Unsaturated Polyester Resins: Chemistry and Technology: Piotr Penczek (U) Piotr Czub Jan Pielichowski

Adv Polym Sci (2005) 184: 1–95
DOI 10.1007/b136243
© Springer-Verlag Berlin Heidelberg 2005
Published online: 26 July 2005
Unsaturated Polyester Resins: Chemistry and Technology

Piotr Penczek1 (u) · Piotr Czub2 · Jan Pielichowski2
1 Industrial Chemistry Research Institute, ul. Rydygiera 8, 01-793 Warsaw, Poland
piotr.penczek@ichp.pl
2 Cracow University of Technology, ul. Warszawska 24, 31-155 Cracow, Poland
pczub@usk.pk.edu.pl, pielich@usk.pk.edu.pl
1 Introduction . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5
2 Major Raw Materials . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5

2.1 Dicarboxylic Acids and Acid Anhydrides . . . . . . . . . . . . . . . . . . . 6
2.2 Glycols and Other Polyhydric Alcohols . . . . . . . . . . . . . . . . . . . . 14
2.3 Crosslinking Monomers . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 19
2.4 Dicyclopentadiene . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 22
2.5 Manufacture of UPRs Using PET Scrap . . . . . . . . . . . . . . . . . . . . 28
3 Vinyl Ester Resins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30
4 Flexibilization . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 35
4.1 Incorporation of Segmental Modifiers into the UP Molecules . . . . . . . . 35
4.1.1 Terminal Poly(oxyethylene) Segments in the UPs . . . . . . . . . . . . . . . 35
4.1.2 UPs with Incorporated Perfluoropolyether Segments . . . . . . . . . . . . . 35
4.1.3 Copolymerizable Rubber Flexibilizers . . . . . . . . . . . . . . . . . . . . . 36
4.2 Interpenetrating Polymer Networks . . . . . . . . . . . . . . . . . . . . . . 38
5 Decrease in Styrene Emission . . . . . . . . . . . . . . . . . . . . . . . . . 41

5.1 With Low-Volatility Monomers . . . . . . . . . . . . . . . . . . . . . . . . . 41
5.2 With Wax-Like Additives . . . . . . . . . . . . . . . . . . . . . . . . . . . . 42
6 Decrease in Flammability and Smoke Emission . . . . . . . . . . . . . . . 43
7 Chemical and Alkali Resistance . . . . . . . . . . . . . . . . . . . . . . . . 46
8 Thermal Degradation . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 49
9 Chemical Analysis and Structural Investigation of Crosslinked Polyesters 50

9.1 Spectrometry . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 51
9.2 Other Methods . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 59
10 Curing of Unsaturated Polyesters and Vinyl Ether . . . . . . . . . . . . . . 62

10.1 Initiators: Peroxides . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 62
10.2 Promoters . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 63
10.2.1 Cobalt Accelerators . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
10.2.2 Aromatic Amines . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 64
10.3 Photopolymerization: Maleimides and Vinyl Ethers . . . . . . . . . . . . . 66
10.4 Copolymerization Kinetics, Thermochemistry and Rheology . . . . . . . . 68
2 P. Penczek et al.
11 Low-Shrink and Zero-Shrink Systems . . . . . . . . . . . . . . . . . . . . . 77

11.1 Compositions with Thermoplastic Additives . . . . . . . . . . . . . . . . . 77
11.2 Mechanism of Decrease in Shrinkage . . . . . . . . . . . . . . . . . . . . . 78
12 UPR-Based Nanocomposites . . . . . . . . . . . . . . . . . . . . . . . . . . 80
13 Major Application Processes . . . . . . . . . . . . . . . . . . . . . . . . . . 84

13.1 Composites with Glass Fibers and Natural Fibers . . . . . . . . . . . . . . . 85
13.2 Composites Reinforced with Fillers . . . . . . . . . . . . . . . . . . . . . . 86
13.3 Molding Compounds . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 87
13.4 Powder Coatings from UPs . . . . . . . . . . . . . . . . . . . . . . . . . . . 89
References . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 90
Abstract Results of investigations on novel formulations, structure-property relation-

ships, curing, and compositions with fillers and reinforcing fibers (1997–2004) are re-
viewed with about 200 references to articles and several references to patents. The
following topics are considered in particular: novel dibasic acids, glycols, crosslinking
monomers, and curing systems, “vinyl ester” resins, fire retardant materials, IPNs and
other systems comprising built-in thermoplastic polymers and oligomers with terminal
functional groups. Information on unsaturated polyesters manufactured using PET scrap
is given. Analytical (mainly spectrometric) methods for studying the chemical structure
of crosslinked unsaturated polyester resins are presented. Approaches to the decrease in
styrene emission on processing of unsaturated polyester resins are also discussed.
Keywords Unsaturated polyester resins · Reinforced polyesters ·

Poly(ethylene terephthalate) · Vinyl ester resins · Curing
Abbreviations
∆Hr heat released
ρv depolarization ratio
AFM atomic force microscopy
APP ammonium polyphosphate
ATH aluminum trihydroxide Al(OH)3
BHET bis(hydroxyethyl)terephthalate
Bis-GMA 2,2-bis[4-(3-methacryloyloxy-2-hydroxypropoxy)phenyl]
BMC bulk molding compounds
BMI bismaleimide
CDRE convulsion difference resolution enhancement
CMDB composite modified double-base
CoHx cobalt hexanoate
CoNp cobalt naphthenate
CP/MAS magic angle spinning
CPD cyclopentadiene
CTBN carboxyl terminated poly(butadiene-co-acrylonitrile)
DAD diode array detection
DCPD dicyclopentadiene
DD dipolar decoupling
DEF diethyl fumarate
DEPT distortionless enhancement by polarization transfer

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Adv Polym Sci (2005) 184: 1–95

Unsaturated Polyester Resins: Chemistry and Technology

2 Major Raw Materials . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 5

3 Vinyl Ester Resins . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . . 30

5 Decrease in Styrene Emission . . . . . . . . . . . . . . . . . . . . . . . . . 41

6 Decrease in Flammability and Smoke Emission . . . . . . . . . . . . . . . 43

7 Chemical and Alkali Resistance . . . . . . . . . . . . . . . . . . . . . . . . 46

9 Chemical Analysis and Structural Investigation of Crosslinked Polyesters 50

10 Curing of Unsaturated Polyesters and Vinyl Ether . . . . . . . . . . . . . . 62

11 Low-Shrink and Zero-Shrink Systems . . . . . . . . . . . . . . . . . . . . . 77

13 Major Application Processes . . . . . . . . . . . . . . . . . . . . . . . . . . 84

Abstract Results of investigations on novel formulations, structure-property relation-

Keywords Unsaturated polyester resins · Reinforced polyesters ·

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