Polymeric surface coatings
AssigneeBiocompatibles Limited
InventorsRoderick W. J. Bowers, Stephen A. Jones, Peter W. Stratford, Stephen A. Charles
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Abstract
Polymers of one or more radical polymerisable monomers which polymer has pendant groups bearing a center of permanent positive charge and other pendant groups capable of stably binding the polymer to a surface are useful in the treatment of surfaces to render them biocompatible. The polymers may contain pendant groups which bind the polymer to a surface by physisorption, covalent bonding or ionic interactions. Additionally reactive groups in the polymer may serve as points for attachment of ligands to the polymer when coated on a surface.
Claims15
A process in which a substrate having a surface is coated with a coating composition containing a polymer formed from radical polymerisable monomers including a radical polymerisable zwitterionic monomer containing a zwitterionic group and a radical polymerisable monomer containing reactive groups to form a polymer having zwitterionic groups and pendant reactive groups and the pendant reactive groups are reacted to form a stable coating of polymer on the surface by reaction of the pendant reactive groups with one another to crosslink the polymer, and wherein the zwitterionic monomer has the formula:
- Y--B--X (I)
- wherein B is a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene chain optionally containing one or more fluorine atoms up to and including perfluorinated chains, or if X contains a carbon-carbon chain between B and the centre of permanent position charge or if Y contains a terminal carbon atom bonded to B, a valence bond;
- X is a zwitterionic group selected from group IVB, IVC, IVD and IVF in which group IVB has the formula ##STR21## wherein the groups R.sup.6 are the same or different and each is hydrogen or C.sub.1-4 alkyl and d is from 2 to 4;
- group IVC has the formula ##STR22## where the groups R.sup.7 are the same or different and each is hydrogen or C.sub.1-4 alkyl, and e is from 1 to 4;
- group IVD has the formula ##STR23## wherein the groups R.sup.8 are the same or different and each is hydrogen or C.sub.1-4 alkyl, R.sup.8a is hydrogen or a group --C(O)B.sup.1 R.sup.8b wherein R.sup.8b is hydrogen or methyl, B.sup.l is a valence bond or straight or branched alkylene, oxaalkylene or oligo-oxaalkyene group, and f is from 1 to 4;
- and if B is other than a valence bond z is 1 and if B is a valence bond z is 0, if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- group IVE has the formula ##STR24## wherein the groups R.sup.9 are the same or different and each is hydrogen or C.sub.1 -C.sub.4 alkyl, R.sup.9a is hydrogen or a group --C(O)B.sup.2 R.sup.9b, wherein R.sup.9b is hydrogen or methyl, B.sup.2 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, and g is from 1 to 4;
- and
- if B is other than a valence bond z is 1 and if B is a valence bond z is 0 if X is directly bonded to an oxygen or nitrogen atom and otherwise z is 1;
- and
- group IVF has the formula ##STR25## wherein the groups R.sup.10 are the same or different and each is hydrogen or C.sub.1-4 alkyl, R.sup.10a is hydrogen or a group --C(O)B.sup.3 R.sup.10b wherein R.sup.10b is hydrogen or methyl, B.sup.3 is a valence bond or a straight or branched alkylene, oxaalkylene or oligo-oxaalkylene group, and h is from 1 to 4;
- and
- if B is other than a valence bond z is 1 and if B is a valence bond z is 0 if X is directly bonded to the oxygen or nitrogen and otherwise z is 1;
- and
- Y is an ethylenically unsaturated polymerisable group selected from ##STR26## wherein:
- R is hydrogen or a C.sub.1 -C.sub.4 alkyl group;
- A is --O-- or --NR.sup.1 -- where R.sup.1 is hydrogen or a C.sub.1 -C.sub.4 alkyl group or R.sup.1 is --B--X where B and X are as defined above;
- and
- K is a group --(CH.sub.2).sub.p OC(O)--, --(CH.sub.2).sub.p C(O)O--, --(CH.sub.2).sub.p OC(O)O--, --(CH.sub.2).sub.p NR.sup.2 --, --(CH.sub.2).sub.p NR.sup.2 C(O)--, --CH.sub.2).sub.p C(O)NR.sup.2 --, --(CH.sub.2).sub.p NR.sup.2 C(O)O--, --(CH.sub.2).sub.p OC(O)NR.sup.2 --, --(CH.sub.2).sub.p NR.sup.2 CO)NR.sup.2 --, (in which the groups R.sup.2 are the same or different --(CH.sub.2).sub.p O--, --(CH.sub.2).sub.p SO.sub.3 --, or, optionally in combination with B, a valence bond and p is from 1 to 12 and R.sup.2 is hydrogen or a C.sub.1 -C.sub.4 alkyl group
- and wherein the radical polymerisable monomer containing reactive groups has the general formula (XII)
- Y.sup.2' --B.sup.9' --O.sup.5' (XII)
- where Y.sup.2' is an ethylenically unsaturated polymerisable group selected from ##STR27## where R.sup.26' is hydrogen or C.sub.1 -C.sub.4 alkyl;
- A"' is --O-- or NR.sup.27' --, wherein R.sup.27' is hydrogen or a C.sub.1 -C.sub.4 alkyl group or R.sub.27' is a group --B.sup.9' Q.sup.5' ;
- B.sup.9' is a valence bond, a straight or branched alkylene oxaalkylene or oligo-oxaalkylene group;
- K.sup.3' is a group --(CH.sub.2).sub.x OC(O)--, --(CH).sub.x C(O))--, --(CH.sub.2).sub.x OC(O)O--, --(CH.sub.2).sub.x NR.sup.28' --, --(CH.sub.2).sub.x NR.sup.28' C(O)--, --(CH.sub.2).sub.x C(O)NR.sup.28' --, --(CH.sub.2).sub.x NR.sup.28' C(O)O--, --(CH.sub.2).sub.x OC(O)NR.sup.28' --, --(CH.sub.2).sub.x NR.sup.28' C(O)NR.sup.28' --(in which the groups R.sup.28' are the same or different), --CH.sub.2).sub.x O--, --(CH.sub.2).sub.x SO.sub.3 --, a valence bond, x' is from 1 to 12 and R.sup.28' is hydrogen or a C.sub.1 -C.sub.4 alkyl group;
- and
- O.sup.5' is a reactive group selected from the group consisting of cinnamyl, epoxy, --CHOHCH.sub.2 Hal (in which Hal is selected from chlorine, bromine, and iodine atoms), methylol, silyl, ethylenically and acetylenically unsaturated groups, acetoacetoxy and chloroalkylsulphone groups.
Dependencies are inferred from the claim text.