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The Effect of Fatty Acid Methyl Esters on the Curing Performance and Final Properties of Thermally Cured Solvent-Borne Coil Coatings
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.
KTH, School of Chemical Science and Engineering (CHE), Fibre and Polymer Technology.ORCID iD: 0000-0003-3201-5138
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.

Place, publisher, year, edition, pages
2007. Vol. 59, no 2, 146-151 p.
Keyword [en]
Fatty acids, Reactive diluents, Coatings, Thermal curing, Film properties
National Category
Polymer Chemistry
Identifiers
URN: urn:nbn:se:kth:diva-4854DOI: 10.1016/j.porgcoat.2007.02.004ISI: 000246935500008Scopus ID: 2-s2.0-34247593705OAI: oai:DiVA.org:kth-4854DiVA: diva2:89
Note
QC 20100816Available from: 2008-09-04 Created: 2008-09-04 Last updated: 2017-12-01Bibliographically approved
In thesis
1. Thermally cured coil-coatings utilizing novel resins and fatty acid methyl esters as reactive diluents
Open this publication in new window or tab >>Thermally cured coil-coatings utilizing novel resins and fatty acid methyl esters as reactive diluents
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
Coatings, Coil-coatings, Thermal cure, Reactive diluents, Fatty acids, Transesterification, Hyperbranched polyester resins, Film properties
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4857 (URN)978-91-7415-097-1 (ISBN)
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
2. Fatty acid methyl esters as reactive diluents in solvent-borne thermally cured coil-coatings
Open this publication in new window or tab >>Fatty acid methyl esters as reactive diluents in solvent-borne thermally cured coil-coatings
2006 (English)Licentiate thesis, comprehensive summary (Other scientific)
Abstract [en]

This work describes how a fatty acid methyl ester (FAME) derived from a vegetable oil can be introduced as reactive diluent in a solvent-borne thermally cured coil-coating system. The evaluated reactive diluent, rape seed methyl ester (RME), has been evaluated both in a fully formulated clear coat system and via model studies.

A reactive diluent is a compound that acts as a solvent in the liquid paint, lowering the viscosity, and chemically reacts into the final film during cure. Introduction of a reactive diluent derived from vegetable oil give a more environmental compliant coating since a renewable material is incorporated in the coating and the amount of traditional solvent can be decreased. These positive environmental factors have increased the industrial interest.

The fully formulated clear coat studies describes how addition of reactive diluent affects rheological properties of the wet paint, film formation, incorporation, and final film properties in a hydroxyl-functional polyester/melamine coil-coating system. The coating were cured under industrial coil-coating cure conditions and analyzed with Raman, carbon-14 dating, extraction, dynamic mechanical analysis, and visually observed. Viscosity measurement of the wet paint show that RME works as a diluent. RME increase the mobility in the system enhancing the film formation process and occurrence of defect-free films. The incorporation of RME could not be confirmed by Raman analysis. However, carbon-14 dating did indicate the presence of RME that could not be extracted from the films. The appearance and mechanical properties of the films were also significantly affected by addition of RME. Dynamic mechanical analysis of the free standing films showed that the final film properties were affected by oven temperature, choice of co-solvent, and flash-off period.

Model studies were performed to further clarify how RME chemically can react through transesterification with the hydroxyl-groups of the polyester. RME and its two main components methyl oleate and methyl linoleate were reacted with primary alcohols with and without tertiary hydrogen both under low temperature (110, 130, 150, 170°C) and industrial cure conditions. The transesterification reaction was monitored with 1H-NMR and real time IR. Evaporation and side reactions, e.g. oxidation, are competing factors with the transesterification reaction. The fatty acid structure affects the conversion as a higher amount of unsaturations triggers higher degree of oxidation. The study also showed that reaction time and temperature affects the transesterification conversion, degree of side reactions, and catalyst choice.

Place, publisher, year, edition, pages
Stockholm: KTH, 2006. 25 p.
Series
Trita-FPT-Report, ISSN 1652-2443 ; 2006:24
Keyword
Fatty acids, Reactive diluents, Coatings, Thermal curing, Transesterification, Film properties
National Category
Polymer Chemistry
Identifiers
urn:nbn:se:kth:diva-4094 (URN)91-7178-442-X (ISBN)
Presentation
2006-09-29, K1, Kemihuset, Teknikringen 56, Stockholm, 14:00
Opponent
Supervisors
Note
QC 20101117Available from: 2006-09-08 Created: 2006-09-08 Last updated: 2010-11-17Bibliographically approved

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