- J. Haveren van (15)
- C. Kekem van (1)
- C.E. Koning (1)
- J. Laven (1)
- M.B. Leeuwen van (1)
- R. Linde van der (6)
- M.J.J. Litjens (1)
- F. Micciche (10)
- W. Ming (4)
- B.A.J. Noordover (1)
- E.A. Oostveen (15)
- E. Oostveen (1)
- Z.O. Oyman (2)
- J. Reedijk (1)
- M. Straten van (1)
- G.A.M. Walle van der (1)
- J.G.J. Weijnen (4)
- J. Weijnen (3)
Resins and additives for powder coatings and alkyd paints, based on renewable resources
Haveren, J. van; Oostveen, E.A. ; Micciche, F. ; Noordover, B.A.J. ; Koning, C.E. ; Benthem, R.A.T.M. van; Frissen, A.E. ; Weijnen, J.G.J. - \ 2007
Journal of Coatings Technology and Research 4 (2007)2. - ISSN 1547-0091 - p. 177 - 186.
combination - acid - linoleate - oxidation
Due to limited fossil resources and an increased need for environmentally friendly, sustainable technologies, the importance of using renewable feedstocks in the paint and coatings area will increase in the decades to come. This paper highlights some of the perspectives in this area. Alkyd resins for high-solid paints and reactive diluents, completely based on commercially available renewable resources, were prepared and characterized. Alkyd resins based on sucrose and unsaturated fatty acids or oils showed a low intrinsic viscosity, making them suitable to be used in high-solid alkyd paints. Reactive diluents based on similar starting materials showed excellent properties with regard to thinning behavior and effect on drying characteristics. Powder coating polyester resins were synthesized, starting from isosorbide and diacids. Polyester resins with glass transition temperatures up to 70°C were obtained. Incorporation of small amounts of other diols and trifunctional components was found to improve color and coating properties. In order to create completely renewable resin systems, the development of renewable drying agents for alkyds and crosslinkers for powder coatings is in progress.
Novel carbohydrate based alkyd resins as binders for coatings
Oostveen, E.A. ; Haveren, J. van - \ 2006
|How biobased products contribute to the establishment of sustainable, phthalate free, plasticizers and coatings
Haveren, J. van; Oostveen, E.A. ; Micciche, F. ; Weijnen, J.G.J. - \ 2006
In: Feedstocks for the future : renewables for the production of chemicals and materials / Bozell, J.J., Patel, M.K., Washington : American Chemical Society (ACS Symposium series 921) - ISBN 0841239347 - p. 99 - 115.
Biobased components for the development of environmentally friendly, durable products are being described. The potential and versatility of isosorbide diesters as subsitutes for the currently phthalate based plasticisers for PVC and other resins, is shown. Also high solid alkyd resins for decorative paints, completely based on commercially available renewable resources are being described. Paints comprising alkyd resins based on inulin or sucrose and unsaturated fatty acids or oils, showed very good gloss, excellent levelling and a low intrinsic viscosity making them suitable to be used in high solid alkyd paints. A new concept was used to prepare effective, cobalt free, drying catalysts for alkyd paint systems. Iron in combination with ascrobic acid (vitamin C), and optionally other ligands, was found to be a very effective drying catalyst.
Oxidation and oligomerization of ethyl linoleate under the influence of the combination of ascorbic acid 6-palmitate/iron-2-ethylhexanoate
Micciche, F. ; Haveren, J. van; Oostveen, E.A. ; Ming, W. ; Linde, R. van der - \ 2006
Applied Catalysis A-General 297 (2006)2. - ISSN 0926-860X - p. 174 - 181.
unsaturated fatty-acids - metal-catalyzed autoxidation - lipid-peroxidation - mass-spectrometry - alkyd resins - linseed oil - cross-linking - paints - drier - iron(iii)
In this paper we report the oxidation and oligomerization of ethyl linoleate (EL), a model compound for alkyd resins, under the influence of iron-2-ethylhexanoate (Fe-eh) in combination with ascorbic acid 6-palmitate (AsA6p) at different AsA6p/Fe-eh molar ratios (0/1¿4/1). Reactions were studied in time by FT-IR, NMR, size exclusion chromatography (SEC) and peroxide amount determination. The oxidation and oligomerization of EL were accelerated by the combination of AsA6p and Fe-eh, and the catalytic properties of the catalysts were strongly dependent on the molar ratio AsA6p/Fe-eh. The molar ratio of 2/1 appeared to be optimal, at which both the oxidation and oligomerization of EL were the fastest. At molar ratio smaller than 2/1, or only in the presence of Fe-eh, the EL oxidation showed a time lag of up to 100 h; above the ratio 2/1 the rates of both EL oxidation and oligomerization decreased. Results are explained in terms of the multi-facet role played by AsA6p: its pro-oxidant or anti-oxidant properties, depending on the ratio of AsA6p/Fe-eh, and its effect on the Fe-eh complex.
Oxidation of methyl linoleate in micellar solutions induced by the combination of iron(II)/ascorbic acid and iron(II)/H2O2
Micciche, F. ; Haveren, J. van; Oostveen, E.A. ; Laven, J. ; Ming, W. ; Oyman, Z.O. ; Linde, R. van der - \ 2005
Archives of Biochemistry and Biophysics 443 (2005)1-2. - ISSN 0003-9861 - p. 45 - 52.
lipid-peroxidation - ascorbic-acid - hydroxyl radicals - hydrogen-peroxide - alpha-tocopherol - alkyd paints - iron - initiation - autoxidation - superoxide
The oxidation of methyl linoleate (ML) was studied in the presence of Fe(II) alone and its combination with either ascorbic acid (AsAH2) or hydrogen peroxide (H2O2) at different molar ratios. Reactions were carried out in micellar solutions of TTAB (tetradecyltrimethylammonium bromide) and SDS (sodium dodecyl sulfate), respectively, and were monitored by UV spectroscopy and electrospray ionization mass spectrometry (ESI-MS). Fe(II) alone was able to catalyze the oxidation of ML in micellar solutions of TTAB, but not in those of SDS. The combination of H2O2 with Fe(II) showed catalytic effect only in the TTAB medium, leading to different ML and Fe(II) oxidation kinetics compared to the Fe(II)-only catalyzed reactions. The AsAH2/Fe(II) combination demonstrated to be a good catalyst for the oxidation of ML in SDS micellar solutions, but not in TTAB micellar solutions; the activity of the catalyst was dependent on the AsAH2/Fe(II) molar ratio. The obtained results confirm that, for the ML oxidation to be initiated, the presence of a Fe(II)/Fe(III) couple is essential, which is related to the pH of micellar solutions. The catalytic properties of the AsAH2/Fe(II) combination were explained by taking into account the anti-oxidant and pro-oxidant properties of AsAH2, as well as the possible formation of an iron/ascorbate complex as the initiator of the ML oxidation.
Identification of mixed-valence metal clusters in drier solutions for alkyd-based paints by electrospray ionization mass spectrometry (ESI-MS)
Micciche, F. ; Straten, M. van; Ming, W. ; Oostveen, E.A. ; Haveren, J. van; Linde, R. van der; Reedijk, J. - \ 2005
International Journal of Mass Spectrometry 246 (2005)1-3. - ISSN 1387-3806 - p. 80 - 83.
cobalt(ii)-catalyzed decomposition - complexes - model
The oxidative drying of alkyd paints has many similarities with the way lipids are oxidized in biological systems. Metal salts based on Co, Fe and Mn are added to accelerate the oxidative drying of conventional alkyd paints. Although the mechanism by which alkyd paints dry has been the subject of numerous investigations, little information is available on the structure and the actual mechanism by which driers catalyze the oxidation process. In this communication we describe the identification of metal clusters in drier solutions by electrospray ionization mass spectrometry (ESI-MS). Evidence is provided for the presence of several metal clusters ranging from M3 up to M6 as well as the coexistence of mixtures of (mixed-valence) clusters in the same solution
Towards sustainability. Alkyd resins and alkyd drying agents based on renewable resources
Haveren, J. van; Oostveen, E.A. ; Micciche, F. ; Weijnen, J.G.J. - \ 2005
European Coatings Journal 2005 (2005)1-2. - ISSN 0930-3847 - p. 16 - 19.
The combination of reducing agents/iron as environmentally friendlier alternatives for Co-based driers in the drying of alkyd paints
Micciche, F. ; Oostveen, E.A. ; Haveren, J. van; Linde, R. van der - \ 2005
Progress in Organic Coatings 53 (2005)2. - ISSN 0300-9440 - p. 99 - 105.
In answer to the increased demand for Co-free driers for alkyd based paints, a biomimetic approach has been used to find suitable and environmentally friendly alternatives for Co-based driers for alkyd paints. This approach was chosen due to the resemblance between the mechanisms by which alkyd paints dry and lipids are oxidized in biological systems. As a consequence, the combination of iron with reducing agents was tested as drier for alkyd paints. Ascorbic acid and several ascorbic acid derivatives, in combination with iron salts, have been tested in alkyd emulsions, alkyd resins (or varnishes), and in a high gloss white paint formulation. We have found that the combination of iron salts with reducing agents forms an excellent drier, in terms of film hardness and particularly total drying time, compared to a commercial Co drier and a new Mn-based alternative. The effect of two nitrogen donor ligands, N,N-bis(2-ethyl-5-methyl-imidazol-4-ylmethyl)aminopropane (BIAP) and 2-ethyl-4-methylimidazole (Im), to the mixture reducing agent/iron was also studied in a high gloss white paint formulation. Outstanding total drying time of just 2.2 h was observed for the combination of ascorbic acid 6-palmitate, iron and imidazole
|Enzymatic modification of sucrose in supercritical CO2
Litjens, M.J.J. ; Leeuwen, M.B. van; Kekem, C. van; Oostveen, E.A. ; Boeriu, C.G. - \ 2004
In: 2nd International Congress on Catalysis, Hamburg, Germany, 29 August - 2 September 2004. - Hamburg : - p. 162 - 162.
|How biobased products can contribute to the establishment of sustainable coatings
Haveren, J. van; Oostveen, E.A. ; Walle, G.A.M. van der; Micciche, F. ; Weijnen, J.G.J. - \ 2004
In: 27th Fatipec congress, 19-21 April 2004, Aix-en-Provence, France. - Paris : AFTPVA - p. 907 - 920.
|Phthalate free alkyd resins, reactive solvents and plasticisers based on carbohydrates and fatty acids
Haveren, J. van; Oostveen, E.A. ; Es, D.S. van - \ 2004
In: Abstract papers of the 227th ACS national meeting, Anaheim, CA, March 28-April 1, 2004. - Washington : American Chemical Society - ISBN 9780841239241 - p. CELL - 017.
A promising environmentally-friendly manganese-based catalyst for alkyd emulsion coatings
Oyman, Z.O. ; Ming, W. ; Micciche, F. ; Oostveen, E. ; Haveren, J. van; Linde, R. van der - \ 2004
Polymer 45 (2004)22.. - ISSN 0032-3861 - p. 7431 - 7436.
resins - model - carcinogenicity - autoxidation - mechanisms - oxidation - complex - paints - drier
A manganese(IV) complex (MnMeTACN) containing 1,4,7-trimethyl-1,4,7-triazacyclononane (MeTACN), in the presence of polyamines, significantly accelerated the oxidation of ethyl linoleate (EL) emulsions, and appeared to be a potential environmentally-friendly alternative for Co-based driers that are currently widely used for alkyd emulsion coatings. The polyamines greatly enhanced the catalytic activity of MnMeTACN in decomposing the formed hydroperoxides during the oxidation of EL. (C) 2004 Elsevier Ltd. All rights reserved.
Air-drying paint compositions comprising carbohydrate-based polyesters and polyester preparation
Oostveen, E.A. ; Weijnen, J. ; Haveren, J. van; Gillard, M. - \ 2003
Octrooinummer: WO03064498, verleend: 2003-08-07.
The invention relates to a polyester obtainable by transesterification or interesterification of:(i) a carbohydrate or an acyl ester thereof, (ii) an alkyl ester of a drying fatty acid, semi-drying fatty acid or mixture thereof; and (iii) an alkyl ester of a non aromatic polycarboxylic acid. The invention further relates to a method for the preparation of a polyester comprising the step of transesterification or interesterification.
Reactive diluents and air-drying coatings comprising them
Oostveen, E.A. ; Weijnen, J. ; Haveren, J. van; Gillard, M. - \ 2003
Octrooinummer: WO03064548, verleend: 2003-08-07.
The invention relates to the use of a fatty acid modified carbohydrate obtainable by reaction of: (i) at least one carbohydrate or an acyl ester thereof; and (ii) a fatty acid, an alkyl ester thereof or a derivative thereof as reactive diluent in a coating. The invention further relates to a coating comprising at least one binder and as a reactive diluent a fatty acid modified carbohydrate obtainable by reaction of:(i) at least one carbohydrate or an acyl ester thereof; and (ii) a fatty acid, an alkyl ester thereof or a derivative thereof.
Polysaccharide esters and their use as binders in coatings
Oostveen, E.A. ; Weijnen, J. ; Haveren, J. van; Gillard, M. - \ 2003
Octrooinummer: WO03064477, verleend: 2003-08-07.
The invention relates to a polyester obtainable by transesterification or interesterification of: (i) inulin of general formula G(F)n or an acyl ester thereof, wherein G represents a glucose moiety, F represents a fructose moiety, and n is at least 2, and(ii) a drying oil, a semi-drying oil or derived alkyl esters thereof.The invention further relates to a method for the preparation of a polyester comprising the step of transesterification or interesterification.
Drier for air-drying coatings
Micciche, F. ; Oostveen, E.A. ; Linde, R. van der; Haveren, J. van - \ 2003
Octrooinummer: WO03093384, verleend: 2003-11-13.
The invention pertains to a drier composition for air-drying alkyd-based coatings, inks, or floor coverings, comprising a combination of the following components: a) a transition metal salt with the formula: (Me )( X )m in which Me is the transition metal; X represents a coordinating ligand; and k- is the valence state of the transition metal and m is the number of ligands X. b) a reducing biomolecule. The reducing biomolecule is in particular ascorbic acid or a derivative thereof, including ascorbyl palmitate.