Brush polymer coating by in situ polymerization from photoreactive surface
View Patent ↗The invention provides compositions that include crosslinking agents having multiple photoactivatable groups, such as diaryl ketones, or a diaryl ketone, such as benzophenone, and at least one polymerizable monomer, such as a zwitterionic monomer. The compositions are useful as surface coating agents that provide brush type polymeric coatings. These polymeric coatings can be used on medical devices, such as artificial joints, to reduce wear and tear between the components of the joint and thus reduce or eliminate debris generated by friction between the joint components.
1. A composition comprising a photoreactive cross-linking compound having a formula:
L-(T-C(R 1 (XP)CHR 2 GR 3 C(═O)R 4 ) m
wherein L is a linking group comprising a formula according to structure (I):
A, B, and J form a ring wherein A and J are C=O;
B is NR 11 ;
R 11 is a hydrogen atom, an alkyl group, an aryl group or denotes a bond with T;
T is —(CH 2 ) x —;
R 1 is a hydrogen atom, an alkyl, alkyoxyalky, aryl, aryloxyalkyl or aryloxyaryl group;
X is O;
P is a hydrogen atom;
R 2 is a hydrogen atom, an alkyl, alkyloxyalkyl, aryl, aryloxyalkyl or aryloxyaryl group;
G is —O—;
R 3 and R 4 are each independently an aryl;
R is a hydrogen atom, an alkyl or aryl group;
m is 2 or 3;
x is an integer from 1 to about 500; and
a polymerizable monomer.
2. The composition of claim 1 , wherein the polymerizable monomer has an acrylate, allylic, methacrylate, vinyl or diarylketone containing moiety.
3. The composition of claim 2 , wherein the acrylate, allylic, methacrylate, vinyl or diarylketone polymerizable monomer further includes a zwitterionic moiety.
4. The composition of claim 3 wherein the polymerizable monomer is N,N-dimethyl-N-acryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-methacryloyloxyethyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-acrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, N,N-dimethyl-N-methacrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, N,N-dimethyl-N-acrylamidopropyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-methacrylamidopropyl-N-(3-sulfopropyl)-ammonium betaine, N,N-dimethyl-N-acrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, N,N-dimethyl-N-methacrylamidopropyl-N-(2-carboxymethyl)-ammonium betaine, 2-(methylthio)ethyl methacryloyl-S-(sulfopropyl)-sulfonium betaine, 2-[(2-acryloylethyl)dimethylammonio]ethyl 2-methyl phosphate, 2-(acryloyloxyethyl)-2′-(trimethylammonium)ethyl phosphate, [(2-acryloylethyl)dimethylammonio]methyl phosphonic acid, 2-[(3-acrylamidopropyl)dimethylammonio]ethyl 2′-isopropyl phosphate (AAPI), 1-vinyl-3-(3-sulfopropyl)imidazolium hydroxide, (2-acryloxyethyl) carboxymethyl methylsulfonium chloride, 1-(3-sulfopropyl)-2-vinylpyridinium betaine, N-(4-sulfobutyl)-N-methyl-N,N-diallylamine ammonium betaine (MDABS),2-methacryloyloxyethyl phosphorylcholine, or N,N-diallyl-N-methyl-N-(2-sulfoethyl) ammonium betaine.
5. The composition of claim 1 , further comprising a photoinitiator, wherein the initiator is benzophenone, an acetophenone derivative, a benzoin derivative, a benzilketal, a hydroxyalkylphenone, an aminoalkylphenone, an O-acyl oximoketone, an acylphosphonate, a thiobenzoic S-ester, a triazine, a 1,2 diketone, a quinone, a coumarins, a xanthone, or mixtures thereof.
6. The composition of claim 1 , wherein the photoreactive cross linking compound has a formula:
7. The composition of claim 6 , wherein the structure of the photoreactive cross linking compound has a formula:
8. A method of modifying a substrate comprising the step of applying a composition according to claim 1 to the substrate.
9. The method of claim 8 , wherein the composition is photoactivated such that at least one photoactivatable group within the composition forms a bond with the surface of the substrate.