Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Polymers from only ethylenic monomers or processes of...
Patent
1992-09-03
1994-11-08
Nagumo, Mark
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Polymers from only ethylenic monomers or processes of...
568616, 568618, 25218214, 25218218, C08F 3614
Patent
active
053628322
DESCRIPTION:
BRIEF SUMMARY
This invention relates to alkoxylates of unsaturated fatty alcohols and to their use in surface coating compositions.
It has been known for some time that it is possible to prepare molecules which consist of a hydrocarbon chain and an oxyalkylene chain (usually an oxyethylene chain), and such compounds have been useful, for example, as surfactants in a variety of end uses, one typical example being surface coatings. The hydrocarbon chain may be derived from a long chain fatty alcohol, a very common example being oleyl alcohol. This alcohol has a single double bond but this double bond is very unreactive under normal polymerisation conditions and oleyl ethoxylates have enjoyed wide use in many fields where the presence of this unsaturation is of no consequence.
In those cases where, in that part of the hydrocarbon alkoxylate which is lipophilic, there is desired the presence of unsaturation which is relatively reactive with respect to an addition polymerisation reaction, special compounds have been devised. Thus, while compounds such as oleyl ethoxylate will work in the multi-polymer particle dispersions disclosed in U.S. Pat. No. 4,413,073, the preferred unsaturated surfactants described in this disclosure are more reactive and the most preferred surfactants have multiple double bonds derived from such molecules as pentaerythritol triallyl ether. Similarly, in European Published Application 0 002 252, the applicants use allylic bonds for reaction with the fatty acid chains of the water-borne alkyd resin which is described in that document.
It has now been found that it is possible to provide an unsaturated fatty alcohol alkoxylate whose unsaturation is usefully reactive. There is therefore provided, according to the present invention, a compound of the formula I ##STR2## where R, which may be the same or different, is selected from at least one of hydrogen, methyl, ethyl and phenyl, at least one R on each --OCHR--CHR-- unit being hydrogen; where m is an integer selected from 1-100; where n is an integer selected from 8 and 9.
The oxyalkylene chain of the compound is of 2-101 and preferably 6-50 units in length. The nature of the individual units is very much determined by the end use to which the compound will be put. For example, if the compound is to be a reactive surfactant in an aqueous emulsion system, the oxyalkylene chain will consist mainly, and preferably solely, of oxyethylene units. Provided that the desired balance between the lipophilic and hydrophilic portions of the surfactant can be achieved, it is possible to include a proportion of oxypropylene, oxyethylethylene or oxyphenylethylene units. These are advantageously located on the chain adjacent to the lipophilic portion as they increase the overall lipophilicity of the molecule. The preferred oxyalkylene unit is the oxyethylene unit; those compounds according to the invention which comprise oxyalkylene units other than oxyethylene units are useful as intermediates for other products, but the oxyethylene unit is the most useful and preferably all of the oxyalkylene units are oxyethylene units.
It is particularly preferred that the double bonds in the compounds of the invention exhibit opposite geometrical isomerism, that is, one is trans and the other cis, not both cis or trans.
Accordingly we provide in a particularly preferred embodiment of the invention a compound of formula I as hereinbefore described in which the double bonds exhibit opposite geometrical isomerism.
The compounds of this invention may be synthesised by any convenient means. A particularly valuable method of preparing the preferred compounds forms part of this invention. There is therefore provided a method of preparing a compound according to the invention comprising the reaction of alkylene oxide with linoleyl alcohol in the presence of a base catalyst which is a Bronsted base.
It will readily be appreciated that the structure of this alcohol is different to that of the non-oxyalkylene chain part of the compounds; linoleyl alcohol is cis-9, cis-12-octadecadienol. It ha
REFERENCES:
patent: 4396779 (1983-08-01), Edwards
Jamieson, GR et al (1967) J. Chromatog. 29, 44-48.
ICI Australia Operations Proprietary Limited
Nagumo Mark
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