Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Patent
1996-06-12
1998-03-24
Hampton-Hightower, P.
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
528354, 528355, 528361, C08G 6310
Patent
active
057314063
DESCRIPTION:
BRIEF SUMMARY
BACKGROUND OF THE INVENTION
This invention concerns a process for the preparation of macromonomers. More specifically, this invention concerns a process for preparing macromonomers by reaction of a lactone with a hydroxyalkylacrylate.
Lactones have found wide applicability as monomers in the preparation of many different polymers, particularly polyesters and polyurethanes. In addition, lactones can be used in the preparation of monomers containing a plurality of reactive sites. Such monomers are often referred to as macromonomers, and have found particular application in the preparation of cross-linked polymers and polymers where further chemical modification is desirable. Important examples of macromonomers result from the reaction between a lactone and a hydroxyalkylacrylate.
The reaction between a lactone and a hydroxyalkylacrylate requires the presence of a catalyst in order to achieve a commercially acceptable rate of reaction at a moderate temperature. Use of a moderate temperature is important not only for economic reasons but also because use of too high a temperature can cause extreme discolourisation of the macromonomer product.
In U.S. Pat. No. 3,655,631, strong organic carboxylic or sulphonic acids are proposed as catalysts. There is some concern that when these acids remain in the subsequently-produced polymer they could result in reduced shelf life of the polymer.
In UK Patent Application 2,101,121, tin dihalides are taught for use as catalysts for the reaction between lactones and a hydroxyalkylacrylates. Recently, there has been some concern over the toxicological properties of heavy metal compounds.
EP-A-0 108 372 teaches the use of a wide range of catalysts, including protonic acids at concentrations below 200 ppm in the reaction product although only tin compounds are exemplified. A repeat of example 1 of this application produced a gelled product having a high yellow colouration. This indicates that the processes taught in this application can be difficult to control because gelling is commonly caused by cross-linking of the macromonomer during its manufacture. Gelling is also undesirable because it renders the macromonomer intractable and unusable. Additionally, many of the applications in which macromonomers are employed, for example in the paints industry, require a substantially colourless product, so that the yellow colouration present would result in this product being unacceptable.
In Japanese patent application 61043623, perchloric acid is taught as a suitable catalyst. Perchloric acid, however, is extremely reactive and can readily form explosive mixtures with organic compounds, so it would be desirable to identify a catalyst that did not have such hazardous properties.
The processes of the prior art notwithstanding, it remains desirable to identify additional and further process for the production of macromonomers by the reaction of lactones with hydroxyalkylacrylates.
It is a first object of the present invention to provide a new or modified process for the production of macromonomers by the reaction of lactones with hydroxyalkylacrylates.
It is a second object of some or further aspects of the present invention to provide a process for the production of macromonomers by the reaction of lactones with hydroxyalkylacrylates that avoids or ameliorates the problems associated with the processes of the prior art.
SUMMARY OF THE INVENTION
According to the present invention, there is provided a process for the preparation of macromonomers by the catalysed reaction between a lactone and a hydroxyalkylacrylate, characterised in that the catalyst comprises phosphoric acid at a concentration of greater than 200 mg/kg, preferably greater than 250 mg/kg, of reaction mixture, and that the process is carried out at a temperature of from 100.degree. C. to 130.degree. C.
DESCRIPTION OF PREFERRED EMBODIMENTS
Although EP-A-0 108 372 names a number of possible catalysts for the reaction between a lactone and a hydroxyalkylacrylate, it does not specify phosphoric acid.
During the course of
REFERENCES:
patent: 3655631 (1972-04-01), Fraser et al.
patent: 4683287 (1987-07-01), Koleske et al.
Hampton-Hightower P.
Solvay Interox Limited
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