Contents

Preface - 3rd Edition

Preface - 2nd Edition

Preface - Book Series

Literature/Trademarks/Other

Introduction

Abbreviations

Terms and Definitions

1 Chemistry/Polymer Chemistry

2 Radiometry

Resin Materials in Dentistry

1 Introduction

2 Modern Dental Resins

Matrix Resins

1 Introduction

2 Functional Groups and Monomer Links

3 Polyreactions

3.1 Polymerization

3.1.1 Free Radical Polymerization

3.1.2 Cationic Polymerization

3.1.3 Anionic Polymerization

3.1.4 Ring-Opening Polymerization

3.1.5 Technical Polymerization Processes

3.2 Polycondensation

3.3 Polyaddition

4 Matrix Resins According to Links

4.1 Introduction

4.2 Carbon-Carbon Link

4.3 Ester Link

4.4 Amide Link

4.5 Urethane Link

4.6 Ether Link

4.7 Siloxane Link

4.8 Sulfone Link

5 Structures and Properties of Monomers and Oligomers

6 Structures and Properties of Polymers

6.1 Introduction

6.2 Thermoplastics

6.3 Elastomers

6.4 Duromers

6.5 Interpenetrating Polymer Networks

Initiators and Catalysts

1 Introduction

2 Initiators

2.1 Thermal/Heat Initiators

2.2 Redox Initiators

2.3 Photoinitiators

2.3.1 Radical Photoinitiators

2.3.2 Cationic Photoinitiators

3 Catalysts

Fillers

1 Introduction

2 Organic Fillers

3 Inorganic Fillers

4 Surface Treatment of Fillers

Pigments and Dyes

1 Introduction

2 Pigments

3 Dyes

Additives

1 Introduction

2 Stabilizers

3 Antioxidants

4 UV-Stabilizers

5 Plasticizers

Physical and Chemical Properties

1 Introduction

2 Physical Properties

3 Chemical Properties

4 Ageing Processes/Depolymerization

Material Testing/Standards

1 Introduction

2 Material Testing

3 Standards

Toxicology/Clinics/Standards

1 Introduction

2 Toxicology

3 Standards Laboratory Testing

4 Standards Clinical Testing

Denture Base Resins

1 Introduction

2 Classification

3 Processing Methods

3.1 Full and Partial Embedment

3.2 No Embedment

3.3 Insulation of Plaster

4 Polymethyl (meth)acrylates

4.1 1 Powder/Liquid Systems - Formulation

4.2 Powder/Liquid Products - Processing

4.3 Polymerizable One Component Products - Processing

5 Other Denture Base Resins - Formulation, Processing

Resin Teeth

1 Introduction

2 Formulation, Production and Processing

Denture Reline Resins

Crown and Bridge Veneer Resins

1 Introduction

2 Classification, Formulation and Processing

Resins for Provisional Crowns and Bridges

Resins for Crown and Bridge Frames

Impression Materials

1 Introduction

2 Classification, Formulation and Processing

2.1 Polysulfides

2.2 Polyethers

2.3 Polysiloxanes

2.3.1 Condensation Polysiloxanes

2.3.2 Addition Polysiloxanes

Resin Based Filling Composites

1 Introduction

2 Classification

3 Formulation

3.1 Microfill Filling Composites

3.2 Hybrid/Micro-Hybrid Filling Composites

3.3 Compomer Filling Composites

3.4 Ormocer Filling Composites

3.5 Nanoparticle Filling Composites

3.6 Silorane Filling Composites

3.7 Bulk-Fill Filling Composites

3.8 Giomer Filling Composites

3.9 Other Resin Composites

Resin Based Luting Composites

Enamel/Dentin Adhesives

1 Introduction

2 Classification of Enamel/Dentin Adhesives

3 Formulation and Properties

Other Dental Polymers

Light-Curing Devices

CAD/CAM Technology

1 Introduction

2 Intraoral Scanning

3 Grinding and Milling

4 3D-Printing

Curriculum Vitae

Literature

Index

Preface - 3rd Edition

Mistakes and errors of the 2nd Edition were corrected and several chapters, figures and tables were improved and updated.

Best regards

Ralf

March 2021

Preface - 2nd Edition

Mistakes and errors of the 1st Edition have been corrected and some illustrations have been improved. The complete structure of the book has been revised and optimized. But also several chapters were supplemented by new information. A complete new chapter about CAD/CAM technology is added.

Best regards

Ralf

January 2020

Preface - Book Series

Resin materials are broadly used in dentistry for almost all indications and they will gain even more importance in future. Especially the increasing performance and efficiency of CAD/CAM technology and 3D-printing open possibilities to use resins not used up to now for dental applications. Besides of dentists, dental technicians, dental students, teachers of dental universities/schools, postgraduate students and PhD candidates there are many other specialists such as researchers, material scientists, industrial developers or experts of adjoining professional disciplines who are technically engaged in dental resins. Mainly two reasons are responsible for this interest: a) many persons dealing with dentistry feel a large desire for deeper knowledge in dental resins, b) the knowledge of many different specialists is requested to develop, to investigate, to test and to evaluate dental resins; c) dental resins offer very sophisticated highly developed properties so that they are also used in other disciplines for other purposes or are the base to develop tailor-made products for other very special non-dental applications.

The idea of this e-Book is to present a three-level textbook dealing with material science and technology of dental resins. The Basic Level addresses students, dental technicians, teachers or all those interested in dental resins. The Basic Level gives a comprehensive insight into chemistry, physics and toxicology of dental resins and their technical application. The Advanced Level broadens the information of the Basic Level significantly and mainly addresses teachers of dental universities/schools, postgraduate students, PhD candidates, researchers, material scientists, industrial developers or experts of adjoining professional disciplines. The Expert Level gives a very deep insight into the science of dental resins and mainly addresses scientists doing research on dental resins, industrial developers or scientists of adjoining professional disciplines who are very strongly interested to become also specialists in dental resin material science.

Contrarily to print books, it is the great advantage of e-Books that improvements, corrections, additions or enhancements can be done swiftly so that new improved editions can be produced and distributed rapidly and cheaply. Therefore, the e-Book is the ideal format to update the content immediately whenever errors or mistakes must be eliminated or the scientific progress makes it necessary. It is the desired and planned scenario that the content of this e-Book will not become obsolete as fast as it usually happens with conventional print books but will be refreshed in shorter periods of time.

Illustrations and tables will increase in number with each level. The information they give is - hopefully - clear and understandable but certainly they will not become prettier or colored. This is a low-cost book and everything is done keeping costs to a minimum.

The author is aware that there will be errors, inaccuracies and ambiguousness but hopefully no incorrect or even misleading information in the text despite of all the care taken. The honorable readership is kindly asked for understanding and the author will be very grateful for any hints and proposals to improve the content of the book or the book at all. Therefore, every type of constructive criticism will be highly appreciated.

Having said all this, I hope you will enjoy the book and you will get the information that is helpful and valuable for you and your work.

Many thanks and best regards

Ralf

Literature/Trademarks/Other

Not all the literature used to write this book is specifically cited. Common dental, chemical or material science knowledge taken from textbooks is not specifically cited in the text. Such textbooks are

- dentistry and dental materials [1-20]

- chemistry [21-46]

- adhesives and adhesive technology [47-50]

- material science [50-52]

Also information, figures or tables taken from the author’s sole publications are not specifically cited; these are [53-79].

Information (terms, definitions, etc.) deriving from scientific organizations is not always specifically cited; these organizations are [80-83].

Specific information given is specifically cited.

Product names are not specifically marked as registered even if they are so. Principally brand names are only used when they are important in connection with the described subjects. This might be the case when only one product of a specific product category is available. Apart from that representatives of product categories presented in tables or graphics are anonymized.

Numbers of figures and tables indexed with “b” are part of the basic, advanced and expert level version. When they are indexed with “a” they are part of the advanced and expert level and when they are indexed “e” they are only part of the expert level version. In higher versions improved figures or tables of lower versions are indexed with “ba”, “ac” or “bac”.

Introduction

Besides of metals, alloys and ceramics plastics and composite resins have become to one of the most important material category in all areas of daily life such as engineering, electronics, building and construction industry, car industry and many other industries as well as in medicine and dentistry. In 1922 Hermann Staudinger discovered these high molecular compounds and called them macromolecules [84]. This was the start of a new until then unknown chemistry called polymer chemistry. The development of numerous polymeric materials and combinations thereof with other organic or inorganic substances or materials gave birth to a huge number of advanced materials with exceptional properties.

In the early years plastics were considered to be cheap and inferior materials but today composite resins and high performance plastics are very valuable and indispensable in all industries. The most important aspect for the resin materials’ breakthrough is certainly the fact that for nearly every usage custom-made, often also called tailor-made, products can be developed and finally provided. For sure, more and more new, until now unknown, resins or resin composites will be tailor-made for further or today even unknown applications in future.

Resin materials (plastics, composite plastics, composite resins, resin composites) are high molecular mass products (polymers). They are manufactured by transformation of naturally occurring or by synthesis from low molecular mass substances (monomers). These low molecular mass substances (monomers) are the smallest multiple recurring units building the high molecular mass substances (polymers). The properties of each of the resulting polymers depend on how the monomers are linked, on their chemical structure as well as on the spatial configuration of the formed macromolecules. Polymers or macromolecules do not have an exact but an average molecular mass because the single chains building the polymer/macromolecule are growing randomly and not in a well-defined manner.

Abbreviations

Abbreviations important in the context of this book or the dental literature are given in accordance with IUPAC [80-83]. Information given here is important for all versions of this book series.

Monomers

4-Met = 4-methacryloyloxypropyl trimellitic acid

4-Meta = 4-methacryloyloxypropyl trimellitic anhydride

AA = acrylic acid

BDMA = butanediol dimethacrylates

Bis-EDMA(2) = bis-EMA(2) = 2,2-bis[4(3'-methacryloyloxy)ethoxyphenyl)]propane

Bis-GMA = 2,2-bis[4(3'-methacryloyloxy-2'-hydroxy)propoxyphenyl]propane

EDMA = ethylene glycol dimethacrylate

EMA = ethyl methacrylate

GDM = glycerol dimethacrylate

GPDM = glycerol phosphate dimethacrylates

HEMA = hydroxyethyl methacrylate

HPMA = hydroxypropyl methacrylate

i-BuMA = iso-butyl methacrylate

MA = methyl acrylate

MDP = 10-methacryloyloxydecyl dihydrogen phosphate

MMA = methyl methacrylate

PENTA = dipentaerythritol pentaacrylate monophosphate

PMDM = pyromellitic dihydroxethyl methacrylate

TEGDMA = triethylene glycol dimethacrylate

TTEGDMA = tetraethylene glycol dimethacrylates

UDA = 7,7,9-trimethyl-4,13-dioxo-3,14-dioxa-5,12diazahexadecane-1,16-dioxy-diacrylate

UDMA = 7,7,9-trimethyl-4,13-dioxo-3,14-dioxa-5,12-diazahexadecane-1,16-dioxy-dimethacrylate

Thermoplastics/Duromers

ABS = acrylonitrile butadiene styrene copolymer

APE = aromatic polyester

CA = cellulose acetate

E/P = ethylene propylene copolymer

EP = epoxy polymer

EVA = ethylene vinyl acetate copolymer

HDPE = high density polyethylene

HMWPE = high molecular weight polyethylene

LDPE = low density polyethylene

LLDPE = linear low density polyethylene

PA = polyamide

PAA = polyacrylic acid

PAN = polyacrylonitrile

PBTP = polybutylene terephthalate

PC = polycarbonate

PDMS = polydimethylsiloxane

PE = polyethylene

PEEK = polyaryletheretherketone

PEMA = polyethyl methacrylate

PEO = polyethylene oxide

PES = polyethersulfone

PETP = polyethylene terephthalate

PF = phenol formaldehyde resin

PI = polyimide

PMMA = polymethyl methacrylate

POM = polyoxymethylene

PP = polypropylene

PS = polystyrene

PSU = polysulfone

PTFE = polytetrafluoroethylene

PU = polyurethane

PVAC = polyvinyl acetate

PVAL = polyvinyl alcohol

PVC = polyvinyl chloride

PVC-P = soft PVC - plasticized

PVC-U = hard PVC - unplasticized

SAN = styrene acrylonitrile copolymer

SB = styrene butadiene copolymer, high impact PS = HIPS

TPU = thermoplastic polyurethane

UF = urea-formaldehyde resin

UHMWPE = ultra high molecular weight polyethylene

UP = unsaturated polyester

VPE or XLPE = cross-linked polyethylene

Elastomers/Rubbers

ABR = acrylate butadiene rubber

AU = polyester urethane rubber

BR = butadiene rubber

EPR = ethylene propylene rubber

E-SBR = styrene-butadiene rubber

EU = polyether urethane rubber

FKM = fluoro rubber

IIR = isoprene isobutene rubber = butyl rubber

IR = cis-1,4-polyisoprene = synthetic rubber

NBR = acrylonitrile butadiene rubber = nitrile rubber

NCR = acrylonitrile chloroprene rubber

NIR = acrylonitrile isoprene rubber

NR = natural rubber

PBR = vinylpyridine butadiene

PDMS = polydimethylsiloxane

Composite Resins/Composite Plastics

AFP = asbestos fiber-reinforced plastic

BFK = boric fiber-reinforced plastic

CFK = carbon fiber-reinforced plastic

FK = fiber-reinforced plastic

GFK = glass fiber-reinforced plastic

MFK = metal fiber-reinforced plastic

MWK = metal whiskers fiber-reinforced plastic

SFK = synthetic fiber-reinforced plastic

UD = unidirectional fiber-reinforced plastic

Other

BPO = DBPO = dibenzoyl peroxide

CQ = camphorquinone

HQ = hydroquinone

HQME = hydroquinone monomethyl ether

M = molecular mass [g mol-1]

mass% = percent by mass, often also called wt% = percent by weight

mol = molar mass [mol] is the mass of 1 mole of a given substance divided by the amount of the substance and is expressed in g mol-1. Example: 100 g of water is about (100 g)/(18.015 g mol-1) = 5.551 mol of water

mol% = percent of mole

SEM = scanning electron microscopy

TEM = transmission electron microscopy

tert. arom. amine = tertiary aromatic amine

TPO = (2, 4, 6,-trimethylbenzoyl)diphenylphosphine oxide

vol% = percent by volume