addition order, catalyst preformation, polymerization temperature, molar mass control, post-polymerization modifications etc., are presented. A considerable part of this review discusses variations of the molar ratios of the catalyst components and their influence on the polymerization characteristics. Non-established polymerization technologies such as polymerization in bulk, slurry and gas phase as well as the homopolymerization in the presence of other monomers are addressed. Also the copolymerizations of butadiene with isoprene, styrene and alkenes are reviewed. Mechanistic aspects such as formation of the active catalyst species, the living character of the polymerization, mode of monomer insertion, and molar mass control reactions are also explained. In the summary Nd technology is evaluated in comparison with other established technologies for the production of high cis-1,4-BR. Unsolved and open questions about Nd-catalyzed diene polymerization are also presented.

Diene polymerization Mechanism Neodymium catalysis Rubber Ziegler/Natta catalysts 

Abbreviations

6PPD

N-1,3-dimethylbutyl-N′-phenyl-p-phenylendiamine

7PPD

N-1,4-dimethylpentyl-N′-phenyl-p-phenylendiamine

77PD

N,N′-bis-1,4-(1,4-dimethylpentyl)-p-phenylendiamine

ABS

acrylonitrile butadiene styrene terpolymer

AFM

atomic force microscopy

at

atactic

BD

1,3-butadiene

BHT

2,6-di-tert-butyl-p-kresol

BIT

black incorporation time

BPH

2,2-methylene-bis-(4-methyl-6-tert-butylphenol)

BR

butadiene rubber

BuLi

butyl lithium

BzCl

benzyl chloride

ci

concentration of compound i

CL

ε-caprolactone

Co-BR

butadiene rubber obtained by cobalt catalysis

Cp

cyclopentadienyl

Cp*

pentamethylcyclopentadienyl

Cp*

C5Me4 n propyl ligand

d

day

D

electron donor

DEAC

diethylaluminum chloride

DEAH

diethylaluminum hydride

Di

didymium

DIBAC

diisobutylaluminum chloride

DIBAH

diisobutylaluminum hydride

DMDPS

dimethyl-di-2,4-pentadienyl-(E,E)-silane

DMF

N,N-dimethylformamide

DSC

differential scanning calorimetry

DSV

dilute solution viscosity

Ea

activation energy

EADC

ethylaluminum dichloride

EASC

ethylaluminum sesquichloride

E-BR

butadiene rubber produced by emulsion polymerization

EPDM

ethylene propylene diene copolymer-based rubber

EPM

ethylene propylene copolymer-based rubber

eq.

equivalents

GPC

gel permeation chromatography

h

hour

Hex

n-hexane or hexyl

HIBAO

hexaisobutyl alumoxane

HIPS

high-impact polystyrene

HMPTA

hexamethylphosphoric acid triamide

HV

versatic acid

IISRP

International Institute of Synthetic Rubber Producers

Ind

indenyl

IP

isoprene (2-methyl-1,3-butadiene)

IPPD

N-isopropyl-N′-phenyl-p-phenylendiamine

IR

isoprene rubber

it

isotactic

JSR

Japan Synthetic Rubber

ka

apparent rate constant

kp

polymerization rate constant

Li-BR

butadiene rubber obtained by alkyl lithium initiation

Ln

lanthanide

MAO

methylalumoxane

MCH

methyl cyclohexane

MDI

diphenylmethanediisocyanate

min

minute(s)

MMAO

modified methylalumoxane

MMD

molar mass distribution

Mn

number average molar mass

Mν

viscosity average molar mass

MU

Mooney units

Mw

weight average molar mass

NdA

neodymium(III) neopentanolate

Nd-BR

butadiene rubber obtained by neodymium catalysis

NdiO

neodymium(III) isooctanoate

NdO

neodymium(III) octanoate

NdN

neodymium(III) naphthenate

NdP

neodymium(III) bis(2-ethylhexyl)phosphate (Nd(P204)3)

NdV

neodymium(III) versatate

ni

molar amount of compound i

ni/nj

molar ratio of compound i and j

Ni-BR

butadiene rubber obtained by nickel catalysis

NR

natural rubber

PDI

polydispersity index M w/M n

pexp.

formal polymer chain number per Nd atom (determined experimentally)

ppm

parts per million

PSD

particle size distribution

ri

copolymerization parameter for monomer i

rp

polymerization rate

SBR

styrene butadiene rubber

SSC

single site catalyst

st

syndiotactic

St

styrene

T

temperature

TBB

tert-butyl benzene

TBP

tributyl phosphate

TEA

triethylaluminum

THF

tetrahydrofuran

TIBA

triisobutyl aluminum

TIBAO

tetraisobutylalumoxane

Ti-BR

butadiene rubber obtained by titanium catalysis

Tg

glass transition temperature

TMA

trimethylaluminum

TMEDA

tetramethyl ethylene diamine

TOF

turnover frequency

UCC

Union Carbide Corporation

VCH

vinyl cyclohexene

wt.%

weight percent

X

halide

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Notes

Acknowledgments

The authors thank Prof. Dr. Wieder, Dr. U. Wolf, Dr. H. Kloppenburg and Dr. S. Mücke for valuable advice and suggestions and J. C. Sauceda and D. E. Herbert for checking the manuscript. L. F. thanks Bayer AG for financial support during his diploma and Ph.D. thesis. L. F. also gratefully acknowledges a Postdoctoral Fellowship granted by the German Academic Exchange Service (Deutscher Akademischer Austauschdienst DAAD). L. F. thanks Prof. I. Manners for excellent working conditions in his group.

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Copyright information

© Springer-Verlag Berlin Heidelberg 2006

Authors and Affiliations

  1. 1.Department of ChemistryUniversity of TorontoTorontoCanada
  2. 2.Lehrstuhl für Makromolekulare StoffeTU MünchenGarchingGermany
  3. 3.Lanxess Deutschland GmbH, Business Unit TRP, LXS-TRP-APD-PDDormagenGermany

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