Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – Processes of preparing a desired or intentional composition...
Patent
1983-11-07
1986-03-04
Ivy, C. Warren
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
Processes of preparing a desired or intentional composition...
524831, 524833, 526240, 5263075, 526318, 526311, C08F22220
Patent
active
045741301
DESCRIPTION:
BRIEF SUMMARY
The present invention relates to polymerisable compounds which are also surfactants, adhesive copolymers thereof for surgical and medical use, and methods of manufacturing the same.
It is well known in the art to form polymers by emulsion polymerisation. Such processes are convenient because they avoid the use of solvents. The emulsion polymerisation process requires the use of a surfactant to form stable emulsion of monomers and other ingredients and to prevent coagulation of the polymer emulsion thus formed; usually a non-polymerisable surfactant is used. However, the residual surfactant in the polymer can be extracted by water and therefore renders the polymer sensitive to water. To minimise this problem the use of polymerisable surfactants has been proposed in the patent literature. For example, British Patent No. 1,430,136 discloses emulsion polymerised polymers as adhesives and lists copolymerisable surfactants suitable for this purpose.
Specific anionic copolymerisable surfactants which can also be used to form stable emulsions in emulsion polymerisation have now been discovered; these are readily copolymerisable, as is desirable in such surfactants.
However, although the art teaches the use of copolymerisable surfactants, the need for external non-copolymerisable surfactants has not hitherto been successfully avoided, although this would clearly be desirable.
All the examples given in the aforementioned patent show the use of copolymerisable surfactants in combination with an external non-copolymerisable surfactant.
The present surfactants can be used to form stable emulsions in emulsion polymerisation without the need for external non-copolymerisable surfactants additional thereto.
The present invention thus provides a compound having the formula (I): --CH.sub.2 --O).sub.y --OC--A--COOH (I) 20, y is an integer from 0 to 5, A is an alkylene, alkenylene, or phenylene radical such that A (COOH).sub.2 is a dibasic acid capable of forming an anhydride A (CO).sub.2 O.
Apt salts of compounds of formula (I) are water soluble and include the ammonium, water soluble alkyl substituted ammonium and akali metal salts thereof. Favoured salts of the compound of the formula (I) are the ammonium, trimethyl-ammonium, triethyl-ammonium, sodium and potassium salts. A preferred salt of the compounds of the formula (I) is the ammonium salt. Another preferred salt is the sodium salt.
The water insoluble compounds of the invention can be used as intermediates to form the water soluble compounds of the invention by ion exchange. Tne compound of formula (I) itself is water insoluble.
Preferably R is CH.sub.3.
Favoured residues A are alkylene or akenylene groups of 2 to 6 carbon atoms or pheneylene. Preferred residues A are CH.sub.2 CH.sub.2, CH.dbd.CH or ortho-C.sub.6 H.sub.4. The most preferred residue A is CH.sub.2 CH.sub.2.
A favoured value for y is 0.
Favoured values for x are 3 to 10 and more favourably 5 to 9. A preferred value for x is 7.
All values such as x and y in oligomers and polymers herein are number average values.
A highly favoured compound of this invention is the ammonium or sodium salt of compounds of formula (I) in which x is an integer from 3 to 10, y is 0, A is --CH.sub.2 --CH.sub.2 --, --CH.dbd.CH-- or --C.sub.6 H.sub.4 --. Preferred compounds of the invention are the ammonium salts of methacryloyl poly (oxypropylene) hemi succinate esters. Such compounds are favourably provided as a mixture of esters of different chain lengths containing a number average of 3 to 10 oxypropylene units per molecule. A preferred compound of this type contains a number average of 7 oxypropylene units per molecule.
Water soluble compounds of the invention are surfactants. The ammonium and alkali metal, especially the sodium salt compounds in particular have good surfactant properties. Tne ammonium salt and tne sodium salt are especially favoured for this purpose.
The surfactant compounds of the present invention can be used in emulsion polymerisation, when they will become part of the resulting polymer molecule.
Therefo
REFERENCES:
patent: 2524921 (1950-10-01), Minter
patent: 3150118 (1964-09-01), Clemens
patent: 3790533 (1974-02-01), Samour
patent: 4292419 (1981-09-01), Kamada
patent: 4384096 (1983-05-01), Sonnabend
patent: 4463150 (1984-07-01), Kelly
Derwent Abstract AN 31388v/17.
Kiamil Sinan B.
Potter William D.
Ivy C. Warren
Smith & Nephew Associated Companies p.l.c.
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