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Polymeric Betaines: Synthesis, Characterization, and Application

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Supramolecular Polymers Polymeric Betains Oligomers

Part of the book series: Advances in Polymer Science ((POLYMER,volume 201))

Abstract

This review summarizes mostly the literature data accumulated during the last decade on betaine-type polyampholytes. Synthetic pathways to polybetaines consisting of radical polymerization, the Michael addition reaction, and polymer-analogous transformation are discussed together with methods of controlled polymerization, such as group transfer polymerization, atomic transfer radical polymerization, and reversible addition fragmentation transfer. The role of intra- and interchain associates resulting in insolubility in pure water due to the formation of ionically cross-linked network structures, and solubility in saline water because of the disruption of the ionic networks, are outlined. Attention is also paid to the recent advancement of hydrophobically modified polymeric betaines with emphasis on phospholipid-containing vinyl polymers. Polymer complexes of polybetaines, in particular interpolyelectrolyte, polymer–surfactant, and polymer–metal complexes, are considered in the light of the competition between intra- and intermolecular ionic contacts and the cooperative character of interactions. Stimuli-sensitive behavior and morphological changes of polybetaine hydrogels triggered by changes of the pH, ionic strength, water–organic solvent mixture, metal complexation, and DC electric field are discussed with respect to the ionization state of the macromolecules and the thermodynamic quality of solvents, as well as osmotic, chelating, and polarization effects. Some application aspects of polybetaines in medicine, biotechnology, hydrometallurgy, and the oil industry are also discussed.

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Abbreviations

AMBNa:

Sodium 3-acrylamido-3-methylbutanoate

AMPDAPS:

3-[(2-Acrylamido-2-methylpropyl)dimethylammonio]-1-propanesulfonate

APDAPS:

3-[N-(3-Acrylamido)propyl-N,N′-dimethylammonio]-propanesulfonate

APDMAE:

2-(3-Acrylamidopropyldimethylammonio)-ethanoate

APE:

Anionic polyelectrolyte

ATRP:

Atom transfer radical polymerization

BMA:

n-Butyl methacrylate

BSA:

Bovine serum albumin

Chol:

Cholesterol

CPE:

Cationic polyelectrolyte

CRP:

Controlled radical polymerization

CTA:

Chain transfer agent

DADMAC:

N,N-Diallyl-N,N-dimethylammonium chloride

DC:

Direct current

DEAEM:

2-(Diethylamino)ethyl methacrylate

DIPAEM:

2-(Diisopropylamino)ethyl methacrylate

DLS:

Dynamic light scattering

DMAAPS:

N,N-Dimethyl(acrylamidopropyl)ammonium propanesulfonate

DMAEM:

N,N-Dimethylaminoethyl methacrylate

DMAPS:

N,N-Dimethyl-N-(2-methacryloyloxyethyl)ammonium propanesulfonate

DMF:

Dimethylformamide

DMSO:

Dimethyl sulfoxide

DNA:

Deoxyribonucleic acid

EDMA:

Ethylene dimethacrylate

EDTA:

N,N-Ethylenediaminetetraacetic acid

ELISA:

Enzyme-linked immunosorbent assay

GPC:

Gel-permeation chromatography

GTP:

Group transfer polymerization

HPLC:

High-performance liquid chromatography

IEP:

Isoelectric point

IPC:

Interpolyelectrolyte complexes

LB:

Langmuir–Blodgett

LCST:

Lower critical solution temperature

MAA:

Methacrylic acid

MEMA:

2-(N-Morpholino)ethyl methacrylate

MPC:

2-Methacryloyloxyethyl phosphorylcholine

NaPSS:

Poly(styrenesulfonate sodium salt)

NIPAM:

N-Isopropylacrylamide

PAA:

Poly(acrylic acid)

PAAm:

Polyacrylamide

PAESD:

Poly(diallylaminoethanoate-co-sulfur dioxide)

PAMPS:

Poly(2-acrylamido-2-methylpropanesulfonic acid)

PBA:

Poly(butyl methacrylate)

PCB:

Polycarbobetaine

PCEAC:

Poly(carboxyethyl 3-aminocrotonate)

PCEAC-Ala:

Poly(carboxyethyl 3-aminocrotonate) modified by β-alanine

PCEAC-Ea:

Poly(carboxyethyl 3-aminocrotonate) modified by ethanolamine

PCEAC-Gly:

Poly(carboxyethyl 3-aminocrotonate) modified by glycine

PCEAC-Lys:

Poly(carboxyethyl 3-aminocrotonate) modified by lysine

PCECHAC:

Poly(carboxyethyl 3-cyclohexylaminocrotonate)

PCEPAC:

Poly(carboxyethyl 3-propylaminocrotonate)

PCMEDDAC:

Poly3-[(2-carboxy-1-methylethyl)dodecylaminocrotonate]

PDADMAC:

Poly(N,N-diallyl-N,N-dimethylammonium chloride)

PDI:

Polydispersity index

PDMAPAA-Q:

Quaternized polyN-[3-(dimethylamino)propyl]acrylamide chloride

PDMAPS:

Poly[3-dimethyl(methacryloyloxyethyl)ammonium propanesulfonate]

PEG:

Poly(ethylene glycol)

PEI:

Polyethyleneimine

PEO:

Poly(ethylene oxide)

PHMG:

Poly(hexamethylene guanidine)

PMAA:

Poly(methacrylic acid)

PMMA:

Poly(methyl methacrylate)

PNIPAM-PC:

Phosphorylcholine-based poly-N-isopropylacrylamide

polyAMPS:

poly(2-acrylamido-2-methylpropanesulfonic acid)

polyCEACPhos:

Poly(carboxyethyl 3-aminocrotonate) modified by phosphatidylethanolamine

polyTRIM:

Poly(trimethylpropane trimethacrylate)

PPD:

Pour point depressant

PPO:

Poly(propylene oxide)

PSB:

Polysulfobetaine

PVA:

Poly(vinyl alcohol)

PVP:

Poly(N-vinylpyrrolidone)

RAFT:

Reversible addition fragmentation chain transfer

UCST:

Upper critical solution temperature

VPPS:

2-Vinylpyridiniopropanesulfonate

XPS:

X-ray photoelectron spectroscopy

ZPE:

Zwitterionic polyelectrolyte

a :

Exponent of Mark–Kuhn–Houwink equation

A 2 :

Second virial coefficient

α:

Ionization degree

αe :

Electrostatic expansion factor

C protein :

Protein concentration

C s :

Low molecular weight salt concentration

d h :

Hydrodynamic diameter

E :

Voltage

E A :

Activation energy

[η]:

Intrinsic viscosity

ηsp/C :

Reduced viscosity

G el :

Electrostatic Gibbs energy

I E :

Fluorescence intensity of excimer

I M :

Fluorescence intensity of monomer

k i :

(i = 1, 2, 3, …) Microscopic ionization constant

K i :

(i = 1, 2, 3, …) Macroscopic ionization constant

K t :

Tautomeric constant

L :

Distance

M n :

Number average molecular weight

M w :

Weight average molecular weight

μ:

Ionic strength of the solution

pK a :

Ionization constant of acidic group

pK b :

Ionization constant of basic group

pHc :

Boundary between the primary and nonassociative phases

pHiep :

Isoelectric pH

pHϕ :

Boundary between the primary and aggregate phases

R :

Molar ratio of polyelectrolyte/polybetaine

R g :

Radius of gyration

R h :

Hydrodynamic radius

R p :

Propagation rate

t :

Time

T g :

Glass transition temperature

Z pr :

Protein charge

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Acknowledgments

Financial support from INTAS-00/57, INTAS-00/113, and INTAS-Aral 1033 grants is greatly acknowledged.

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Authors and Affiliations

  1. Institute of Polymer Materials and Technology, Satpaev Str. 18a, 050013, Almaty, Republic of Kazakhstan

    Sarkyt Kudaibergenov

  2. Fraunhofer-Institute for Applied Polymer Research, Geiselbergstrasse 69, 14476, Potsdam-Golm, Germany

    Werner Jaeger & Andre Laschewsky

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  1. Sarkyt Kudaibergenov
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Correspondence to Sarkyt Kudaibergenov .

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Kudaibergenov, S., Jaeger, W., Laschewsky, A. (2006 ). Polymeric Betaines: Synthesis, Characterization, and Application. In: Supramolecular Polymers Polymeric Betains Oligomers. Advances in Polymer Science, vol 201. Springer, Berlin, Heidelberg. https://doi.org/10.1007/12_078

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