US20040144655A1 - Process for depositing strong adherend polymer coating onto an electrically conductive surface - Google Patents
Process for depositing strong adherend polymer coating onto an electrically conductive surface Download PDFInfo
- Publication number
- US20040144655A1 US20040144655A1 US10/727,041 US72704103A US2004144655A1 US 20040144655 A1 US20040144655 A1 US 20040144655A1 US 72704103 A US72704103 A US 72704103A US 2004144655 A1 US2004144655 A1 US 2004144655A1
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- Prior art keywords
- process according
- polymer
- coating
- monomer
- grafting
- Prior art date
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- RCINICONZNJXQF-MZXODVADSA-N taxol Chemical compound O([C@@H]1[C@@]2(C[C@@H](C(C)=C(C2(C)C)[C@H](C([C@]2(C)[C@@H](O)C[C@H]3OC[C@]3([C@H]21)OC(C)=O)=O)OC(=O)C)OC(=O)[C@H](O)[C@@H](NC(=O)C=1C=CC=CC=1)C=1C=CC=CC=1)O)C(=O)C1=CC=CC=C1 RCINICONZNJXQF-MZXODVADSA-N 0.000 description 1
- 229940124597 therapeutic agent Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- WLPUWLXVBWGYMZ-UHFFFAOYSA-N tricyclohexylphosphine Chemical compound C1CCCCC1P(C1CCCCC1)C1CCCCC1 WLPUWLXVBWGYMZ-UHFFFAOYSA-N 0.000 description 1
- YFHICDDUDORKJB-UHFFFAOYSA-N trimethylene carbonate Chemical compound O=C1OCCCO1 YFHICDDUDORKJB-UHFFFAOYSA-N 0.000 description 1
- 239000012989 trithiocarbonate Substances 0.000 description 1
- 238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000004876 x-ray fluorescence Methods 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Images
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- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/10—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to inorganic materials
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- C08F265/00—Macromolecular compounds obtained by polymerising monomers on to polymers of unsaturated monocarboxylic acids or derivatives thereof as defined in group C08F20/00
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- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
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- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
- C08F293/005—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule using free radical "living" or "controlled" polymerisation, e.g. using a complexing agent
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- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/003—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/08—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C09D151/00—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers
- C09D151/10—Coating compositions based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Coating compositions based on derivatives of such polymers grafted on to inorganic materials
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/44—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications
- C09D5/4476—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes for electrophoretic applications comprising polymerisation in situ
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- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/003—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained by reactions only involving unsaturated carbon-to-carbon bonds
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- C09J151/00—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J151/08—Adhesives based on graft polymers in which the grafted component is obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers grafted on to macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
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- C08F2438/00—Living radical polymerisation
- C08F2438/01—Atom Transfer Radical Polymerization [ATRP] or reverse ATRP
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- C08F2438/00—Living radical polymerisation
- C08F2438/02—Stable Free Radical Polymerisation [SFRP]; Nitroxide Mediated Polymerisation [NMP] for, e.g. using 2,2,6,6-tetramethylpiperidine-1-oxyl [TEMPO]
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- C08F2800/00—Copolymer characterised by the proportions of the comonomers expressed
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- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Definitions
- the invention concerns a process for depositing by electro-grafting a polymer coating onto an electrically conductive surface.
- film thickness is small ( ⁇ 100 nm) due to a fast termination of grafted polymer brushes, and the monomers which can be electrografted are restricted to one (although large) family of activated vinylic monomers e.g.acrylate, cyano, cyano-acrylate, pyridine . . . compounds.
- the carbon-carbon double bond must be activated by an electron withdrawing substituent for the monomer to be reactive at the cathode and to be adsorbed on it preferably to the solvent.
- any function such as alcohol, protic amine and carboxylic acid, which are reduced at a less cathodic potential than the monomer cannot be tolerated.
- the surface of the substrate belongs to metallic prostheses such as for example structure-support implants, as for example bones plates, bone screws, femoral heads, stent, dental implants problems of biostability and biocompatibility are important.
- stent which serves as scaffolding to the vessel wall after percutaneous vessel enlargement
- a well known limitation to existing stents is their limited hemo and tissue-compatibility.
- inflammatory response does occur which in turn might promote local thrombosis activation and/or smooth muscle cells and myofibroblasts migration and proliferation.
- Stent implantation might also delay normal endothelial regeneration after vessel injury. This might ultimately results in further lumen obstruction impeding normal blood flow to the heart. This process has been called restenosis. Therefore, there is a need to develop more biocompatible stent possibly capable to release bioactive compounds to modify tissue reactions to metallic stent implantation.
- barrier coatings capable either to prevent corrosion of the underlying metal (cars, medical devices such as stems, dental implants, guidewires etc), or to disfavor adsorption of biological molecules onto the surface when put into contact with biological fluids and/or implanted.
- Such problems is encountered e.g. in biochips (non specific adsorption, which affects signal-to-noise detection ratios), and in general on the active zone of physical or chemical sensors (e.g. adsorption of proteins on pressure sensors, glucose sensors etc), as well as for packaging applications on micro-systems (should they be implanted or not).
- polymers stemming from electro-graftable monomers often fail to provide a good a durable protective coating, either because of their structure, or because of their low thickness, or both.
- very low thickness is also synonymous with a high sensitivity to scratching: the thickness of traditional electro-grafted polymers is by far lower than the rugosity of the surface of most objects, which thus pit the electro-grafted layer as soon as they are put into contact with it, ruining its tentative protective characteristics.
- Intermediate thicknesses i.e. of the order of a micron or of a few microns are also desirable to get insulating layers capable of resisting mechanical contact, insertion/desinsertion or friction cycles, such as in connectic (computers, mobile phones . . . etc), micromechanics and electrical devices in put into contact with the polymer coating.
- the rugosity of the metallic part is higher than one micrometer (since getting to lower rugosities requies specific treatments), and durable coatings must therefore be thicker than one micron.
- One definite advantage of the electro-grafting is the capability to force the formation of interface—presumably covalent—carbon/metal bonds, with high grafting ratios: parameters of the electrochemical protocol can be defined to favour the formation of grafted polymer brushes, for which controlling the thickness amounts to controlling the molecular mass of the grafted chains.
- parameters of the electrochemical protocol can be defined to favour the formation of grafted polymer brushes, for which controlling the thickness amounts to controlling the molecular mass of the grafted chains.
- the growth of polymer chains is probably hindered and stopped at an early stage, leading to pretty short chains, or in any case to chains the length of which cannot be easily controlled on the basis of traditional macromolecular strategies.
- a first direction towards obtaining thicker polymer films is thus to be able to achieve the grafting of polymer chains of high molecular mass.
- Microsystems designed for biomedical applications are packaged by biocompatible coatings of polymeric nature, such as e.g. parylene (which is deposited by Chemical Vapor Deposition, CVD) or PDMS (Poly DiMethyl Siloxane), which enable a correct biocompatibility as well as an interesting chemical resistance.
- High performance lubrication capabilities i.e. low friction coefficients—are offered by perfluoro polyether layers, e.g. on connectors or mechanical parts. None of these polymers can be obtained as the result of electro-initiated propagation reaction. Identically, one cannot straightforwardly get e.g.
- electro-grafted poly-imides poly-amides (which are good candidates in microelectronics for highly insulating polymers as they afford low k dielectric layers), and in general polymers obtained by polycondensation reactions.
- vinylic polymer may provide properties identical to these materials, the need is great to provide a process thanks to which these polymers may nevertheless be grafted onto conducting surfaces.
- electro-grafted polymers offer a restricted catalog of functionalities to fix additional layers by conventional chemical methods, such as those used e.g. in the solid support synthesis of peptides, the fixing of olinucleotides (DNA chips) or proteins (protein chips).
- DNA chips olinucleotides
- proteins protein chips
- the present invention provides a process for depositing by electro-grafting a strong adherent polymer coating on an electrically conductive surface comprising an electrochemical grafting at the surface of an active monomer for forming a primer coating P onto said surface and having as general formula:
- R represents hydrogen or methyl
- the monomer comprises an X group which is part of a preformed polymer or
- [0021] is an anchoring group for attachment of a molecule having at least one complementary reactive group.
- the monomer becomes a macromonomer bearing at least one activated vinylic pendant group, e.g. an acrylic or methacrylic function.
- activated vinylic pendant group e.g. an acrylic or methacrylic function.
- Such process also allows further modification of an initial electrografted polymer coating (called primer coating P) to increase the coating thickness by the so-called grafting-from technique i.e. polymerization of a second monomer (called M in FIG. 2, see below) or to introduce other types of polymers (also called top coating) via covalent attachment between the primer and the top coating through the X ester group by the so-called grafting-onto technique.
- primer coating P an initial electrografted polymer coating
- M second monomer
- top coating also called top coating
- Such process also allows to graft onto the primer coating compounds like functional polymer, peptide, protein, oligonucleotide, dyes, drugs, anti bacterian compounds.
- FIG. 1 schematically illustrates electrografting of a monomer on a conductive surface S with a solvent A and a conducting salt B to form a primer electrografted polymer coating P.
- FIG. 2(I) schematically illustrates formation of a top-coating (TC) by a grafting-from technique i.e. polymerization of a second monomer M from the group X of an electrografted polymer which serves as grafted macroinitiator or transfer agent.
- FIG. 2(II) schematically illustrates formation of a top-coating (TC) by a grafting-onto technique i.e. introduction of other types of preformed polymers or any reactive molecule or macromolecule (O-Y) via covalent attachment between the primer P and the top coating TC through the X ester group of an electrografted monomer.
- TC top-coating
- O-Y reactive molecule or macromolecule
- FIG. 3 schematically illustrates electrografting of macromonomers ((1)-(2) or (3)).
- FIG. 4 exhibits a voltammogram showing passivation of a cathode by polyethyl acrylate coating (PEA).
- FIG. 5 exhibits a voltammogram for electrografting of 1-acryloxy-2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane (ATEMPO) (a) first scan (b) second scan on the same cathode.
- ATEMPO 1-acryloxy-2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane
- FIG. 6 exhibits a plot of Raman signal intensity at 1000 cm ⁇ 1 versus grafted polystyrene molecular Mass Mn measured on samples prepared by initation of styrene by nitroxide mediated radical polymerization (NMP) from the poly(ATEMPO) electrografted coating for various amounts of free alkoxyamine in solution.
- NMP nitroxide mediated radical polymerization
- FIG. 7 exhibits a volammogram for electrografting of poly(2-chloropropionate ethyl acrylate.
- (b) second scan illustrates passivation of the cathode by the resulting electrografted polymer coating.
- FIG. 8 exhibits a plot of Raman signal intensity at 1000 cm ⁇ 1 versus a grafted polystyrene molecular Mass Mn measured on samples prepared by initation of styrene by atom transfer radical polymerization (ATRP) in presence of various amounts of benzyl bromide.
- FIG. 9 exhibits a voltammogram for electrografting of a macromonomer: poly(4-acryloyloxy- ⁇ -caprolactone-co- ⁇ -caprolactone) (a) first scan (b) second scan showing passivation of the cathode by the resulting electrografted polymer coating.
- FIG. 10 exhibits a cyclic voltammograms at various scanning rates for ferrocene amine grafted-onto polyacrylate succinimide (grafting-onto technique).
- FIG. 11 exhibits UV-VIS spectra recorded for biotine-cadaverine grafted onto polyacrylate succinimide (a) after formation of a complex with dimethylaminocynnamaldehyde (b) before complex formation.
- FIG. 12 illustrates release of Rhodamine-6G from apoly- ⁇ -caprolactone coating.
- Scheme 1 illustrates a three-step preparation pathway for a poly( ⁇ -caprolactone) coating by ring opening polymerization of ⁇ -caprolactone from electrografted polyethylacrylate.
- Scheme 2 illustrates electrografting of 1 -acryloxy-2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane (1) and subsequent grafting from of polystyrene by nitroxide mediated radical polymerization (2).
- Scheme 3 illustrates electrografting of poly(2-chloropropionate ethyl acrylate) and the subsequent grafting from of polystyrene by atom transfer radical polymerization.
- Scheme 4 illustrates various structures of macromonomers based on poly( ⁇ -caprolactone) backbone and suitable for direct electrografting.
- Scheme 5 illustrates structure of a macromonomer based on poly(ethylene glycol) backbone used for directelectrografting.
- Scheme 6 illustrates electrografting of N-acryloyloxysuccinimide (a) and a subsequent grafting onto of polystyrene containing primary amine groups (b).
- macromonomer By macromonomer, one means, a preformed polymer bearing at least one acrylic or methacrylic function as illustrated in FIG. 3.
- intermediate agent one means an initiator or a transfert agent for a polyaddition reaction.
- the conducting surface according to the invention is for example steel, stainless steel, Inox316L, tantalum, titanium, nitinol, carbon, ITO glass, transition metal (Fe, Ni, Cu. Au, Ag, . . . ), metal doped polymer.
- the electrochemical grafting at the surface is performed under well known conditions from a solution of the monomer in an aprotic solvent A containing a conducting salt B.
- the monomer solution is subjected to electrolysis so as to create a reaction for example a cathodic reaction wherein the conductive surface to be coated is used as cathode at a potential situated in the range of the electron transfer between the conductive surface and the monomer of a value equal or near the value corresponding to an inhibition peak of the cathodic reaction of the monomer, but less negative than the second reduction peak corresponding to the polymerization in solution and degrafting of the polymer coating.
- a first approach to solve the problems mentioned above is to combine the electro-grafting technique with a polymerization reaction.
- the present invention provides a process for depositing by electro-grafting a polymer coating on an electrically conductive surface comprising an electrochemical grafting at the surface of an active monomer for forming a primer coating P onto said surface and having as general formula:
- R represents hydrogen or a methyl
- the X group is an intermediate agent for polyaddition reaction.
- the monomer is bearing an intermediate agent of polymerization in the ester group X and is electrografted onto the solid surface.
- the intermediate agent may be an initiator for ring opening polymerization (ROP), for polymerization via nitroxyde radicals (NMP), for atom transfer polymerization (ATRP) or a transfert agent for polymerization via reversible-addition-fragmentation (RAFT).
- ROP ring opening polymerization
- NMP nitroxyde radicals
- ATRP atom transfer polymerization
- RAFT reversible-addition-fragmentation
- This type of approach is particularly interesting as it allows a global covalent grafting of a variety of polymers onto conductive surfaces which is much larger than the restricted list of polymers whose monomers is strictly eligible for electro-grafting.
- the later list is the one dictated by the aforementioned constraints of cathodic electro-grafting, namely the absence of labile protons, and the activation of the vinylic double bond by electron withdrawing groups.
- this new type of approach allows coatings of polymers other than polyacrylates or polymethacrylates.
- Such new approach allows coatings of polymers such as for example polystyrene or polyhydroxy ethylacrylate to be deposited on the conducting substrates with a strong adhesion and an increased and tunable thickness.
- the polyaddition according to the invention may be controlled or not. It may be a ring opening polymerization (ROP)[as described by P; Dubois et al. in; Makromol. Chem., Macromol. Symp. 42/43, 1991, 103], a radical polymerization such as for example atom transfer polymerization (ATRP) [as described in Matyjaszewski, Curr. Org. Chem., 2002, 6, 67], polymerization via nitroxyde radicals (NMP) [as described in Chem.
- ROP ring opening polymerization
- ARP atom transfer polymerization
- NMP nitroxyde radicals
- the Ring opening polymerization may be applied to lactones and lactides such as (E-caprolactone), and functional caprolactones such as y-bromo E-caprolactone, or lactide such as D,L-Lactide . . . or any other polymerizable cyclic monomer such as trimethylene carbonate, cyclic anhydride, glycolide . . . .
- X may be a metal carboxylate such as aluminium carboxylate or a metal alkoxide such as aluminium alkoxide, stanneous alkoxide, titanium alkoxide, magnesium alkoxide or zinc alkoxide.
- Monomers used as precursor for ROP process are for example trimethylsilylhydroxy(meth)acrylate, glycidyl (meth)acrylate, ethyl acrylate ROP experimental conditions are well known by the man skilled in the art.
- the radical polymerization may be applied for the obtention of vinyl polymer of a wide range and predetermined molecular weight.
- radical polymerization examples include ATRP, AMP, RAFT.
- an alkoxyamine is used as initiator and mediator:
- a C—O bond of the alkoxylamine is thermally homolytically cleaved into two free radicals: a carbon centered radical, to initiate the polymerization and a nitroxide radical to regulate the radical polymerization.
- the cleavage of the C—O bond occurs by heating at a temperature between 40° C. and 160° C., preferably 110° C.
- X may be a haloalkane, haloketone, haloester, halonitrile, haloalkylbenzene or sulfonyl chloride or any other function able to initiate atom transfer radical polymerization.
- an additional metallic complex has to be added with the monomer to catalyze the polymerization.
- the metal of such catalyst has to be chosen to be compatible with the surface. On easily oxidizable surfaces like iron, a commonly used cupper catalyst has to be replaced by a more stable ruthenium based catalyst.
- RAFT reversible-addition-fragmentation
- X may be for example a dithioester, a dithiocarbamate, a trithiocarbonates or any other function able to control reversible-addition-fragmentation polymerization.
- a combination of the electro-grafting technique with a polymerization reaction as mentioned in the first aspect of the present invention allows a controllable increase in the thickness of the coating at the surface and a better adherence of the polymer coating.
- a second approach to solve the above problems is to use a macromonomer instead of a monomer.
- the present invention provides a process for depositing by electro-grafting a polymer coating on an electrically conductive surface comprising an electrochemical grafting at the surface of an active monomer for forming a primer coating onto said surface and having as general formula:
- R represents hydrogen or methyl
- the monomer becomes a macromonomer bearing at least one acrylic or methacrylic function to be electrografted on the surface S as illustrated in FIG. 3.
- the preformed polymer may be obtained by any type of polymerization technique such as by a controlled/living polymerization or not.
- the preformed polymer may be obtained for example by a polyaddition process with anionic, cationic, coordinative or radical initiation or by a polycondensation process.
- the macromonomer may be an ⁇ - or an ⁇ -, ⁇ -acrylic or methacrylic substituted polymer, a randomly acrylic or methacrylic functionalized copolymer, a diblock copolymer with one block bearing the acrylic or methacrylic groups, or any kind of macromolecular architecture (like stars, graft, tapered copolymers) which comprise active acrylic or methacrylic groups.
- FIG. 3 illustrates different examples of macromonomers. Macromonomer (1) is a polymer with pendent acrylic or methacrylic groups, Macromonomer (2) is a ⁇ functionalized polymer and (3) is an ⁇ - ⁇ functionnalized polymer.
- the macromonomer has to be compatible with the electrode polarization, so that no other electroactive functions in the range of electrografting potential, except the acrylic or methacrylic groups, is present on the macromolecular architecture. For instance, no unprotected alcohol, no carboxylic acid, no amine, no bromide should be present along the polymeric chain.
- the macromonomer has also to be soluble in the electrochemical bath i.e. in polar solvents like dimethylformamide, dimethylsulfoxide, pyridine, acetonitrile, hexamethylphosphoramide, . . . .
- a third approach to solve the above problems is to combine electro-grafting with a grafting onto technique.
- the present invention provides a process for depositing by electro-grafting a polymeric coating on an electrically conductive surface comprising an electrochemical grafting at the surface of an active monomer for forming a primer coatingP onto said surface and having as general formula:
- R represents hydrogen or methyl
- X is an anchoring group for attachment of a molecule having at least one complementary reactive group.
- X may be for example a succinimidyl group particularly reactive towards amines. It may also be an epoxy, a vinyl, an allyl, an aryl, a chloride group or a combination of them.
- Electro-grafting of such monomer provides a surface modified with a thin organic primer P suitable for further “grafting onto” process of a very wide range of molecules or macromolecules forming a new top coating (TC) onto the primer coating P.as illustrated in FIG. 2(II).
- molecules or macromolecules to be used according to such aspect of the invention may be of various architecture obtained either by polycondensation or polyaddition reaction and bearing at least one complementary reactive group. They may be (for instance aminopolystyrene, aminopolyimide, aminopolydimethylsiloxane, . . . ), proteins, enzymes, oligonucleotides, drugs, dyes, or small organic molecules of particular interest like electroactive molecules (aminoferrocene), vitamine (biotine), ligands, . . . .
- the combination of the electrografting technique with a grafting onto process of a very wide range of molecules or macromolecules as mentioned in the third aspect of the present invention is also advantageous to increase the coating thickness and to obtain a strong adhesion of the top coating.
- the coated polymer may be used to entrap or immobilize a biologically active molecule (D).
- D biologically active molecule
- these coatings are designed to be biocompatible and to play a biological function either intrinsically or by serving as a reservoir for biologically active molecules, they allow said molecules to play a biological function by local release or contact with adjacent tissues.
- the polymer coating is then able to withstand mechanical stress and sterilization process. In the particular case of coronary stems, the polymer coating is able to withstand deformation such as that induced by the inflation of the balloon for optimal stent deployment.
- said biologically active molecules are chosen for their ability to improve stent biocompatibility.
- Said active molecules might prevent, limit or suppress neointima formation, thrombosis or inflammatory response after stent implantation.
- said active molecules might accelerate normal endothelial cell regeneration after stent implantation.
- Such agents must have clear antiproliferative or antithrombotic or anticoagulant or endothelial-growth promoting capabilities.
- One such agent is a beta, alpha or gamma isotope which is complexed with an chelating agent and which might be incorporated into the proposed coating.
- the chelating agent may be hydrophilic or hydrophobic.
- chelating agents are ethylene diaminetetraacetic acid (EDTA), diethylene triaminepentaacetic acid (DTPA) and its analogues N-[2 amino-3-(rho-nitrophenyl)propyl]-trans-cyclohexane-1,2-diamine-N,N′,N′′ pentaacetic acid (nitro-CHX-A-DTPA) or 2-methyl-6-(rho-nitrobenzyl)-1,4,7 triazaheptane-N,N,N′,N′′,N′′-pentaacetic acid (nitro-1B4M-DTPA or nitro-MX DTPA) or deferoxamine (DFO) and derivatives, hydroxyethyl starch-conjugated deferoxamine (HES-DFO), 4 aminobenzylderivativetriethlenetetraaminohexaacetic acid (TTHA), 1,1 bis[(11
- This type of encapsulation is also useful to design coatings capable of releasing locally proteins and oligonucleotides, and in general any molecule or macromolecule which may play a part in any biological reaction coming into play in the physiological acceptance of the object on the surface of which the polymer layer has been grafted.
- any miscible polymers may be blended with the coating polymer from a solution in a solvent for both polymers by solvent casting or spin coating. Such blending is an additional way to increase the coating thickness.
- the metallic device was immersed in a solution containing ethyl acrylate as monomer (EA, 1M, Acros), tetraethylammonium perchlorate (TEAP, 0.05 M) in dimethylformamide (DMF, Aldrich).
- EA ethyl acrylate as monomer
- TEAP tetraethylammonium perchlorate
- DMF dimethylformamide
- M273A EG&G potentiostat/galvanostat
- AE 1M in DMF+TEAP a) first scan, b) second scan). It was held at this value until the current is decreased due to passivation of the metallic device, by the poly(ethyl acrylate) coating (PEA). This passivation was confirmed by the absence of reduction during a second potential scanning.
- the PEA-coated metallic device was washed repeatedly with DMF and acetonitrile.
- the thin PEA coating having a thickness inferior to 100 nm was characterized by IR-RAS spectroscopy.
- IR-RAS spectra were recorded by a reflexion-absorption technique (Brucker spectrophotometer) directly onto the modified electrodes whose surface reflects light. IR-RAS spectra exhibit the C ⁇ O ester band at 1739 cm ⁇ 1 .
- the modified electrode with PEA (P in FIG. 1) was dried by repeated azeotropic distillation of toluene.
- DiBAlH diisobutyl aluminum hydride
- hexane 1 10 ⁇ 3 mol/l
- ethyl ester was transformed into aluminum alkoxide (Scheme 1, step 2), initiator of the ring opening polymerization at RT of E caprolactone.(Aldrich)
- the reduction of ethyl ester was confirmed by IR-RAS spectroscopy.
- IR-RAS spectra were recorded by a reflexion-absorption technique under air (Brucker spectrophotometer) directly onto the surface modified light-reflecting steel electrodes; the intensity of the transmitted signal being dependent on the film thickness). Since the aluminum alkoxide are unstable in the air, the reduced PEA is washed with non dried toluene which promoted the hydrolysis of alkoxide groups into alcohol for easy spectral characterization purpose. The large band at 3380 cm ⁇ 1 is characteristic of alcohol groups which means that the alkoxide was previously formed. The band of ester carbonyl bond at 1739 cm ⁇ 1 has decreased in intensity after a reduction time of 16 hrs, and has disappeared after 24 hrs. which underlines the bonding of the initiator.
- the metallic device was washed extensively in toluene (Soxhlet extractor 4 days to 1 week) in order to remove the unreacted monomer and non grafted polymer if any, and then dried under vacuum.
- the poly( ⁇ -caprolactone) coating (PCL) was confirmed by IR-RAS.
- the characteristic band of carbonyl groups of the PCL backbone was observed at 1728 cm ⁇ 1 .
- the intensity of the signal depends on the polymerization time meaning that the polymer thickness increases with the polymerization time.
- adhesion strength higher than 1070N/m was obtained (adhesion strength of the tape onto the top-coating) and the PCL top coating remains attached onto the metallic device after peeling.
- adhesion strength values of PCL cast films from chloroform solution was 830 N/m when PCL is solvent cast onto reduced PEA electropolymerized on steel and 70 N/m when PCL is solvent cast onto PEA electropolymerized on steel. In these both cases the PCL top coating was completely removed from the surface.
- a steel or a nickel plate was immersed in a dry DMF solution of 1-acryloxy-2 phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane (monomer hereafter called ATEMPO where X is a group bearing a nitroxyde type radical).
- ATEMPO 1-acryloxy-2 phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane
- the monomer is electrografted in the same experimental conditions as example 1, but ethylacrylate is replaced by the ATEMPO monomer.
- a decrease in the current intensity (curve b: second scan) is the signature of the electrode passivation by the formation of a polymer; coating.
- X-ray photoelectron spectroscopy was performed on such samples (XPS was performed under ultra high vacuum (UHV), with a VG-ESCALAB I 20 220iXL spectrometer and the monochromatised Al Ka radiation at 1486.6 eV.
- the molecular weight and so the thickness of the polymer coating may be controlled by addition of free alkoxyamine (benzoate of 2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethyl up to 0.25 mmol for 5 ml of styrene) to the medium as illustrated in FIG. 6.
- free alkoxyamine benzoate of 2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethyl up to 0.25 mmol for 5 ml of styrene
- the PS chains are attached to the poly[1-acryloxy-2-phenyl-2-(2′,2′,6′,6′-tetramethyl-1′-piperidinyloxy)ethane] electrografted primer (called P in FIG.
- the polystyrene coating was confirmed by Raman spectroscopy.
- the molecular weight and so the thickness of the polymer coating can be control by addition of free initiator to the medium
- the molecular weight and so the thickness of the polymer coating may be controlled by addition of free initiator (benzyl bromide) to the medium as confirmed by Raman and SEC (FIG. 8).
- the thickness of the films reaches range between 1 to 5 m without addition of free initiator.
- Peeling test (ASTM D3330M-90) confirmed the deposition of an adherent PS coating.
- the adhesion strength is above 2340N/m. PS remains on the surface after peeling. This step is illustrated in scheme 3 step 2.
- Poly(4-acryloyloxy- ⁇ -caprolactone) (poly(ACL)) and poly(4-acryloyloxy- ⁇ caprolactone-co- ⁇ -caprolactone) (poly(ACL-co-CL)) are linear polyesters bearing pendant acryloyl groups along the polymer backbone called here macromonomers.
- the macromonomer is synthetised as described by X. Lou and al in Langmuir 2002, 18, 2785.
- DADEG dimethacrylate diethylene glycol
- the first reduction wave was already observed at a DMADEG concentration of 0.2 M.
- the coating formed at a concentration of 0.5M was thicker. At a concentration of 1 M, the first reduction wave was smaller, but the electrode passivation could be confirmed by the absence of reduction peak during a second potential scanning.
- the PEG coating was confirmed by IR-RAS with the characteristic peak of the C—O bonds at 1114 cm ⁇ 1 .
- PVC poly(vinyl chloride)
- a THF solution of PVC was spin-coated onto poly(ACL) and poly(ACL-co-CL) coatings prepared according to EXAMPLE 4.
- the PCV top coatings was confirmed by IR-RAS with the bands at 2910 and 1721 cm ⁇ 1 for alkyl and carbonyl groups adsorptions. Peeling tests (ASTM.
- D3330M-90 showed that the PVC coating was adhering strongly to poly(ACL-co-CL) (the PVC film was not removed after peeling with an adhesion strength superior to 3700N/m) but not to poly(ACL) (the PVC film was removed by peeling with an adhesion strength of 100N/m).
- Electrografting has been performed in the conditions described example 1, where ethyl acrylate has been replaced by N-acryloyloxy succinimide (concentration ranging from 0.1-3M) thus a monomer bearing a succinimidyl function as anchoring group).
- This monomer was prepared by reaction of 10 g of N hydroxysuccinimide (86.9 mmol) with 7.1 ml of acryloyl chloride (86.9 mmol) in 200 ml of dried CH 2 Cl 2 in presence of 12.1 ml of triethylamine (86.9 mmol). The reaction is performed overnight at room temperature with a yield after purification of 95%.
- the monomer structure was confirmed by RMN H (CDCl3): _(ppm): 2.84 (s, 4H, C H 2 C H 2 ), 6.14 (d, 1H, C H 2 ⁇ CH), 6.26 (q, C H CO) et 6.68 (d, 1H, C H ⁇ CH), and IR (KBr): _(cm): 3083, 3007 (C—H olefiniques), 2955 (C—H aliphatics), 1809-1777-1732 (C ⁇ O), 1405 (C—N) et 1213 (C—O).
- the adhesion energy of the coating onto steel was higher than 3070 N/m, as compared with 1850 N/m for neat steel.
- the film thickness of this primer coating is low (10 nm as determined by XPS) and weakly increased with increasing the monomer concentration from 0.1M up to 3M.
- the amino groups bear by the styrene backbone are complementary reactive groups that can react with X, the succinimidyl activated ester.
- the electrode was then heated at 150° C. under vacuum for 24 h. Unreacted polystyrene was removed by Soxhlet extraction in THF for 2 weeks.
- the FTIR-RAS spectrum of the modified electrode confirmed the deposition of polystyrene (bands at 3086, 3064, 3028, 2927 and 1601, 1487, 1444 and 1001 cm ⁇ 1 typical for styrene unit). Moreover, the grafted polystyrene film was not detached by the peeling test (ASTM D3330M-90).
- Ferrocene amine was grafted onto the polyacrylate succinimide (P in FIG. 1) by the grafting onto technique (FIG. 2 b ).
- the modified carbon or gold plates were immersed during 6 days at room temperature in 5 ml of a DMF solution containing 0.1 g of aminoferrocene (synthesized following Van Leusen D. et al, Organometallics , 2001, 20, 224-226.) and a catalytic amount of dimethylaminopyridine.
- cyclic voltammetry FIG. 10 which shows the electroactivity of the ferrocene in the anodic potential range for various scanning rates (100, 50 and 20 mV/s).
- Biotine-cadaverine (Aldrich) was grafted onto the polyacrylate succinimide (P in FIG. 1) by the grafting onto technique (FIG. 2 b ).
- FIG. 11 shows the absorbance of the coating revealed by the dye (curve a) in comparison without the dye (curve b). This spectrum was recorded by UV-VIS spectrophotometer (Hitachi U3300) using electrografted transparent substrates consisting of glass coated with a thin conducting layer of indium-tin oxide (ITO-glass).
- PCL was grafted from a PEA primer coating electrografted onto steel (20 ⁇ 10 ⁇ 1 mm-plate), as described in EXAMPLE 1.
- Three ml of a solution of PCL (10 wt %, Mo 5.8 10 3 ) and rhodamine-6G (11.2 wt %, 336 ug) in chloroform was cast onto the PEA-PCL coated plates, followed by a chloroform solution of PCL alone to cover the previous PCL with Rhodamine top coating.
- the plates were then immersed into 1 ml of phosphate buffer (0.13 M, pH 7.4) at 37° C. The whole aqueous volume was collected at regular times and replaced with fresh buffer.
- the concentration of rhodamine-6G in the aliquots was determined by fluorescence spectrometry (excitation wavelength 526 nm, emission wavelength 550 nm).
- fluorescence spectrometry excitation wavelength 526 nm, emission wavelength 550 nm.
- the PCL top coating was no longer adhering and had detached from the surface.
- low-angle IR spectroscopy revealed that the surface remained covered with PCL, probably coming from the electrografted PEA-PCL coating.
- Rhodamine-6G was released regularly from the PCL coating, with a limited burst effect at early times more likely due to the PCL top coating (FIG. 12).
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EP1425315A2 (de) | 2004-06-09 |
JP2004538132A (ja) | 2004-12-24 |
WO2002098926A3 (en) | 2003-10-16 |
AU2002317800A1 (en) | 2002-12-16 |
WO2002098926A2 (en) | 2002-12-12 |
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