Organic compounds -- part of the class 532-570 series – Organic compounds – Oxygen containing
Patent
1995-09-15
1998-06-09
Cintins, Marianne M.
Organic compounds -- part of the class 532-570 series
Organic compounds
Oxygen containing
568672, C07C 4100, C07C 4300
Patent
active
057636834
DESCRIPTION:
BRIEF SUMMARY
This application is a 371 of PCT/GB94/02721 filed on Dec. 13, 1994.
This invention relates to a novel ether 2-methylbutoxy ethoxy ethanol, a process for the preparation thereof and the use thereof as a cosolvent in aqueous resin formulations.
Monoethers of diethyleneglycol in general are well known in the art. However, the specific monoether of diethylene glycol of the present invention is unique especially in its properties in aqueous based resin systems.
Accordingly, the present invention is 2-methylbutoxy ethoxyethanol represented by the formula: .multidot.O.multidot.CH.sub.2 .multidot.CH.sub.2 .multidot.O.multidot.CH.sub.2 .multidot.CH.sub.2 .multidot.OH
2-Methylbutoxy ethoxy ethanol (hereafter "2-MBDGE") is an ether which can be synthesised by the dropwise addition of 1-chloro-2-methylbutane to a stirred mixture of a molar excess of diethylene glycol and an equimolar amount of an aqueous alkali, eg sodium hydroxide, at elevated temperature under cover of a gas inert under the reaction conditions eg nitrogen. The reaction mixture is maintained at this elevated temperature over a period and then cooled. The cold reaction mixture is then extracted with a suitable solvent such as eg dichloromethane. The resultant extract in the solvent is washed repeatedly with eg water, dried and subjected to fractional distillation, suitably under a high vacuum when 2-MBDGE is collected as a colourless mobile liquid emerging at eg 82.degree. C./1 mm Hg. 2-MBDGE has a boiling point of about 240.degree. C. and was characterised by .sup.13 C NMR spectroscopy.
2-MBDGE may also be prepared by the reaction of 2-methyl butanol with ethylene oxide at elevated temperature and pressure and in the presence of a catalyst, preferably a base catalyst such as potassium acetate.
2-MBDGE, which is also called 2-methyl butyldiglycol ether, is unique in that it is capable of exhibiting unexpected behaviour as a cosolvent in aqueous resin formulations used eg in coatings and in paints. It is well known that some resins used for water-based coatings are largely incompatible with water, and that the compatibility with water can be improved by the addition of an organic solvent known as a "coupling solvent". The nature of the coupling solvent used can affect the performance of the formulated coating in several ways.
The "coupling power" of the solvent relates to how good the solvent is at increasing the solubility of the resin in water. A solvent good in this respect can, among other benefits, increase the range of humidity and/or temperature at which the coating may be successfully applied. A simple measure of the "coupling power" of the solvent may be obtained by adding water to a 30:70 by weight mixture of coupling solvent and n-heptane at room temperature, where the n-heptane acts as a model for an oleophilic resin. At some point as water addition is increased, the mixture moves from a single, homogeneous phase to a mixture of two phases. The amount of water added before the appearance of the second phase is an indication of the coupling power of the solvent. The objective is to maximise the amount of water that can be added to the coupling solvent before the second phase appears.
The rheology of a coating formulation is partly determined by the composition and phase behaviour of the water/resin/coupling solvent ternary mixture. A good coupling solvent can influence the rheology such that, eg, the process of formulating the coating is simplified by minimising viscosity variations when a solution of the resin in the coupling solvent is diluted with water. Effectively, it is believed that the coupling solvent associates preferentially with the organic phase rather than the aqueous phase. A good solvent can also improve the performance of the coating when applied to a substrate by, eg, reducing sagging and curtaining effects. Desirable rheological behaviour is related to the composition of the ternary mixture such that, when two liquid phases coexist, one of the phases should be very largely comprised of water. This behaviour is easily deter
REFERENCES:
patent: 3656881 (1972-04-01), Hemwall
patent: 4187384 (1980-02-01), Platz et al.
patent: 4898992 (1990-02-01), Stankowiak et al.
Chapman Richard George
Goodwin Stephen Paul
Hazel Nicholas John
Lucy Andrew Richard
Stewart Nevin John
BP Chemicals Limited
Cintins Marianne M.
Jones Dwayne C.
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