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Thermally cured coil-coatings utilizing novel resins and fatty acid methyl esters as reactive diluents
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
2008 (English)Doctoral thesis, comprehensive summary (Other scientific)
Abstract [en]

Solvent-borne thermally cured coil-coating resins contain large amounts of volatile organic solvents in order to obtain suitable flow for film application. This work describes how the expensive and environmental hazardous volatile organic solvent content of a solvent-borne thermally cured polyester/melamine coil-coating system can be reduced by introduction of fatty acid methyl esters (FAMEs) as reactive diluents and modification of the polyester binder resin. The evaluated reactive diluents, two rape seed methyl esters (RMEs), two linseed oil methyl esters (LMEs), and a tall oil methyl ester (TOME) have been evaluated both in a fully formulated clear-coat system and via model studies.

Viscosity measurements of wet paint mixtures showed that formulations with hyperbranched polyester binder hold lower viscosity than conventional polyester binder resins and that FAME works as a diluent. Fully formulated clear-coats were cured under simulated industrial coil-coating cure conditions and in a convection oven at lower temperatures respectively. FAME increases the mobility of the system enhancing the film formation process. Free-standing clear-coat films were analyzed with Raman, carbon-14 dating, extraction, dynamic mechanical analysis, and visual observation. Incorporation of FAME could not be confirmed by Raman analysis. However, carbon-14 dating indicated the presence of FAME that could not be extracted from the films. The mechanical properties of the films were also affected by the addition of FAMEs, oven temperature, choice of co-solvent, and flash-off period. Conventional film characterization tests on substrate supported coatings indicated that binder resin structure and cure conditions affect the final film properties.

Model studies were performed to clarify how FAME can chemically react through transesterification with the hydroxyl-groups of the polyester. The transesterification reaction between different FAMEs and primary alcohols with and without tertiary hydrogen was monitored with 1H-NMR and real time IR. Evaporation and side reactions, e.g. alkene reactions, are competing factors to the transesterification reaction. The study showed that fatty acid structure, reaction time, and temperature affect the transesterification conversion, degree of side reactions, and choice of catalyst.

A pigmented fully formulated polyester/melamine formulation with a reactive diluent was cured at full scale in an industrial coil-coating production facility. Evaluation of the final film properties showed that the coating fulfills the specification of conventional polyester/melamine coil-coating systems.

Place, publisher, year, edition, pages
Stockholm: KTH , 2008. , 59 p.
Series
Trita-CHE-Report, ISSN 1654-1081 ; 2008:56
Keyword [en]
Coatings, Coil-coatings, Thermal cure, Reactive diluents, Fatty acids, Transesterification, Hyperbranched polyester resins, Film properties
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-4857ISBN: 978-91-7415-097-1 (print)OAI: oai:DiVA.org:kth-4857DiVA: diva2:93
Public defence
2008-09-19, F3, Lindstedtsvägen 26, Stockholm, 10:00 (English)
Opponent
Supervisors
Note
QC 20100817Available from: 2008-09-05 Created: 2008-09-04 Last updated: 2010-08-17Bibliographically approved
List of papers
1. A Model Study on Fatty Acid Methyl Esters as Reactive Diluents in Thermally Cured Coil Coating Systems
Open this publication in new window or tab >>A Model Study on Fatty Acid Methyl Esters as Reactive Diluents in Thermally Cured Coil Coating Systems
2006 (English)In: Progress in organic coatings, ISSN 0300-9440, E-ISSN 1873-331X, Vol. 55, no 4, 382-387 p.Article in journal (Refereed) Published
Abstract [en]

A model study on the transesterification reaction between fatty acid methyl ester (FAME), e.g. methyl oleate, methyl linoleate, rape seed methyl ester and different alcohols in thin films have been performed. The purpose was to evaluate the possibility to use fatty acid methyl ester (FAME) as reactive diluent in thermally cured coil-coating paints. A reactive diluent must be compatible, act as a diluent, react into the film without affecting the end properties. The transesterification between the methyl ester and hydroxyl functional model compounds was monitored by 1H-NMR and real time IR. The effects addressed in the present study were compatibility, temperature, catalyst, alcohol structure, and fatty acid methyl ester (FAME) structure. Competing factors with the transesterification reaction were shown to be evaporation and side reactions i.e. oxidation. The structure of the fatty acid methyl ester (FAME) affects the conversion as a higher amount of unsaturations triggers the competing side reaction oxidation. The reaction time and temperature affects both the degree of transesterification conversion, degree of side reactions and the catalyst choice. The present study has shown that a fatty acid methyl ester (FAME) fulfils the reactivity part for a reactive diluent in a thermally cured coating system.

Keyword
Fatty acids, Reactive diluents, Coatings, Thermal curing, Transesterification
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4855 (URN)10.1016/j.porgcoat.2006.02.002 (DOI)000236698400011 ()2-s2.0-33645135234 (Scopus ID)
Note
QC 20100816Available from: 2008-09-04 Created: 2008-09-04 Last updated: 2017-11-30Bibliographically approved
2. The Effect of Fatty Acid Methyl Esters on the Curing Performance and Final Properties of Thermally Cured Solvent-Borne Coil Coatings
Open this publication in new window or tab >>The Effect of Fatty Acid Methyl Esters on the Curing Performance and Final Properties of Thermally Cured Solvent-Borne Coil Coatings
2007 (English)In: Progress in organic coatings, ISSN 0300-9440, E-ISSN 1873-331X, Vol. 59, no 2, 146-151 p.Article in journal (Refereed) Published
Abstract [en]

The solvent content of a thermally cured coil-coating paint may be reduced by introducing a reactive diluent derived from a vegetable oil and thereby producing a coating partly based on a renewable resource. A reactive diluent acts as a solvent in the liquid paint, lowering the viscosity, and is then incorporated into the film during cure. In the present study, rape seed methyl ester (RME) has been evaluated as reactive diluent in a thermally cured hydroxyl-functional polyester/melamine system. RME has suitable diluting properties and functionality to be incorporated into the dry coating. Dynamic mechanical analysis of free standing films shows that the final film properties are affected by presence of reactive diluent, oven temperature, choice of co-solvent, and flash-off period.

Keyword
Fatty acids, Reactive diluents, Coatings, Thermal curing, Film properties
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4854 (URN)10.1016/j.porgcoat.2007.02.004 (DOI)000246935500008 ()2-s2.0-34247593705 (Scopus ID)
Note
QC 20100816Available from: 2008-09-04 Created: 2008-09-04 Last updated: 2017-12-01Bibliographically approved
3. Fatty Acid Methyl Esters as Reactive Diluents in Coil-Coatings
Open this publication in new window or tab >>Fatty Acid Methyl Esters as Reactive Diluents in Coil-Coatings
2007 (English)In: Polymer preprints, ISSN 0551-4657, Vol. 48, no 2, 857-858 p.Article in journal (Refereed) Published
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-24127 (URN)
Note
QC 20100816Available from: 2010-08-16 Created: 2010-08-16 Last updated: 2010-08-16Bibliographically approved
4. Fatty Acid Methyl Ester as Reactive Diluent in Thermally Cured Solvent-Borne Coil-Coatings: The Effect of Fatty Acid Pattern on the Curing Performance and Final Properties
Open this publication in new window or tab >>Fatty Acid Methyl Ester as Reactive Diluent in Thermally Cured Solvent-Borne Coil-Coatings: The Effect of Fatty Acid Pattern on the Curing Performance and Final Properties
2008 (English)In: Progress in organic coatings, ISSN 0300-9440, E-ISSN 1873-331X, Vol. 63, no 2, 155-159 p.Article in journal (Refereed) Published
Abstract [en]

Four different fatty acid methyl esters (FAMEs): rape seedmethyl ester (RME), tall oil methyl ester (TOME), and two types of linseed oilmethyl ester (Linutin) have been studied as reactive diluents in thermally cured solvent-borne coil-coatings. The purpose was to evaluate the effect of fatty acid methyl ester structure on the curing performance and final properties of the coating. The permanent incorporation of the reactive diluent via transesterification reaction has been followed with 1H NMR analysis of model systems. Dynamic mechanical analysis (DMA) measurements, of free-standing films, showthat the glass transition temperature (Tg) decreases upon addition of the reactive diluent. Both the amount of incorporated reactive diluent and the final film properties are affected by the number and placement of alkene-bonds in the FAME.

Keyword
Fatty acids, Reactive diluents, Coatings, Thermal curing, Film properties
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4856 (URN)10.1016/j.porgcoat.2008.05.003 (DOI)000259069200002 ()2-s2.0-48549103597 (Scopus ID)
Note
QC 20100816Available from: 2008-09-04 Created: 2008-09-04 Last updated: 2017-11-30Bibliographically approved
5. Hyperbranched Aliphatic Polyesters as Thermoset Resins for Thermally Cured Coil-Coatings
Open this publication in new window or tab >>Hyperbranched Aliphatic Polyesters as Thermoset Resins for Thermally Cured Coil-Coatings
(English)Manuscript (Other academic)
Abstract [en]

Two hydroxy-functional hyperbranched aliphatic polyesters based on 2,2-dimethylol propionic acid (bis-MPA) and a partially aromatic conventional polyester have been studied as thermoset resins for solvent-borne thermally cured polyester cross-linked with melamine coatings for pre-coated sheet metal, i.e. coil-coatings. The hyperbranched polyesters differ with respect to ratio of the end-groups being either hydroxyls or alkyl esters. The rheological properties of formulations with different polyester resin composition and reactive diluent, i.e. rape seed methyl ester (RME), content have been evaluated with viscosity measurements. Films cured either under industrial cure conditions to obtain a peak metal temperature (PMT) of 232-241°C or at a lower temperature, i.e. 130°C, on untreated or organic primer coated hot dipped galvanized (HDG) steel substrates have been prepared. The film properties have been evaluated with differential scanning calorimetry (DSC), and conventional film characterization techniques i.e. adhesion, impact, Erichsen cupping, pencil hardness, micro hardness, scratch and chemical resistance tests. Formulations possessing high drying ability with maintained suitable film application viscosity were obtained using a hyperbranched polyester resin and a reactive diluent. It is proposed that a solvent-free polyester/melamine formulation with sufficient film properties to withstand the rough forming procedures associated with coil-coatings can be obtained by further modification of the resin and greater amounts of reactive diluent.

Keyword
Hyperbranched polyester resin, fatty acids, reactive diluents, coatings, thermal curing, film properties
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4853 (URN)
Note
QC 20100817Available from: 2008-09-04 Created: 2008-09-04 Last updated: 2010-08-17Bibliographically approved

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