WO2005058863A1 - Reaktive cyclische carbonate und harnstoffe zur modifizierung von biomolekülen, polymeren und oberflächen - Google Patents
Reaktive cyclische carbonate und harnstoffe zur modifizierung von biomolekülen, polymeren und oberflächen Download PDFInfo
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- WO2005058863A1 WO2005058863A1 PCT/EP2004/014047 EP2004014047W WO2005058863A1 WO 2005058863 A1 WO2005058863 A1 WO 2005058863A1 EP 2004014047 W EP2004014047 W EP 2004014047W WO 2005058863 A1 WO2005058863 A1 WO 2005058863A1
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- Prior art keywords
- alkyl
- compound
- oxo
- formula
- dioxolan
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- 0 O*C(CO1)OC1=O Chemical compound O*C(CO1)OC1=O 0.000 description 2
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D317/00—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms
- C07D317/08—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3
- C07D317/10—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings
- C07D317/32—Heterocyclic compounds containing five-membered rings having two oxygen atoms as the only ring hetero atoms having the hetero atoms in positions 1 and 3 not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D317/34—Oxygen atoms
- C07D317/36—Alkylene carbonates; Substituted alkylene carbonates
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D243/00—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms
- C07D243/04—Heterocyclic compounds containing seven-membered rings having two nitrogen atoms as the only ring hetero atoms having the nitrogen atoms in positions 1 and 3
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/12—Chemical modification
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31—Surface property or characteristic of web, sheet or block
Definitions
- Reactive cyclic carbonates and ureas for the modification of biomolecules, polymers and surfaces
- the present invention relates to a process for modifying substrates such as biomolecules, polymers and surfaces having reactive cyclic carbonates and ureas, as well as cyclic carbonates and ureas, and modified polymers.
- material surfaces can be rendered biocompatible by coating with heparin.
- Other applications include antisoiling and bacteriostatic finishing and improving the adhesion of adhesives and paints.
- the modification of a surface can take place either reactively by formation of covalent bonds or by chemisorption or adsorption.
- a reactive modification are those with isocyanates, with silanes and by radical grafting reactions.
- One frequently used method for introducing functional groups onto surfaces makes use of the coating with functional silanes, in particular aminosilanes.
- the treatment with aminosilanes is technically complicated and can not take place from aqueous solution.
- Chemisorption is based on ionic interactions between negative surface charges and cationic compounds, e.g. B. ammonium compounds. On the surface of almost all materials one finds negatively charged groups.
- cationic compounds such as the polyolefins
- negative surface charges are formed by oxidation in air; this can be artificially enhanced by a plasma treatment or UV oxidation.
- Polycationic polymers such as polyammonium compounds, adsorb onto such surfaces through polyelectrolyte complex formation. The cooperativity of multiple ion pairing gives rise to a very strong bond, which is stable even at high ionic strengths and extreme pH values.
- the targeted modification of biomolecules is desirable in many cases.
- the biological half-life of various drugs can be improved, for example, by adding polyoxyalkylene radicals.
- WO 02/42383 describes radiation-curable compositions which may contain 2-0x0-1, 3-dioxolan-4-yl-methoxycarbonylaminoethyl acrylate.
- the invention in a first aspect relates to a process for modifying a substrate having functional groups selected from hydroxy, primary and secondary amino groups by contacting at least one substrate under conditions with a compound of formula I or II in that the functional groups react with the opening of the 1,3-dioxolane ring or 1,3-diazaheptane ring and form a covalent bond with the compound of the formula I or II,
- X represents (i) the residue of a polyamine to which the parenthesized formula portion is attached via (CO) NH groups, or (ii) a polymeric backbone, to which the parenthetical formula part is attached via (CO), NH-C 2 -C 6 -alkylene-O (CO) - or (CO) -O-C 2 -C 6 -alkylene-O (CO) - groups is.
- k is 1 or an integer greater than 1, e.g. 2 or 3, or 2 - 10000, such as 10 - 1000.
- the substrate is preferably a biomolecule, polymer or surface.
- the compound of the formula I or II is brought into contact with a first substrate under conditions such that a covalent bond is formed between a first end of the compound of the formula I or II and the first substrate, and brings about this Reaction product with a second substrate under conditions that forms a covalent bond between a second end of the compound of formula I or II and the second substrate.
- the radical X generally comprises a functional group capable of reacting with the first substrate, preferably a (meth) acryloyl, aryloxy, vinylsulfonyl or haloalkyl group.
- the first and second substrates are z. In pairs a surface and a biomolecule, a biomolecule and a modifier or a surface and a modifier.
- a modifier may be a low molecular weight or polymeric compound that imparts certain hydrophilic or lipophilic properties, solubility, stability or the like, or a directing molecule.
- the invention relates to compounds of the general formula I or II
- X represents the remainder of a polyamine to which the parenthesized part of the formula is linked via (CO) NH groups.
- polyamines are alkylenediamines, dialkylenetriamines, polydimethylsiloxanes having aminoalkyl groups (terminal or as side groups), polyvinylamine, polyallylamine, polyethyleneimine, chitosan, polyamide-epichlorohydrin resins, polyaminostyrene, peptides or proteins.
- alkyl is intended to include straight-chain, branched and cyclic alkyl groups having from 1 to 30, preferably 1 to 18, in particular 1 to 12 carbon atoms.
- aryl preferably means phenyl or naphthyl which is optionally substituted with 1 to 3 CC 4 alkyl or C 1 -C 4 alkoxy groups.
- haloalkyl means an alkyl group in which one or more or all of the hydrogen atoms are replaced by halogen, especially fluorine.
- hydroxyalkyl means an alkyl group in which one or more hydrogen atoms are replaced by hydroxy groups.
- alkyloxyalkyl mean an alkyl radical in which one or more hydrogen atoms an alkyloxy group, an alkylcarbonyloxy group, an amino group, an ammonium O group (NR 3 3 +,.
- each R 3 independently eg for dC 18 alkyl or benzyl), an acryloyloxy group Polyoxyalkenylrest, a Polysiloxanylrest, a (meth) a sulfonic acid group (SO 3 H), a phosphonic acid group (PO 3 H 2 ) or phosphoric acid ester group (OPO 3 H 2 ) are replaced.
- R 1 is ammonioalkyl
- the compound is one equivalent of an anion, preferably a physiologically acceptable anion, such as a halide, e.g. As chloride or bromide, sulfate, hydrogen sulfate, methosulfate, nitrate or the like.
- the polyoxyalkylene radical is preferably derived from ethylene oxide and / or propylene oxide, in particular from ethylene oxide. It can be terminated at the distal end, for example by a hydroxy, alkyloxy or alkaryloxy group.
- the polysiloxanyl radical is preferably derived from polydimethylsiloxanes.
- the saccharide residue is, for. B. to a Glucosylrest.
- biomolecule includes all molecules that are isolated from biological systems and / or that can interact with biological systems or parts thereof. These include, in particular, peptides, proteins, proteoglycans, enzymes, markers, antibodies, receptor molecules, antigens, active substances. Specific examples are heparin, tissue plasminogen activator, streptokinase, prostaglandins and the like.
- R 1 is - (CH 2 ) n -CH 3 ,
- R 2 is CC 18 alkylene
- R 3 is C -C 8 alkyl or benzyl
- R 4 is hydrogen or methyl
- Y represents one equivalent of an anion such as those mentioned above, n and m independently represent an integer of 0 to 12; and p is an integer of 1 to 100, preferably 2 to 50.
- the compounds can be prepared in various ways using standard methods of organic synthesis. Preferred modes of preparation are illustrated in the examples.
- Compounds of the formula I in which X is a polymeric skeleton can be prepared by free-radical polymerization or controlled radical polymerization, for.
- ATRP Atom Transfer Radical Polymerization
- Comonomers are preferably used here, such as C 1 -C 4 -alkyl acrylates, in particular methyl (meth) acrylate, and / or vinylaromatics, such as styrene.
- comonomers are also used which have nucleophile-reactive side groups and whose reactivity is different from that of the 2-oxo-1,3-dioxolanyl radical.
- a preferred reactive comonomer is 2-phenoxycarbonyloxyethyl (meth) acrylate.
- a preferred compound of formula I wherein X is a polymeric backbone is a copolymer of 2-oxo-1,3-dioxolan-4-ylmethyl (meth) acrylate, 2-phenoxycarbonyloxyethyl (meth) acrylate and methyl (meth) acrylate.
- nucleophiles e.g. Hydroxy or amino groups of biomolecules or polymers or on substrate surfaces
- R ring opening and formation of a covalent bond
- the compounds of the invention allow to introduce a wide range of different radicals X in biomolecules or polymers or bind to substrate surfaces.
- Surfaces that can be treated by this method are e.g., the surfaces of materials having intrinsic amino and / or hydroxy groups, or surfaces which have been treated with aminosilanes according to known methods.
- the invention further provides modified polymers, ie reaction products of the compounds according to the invention with a polymer which has functional groups selected from hydroxy groups, primary and secondary amino groups.
- the reaction of the compounds according to the invention with a polyamine or a polyol allows the introduction of the functional group X into the polymer structure.
- polyamines are polyvinylamine, polyallylamine, polyethylenimine, chitosan, polyamide-epichlorohydrin resins, such as those sold under the name Hercosett®, polyaminostyrene, peptides or proteins, such as gelatin.
- Preferred proteins are modified keratin polypeptides enriched by reverse proteolysis (Plastein reaction) with lysine (2,6-diaminohexanoic acid).
- the reaction of the polymer with the compounds according to the invention is a polymer-analogous reaction.
- the concentration of the functional groups X in the reaction product can be adjusted by selecting the stoichiometric ratio of the amino or hydroxyl groups in the polymer to the reagent I or II.
- At least some of the radicals R 1 are ammonioalkyl, ie the reaction products are cationic polyelectrolytes.
- the resulting cationic polyelectrolytes can adhere permanently to an anionic material surface by polyelectrolyte interaction.
- the reaction is carried out so that not all hydroxy and / or amino groups of the polymer participate in the reaction with the compounds according to the invention, so that the reaction products still contain reactive hydroxyl and / or primary or secondary amine functions.
- reactive NH 2 -, NH- or OH groups can be introduced into the surfaces, which allow a fast and effective connection of different coatings. Examples are epoxides, isocyanates, anhydrides and carboxylic acids, as well as acrylates (Michael addition), but also drugs of any kind can be immobilized on the surface in this way.
- part of the radicals R 1 is ammonioalkyl, and part of the radicals R 1 is one or more radicals which are different therefrom.
- the reaction product possesses, in addition to the cationic groups which serve for attachment / adhesion to a material surface, further functional groups. These can be used to anchor different functional groups on a surface.
- biomolecules such as drugs, eg. B. bactericides, insecticides or medicaments, which may become active only after hydrolytic or enzymatic degradation by release.
- the invention relates to a process for modifying surfaces, in which the surface is brought into contact with a reaction product described above, in particular one in which at least part of the radicals R 1 is ammonioalkyl.
- the surfaces which may be treated in this way may be those of any materials, e.g. As glass, ceramic materials, metals, plastics such as polyolefins, polystyrenes, impact modified polystyrenes. It is also possible to treat the surfaces of fibers or filaments. It is a particular advantage of the invention that the coating or the application of the reaction product can be carried out from an aqueous solution and does not require any complicated preparation and equipment, for example surface treatment with aminosilanes.
- FIG. 1 shows schematically the production of a modified polycationic material surface according to the invention.
- A denotes the compound of the formula I used according to the invention (in which R denotes, for example, -CH 2 -OCONH- (CH 2 ) 3 - and Hg "represents a halide) with an ammonium substituent the polyamine
- B leads to the reaction product (C).
- C shows a material surface with negative surface charges Z ' , which are loosely associated with cations Mt + , treating the material surface (D) with the reaction product (C) Salt Mt + Hlg " displaced and it forms a strong adhesion of the polymer to the surface due to the multiple ion pair interaction.
- Amine groups (-NH 2 ) are available on the polymer for further modifications.
- the compound can be obtained according to the procedure described by J.F.G.A. Jansen, A.A. Dias, M. Dorschu, B. Coussens, Macromolecules 2003, 36, 3861-3873.
- Type i Type II In a suitable size flask fitted with reflux condenser and adjustable stirrer, add one of the components C listed in Table 1 in the stated amount (in equivalents) at the indicated temperature with stirring to an initially introduced solution of component A.1 or A. .2 (for the preparation of further compounds of the formula I) or component B (for the preparation of further compounds of the formula II) in a suitable solvent (for example chloroform, dichloromethane, ethyl acetate, dimethyl sulfoxide, dimethylacetamide, dimethylformamide). The solution is then stirred for the time indicated in Table 1. The product is isolated by conventional methods (distilling off the volatiles, precipitates and / or chromatography).
- a suitable solvent for example chloroform, dichloromethane, ethyl acetate, dimethyl sulfoxide, dimethylacetamide, dimethylformamide
- the residue is taken up with 200 ml of a mixture of THF / Et 2 O (1: 1) and extracted 5 times with 50 ml of H 2 O each time.
- the combined aqueous phases are extracted 5 times with 70 mL CHCl 3 each time.
- the organic phase is dried over Na 2 SO 4 , the desiccant is filtered off and the solvent is distilled off by means of a rotary evaporator.
- the colorless, highly viscous oil is dried overnight with stirring in the HV.
- dicarbonate A.1 (2.00 g, 8.40 mmol) was dissolved in 20 mL of dry THF. After cooling to 0 ° C, a suspension of dodecylamine (1.56 g, 8.40 mmol) in 10 mL dry THF was added slowly and the temperature kept below 5 ° C and allowed to warm to RT overnight. The solvent was removed under vacuum (-20 mbar, 40 ° C). The cyclic carbonate functionalized with a C 12 alkyl chain was dissolved in 15 mL CHCI 3 and crystallized by the addition of 30 mL Et 2 O. (Yield: 93%).
- dicarbonate A.1 (5.00 g, 21.0 mmol) was dissolved in 20 mL of dry THF and cooled to 0 ° C.
- the reaction was stirred at 0 ° C for 2 hours and at RT for 1.5 days.
- the solvent was removed under vacuum (-20 mbar, 40 ° C).
- the functionalized with a C 18 alkyl chain cyclic carbonate was recrystallized from CHCl 3 . (Yield: 85%).
- the compound was prepared analogously to compound 1.1, using the compound fertil A.2 instead of the compound A.1 as starting material.
- the compound was prepared analogously to compound I.3, using compound A.2 instead of compound A.1 and hexylamine instead of butylamine as starting materials.
- the compound was prepared analogously to compound I.4, using compound A.2 as starting material instead of compound A.1.
- the compound was obtained by reacting 14.7 mmol of compound 1.2 with 29 mmol of dimethyl sulfate in 90% yield.
- the compound was prepared analogously to the compound I.6, using the compound 1.7 instead of the compound 1.1 as starting material.
- the compound was prepared analogously to compound 1.12, using compound A.2 as the starting material instead of compound A.1.
- one of the components D listed in Table 2 which corresponds to one of the components C or is a nitrogen-containing polymer or a polyol, is added in the stated amount (in equivalents) to the number of functional groups in the polymer) at the indicated temperature with stirring to a solution of a compound of formula I or II in a suitable solvent (eg, water, chloroform, dichloromethane, ethylacetate, dimethylsulfoxide, dimethylacetamide, dimethylformamide).
- a suitable solvent eg, water, chloroform, dichloromethane, ethylacetate, dimethylsulfoxide, dimethylacetamide, dimethylformamide.
- Example 2.1 Reaction of 1.12 with dimethylaminopropylamine To a solution of 6.27 g of compound 1.12 in 50 ml of THF, a solution of 0.78 g (7.7 mmol) of dimethylaminopropylamine in 10 ml of THF is added dropwise at 66.degree. To complete the reaction, the reaction solution is refluxed for an additional 72 hours. After removal of the solvent, a dark yellow viscous oil is obtained.
- Example 2.2 Reaction of 1.13 with dimethylaminopropylamine The reaction and quaternization were carried out analogously to Example 2.1.
- Example 2.3 Reaction of 1.1 with nonadimethylsiloxanedipropylamine
- Example 2.6 Reaction of 1.5 with dimethylaminopropylamine
- the cyclic carbonate functionalized with a C 18 -alkyl chain (2.50 g, 6.04 mmol) and 3-dimethylaminopropylamine (0.74 g, 7.25 mmol) were dissolved in 25 mL CHCl 3 and stirred under reflux for 20 hours. The solvent was removed in vacuo and the functional diurethane was used without further purification for the quaternization of the amino group. (Yield: quantitative).
- Example 4.1 Copolymerization of 2-oxo-1,3-dioxolan-4-yl-methyl methacrylate and methyl methacrylate
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Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/582,053 US7728069B2 (en) | 2003-12-09 | 2004-12-09 | Reactive cyclic carbonates and ureas used for modifying biomolecules, polymers, and surfaces |
ES04801220T ES2395414T3 (es) | 2003-12-09 | 2004-12-09 | Carbonatos y ureas cíclicos reactivos para modificar biomoléculas , polímeros y superficies |
PL04801220T PL1692126T3 (pl) | 2003-12-09 | 2004-12-09 | Reaktywne, cykliczne węglany i moczniki do modyfikacji cząsteczek biologicznych, polimerów i powierzchni |
JP2006543482A JP4866738B2 (ja) | 2003-12-09 | 2004-12-09 | 生体分子、ポリマー及び基材表面の変性に使用される反応性環状カーボネート及び尿素 |
EP04801220A EP1692126B1 (de) | 2003-12-09 | 2004-12-09 | Reaktive cyclische carbonate und harnstoffe zur modifizierung von biomolekülen, polymeren und oberflächen |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
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EP03028224A EP1541568A1 (de) | 2003-12-09 | 2003-12-09 | Reaktive cyclische Carbonate und Harnstoffe zur Modifizierung von Biomolekülen, Polymeren und Oberflächen |
EP03028224.8 | 2003-12-09 |
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WO2005058863A1 true WO2005058863A1 (de) | 2005-06-30 |
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PCT/EP2004/014047 WO2005058863A1 (de) | 2003-12-09 | 2004-12-09 | Reaktive cyclische carbonate und harnstoffe zur modifizierung von biomolekülen, polymeren und oberflächen |
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US (1) | US7728069B2 (de) |
EP (2) | EP1541568A1 (de) |
JP (1) | JP4866738B2 (de) |
ES (1) | ES2395414T3 (de) |
PL (1) | PL1692126T3 (de) |
WO (1) | WO2005058863A1 (de) |
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Also Published As
Publication number | Publication date |
---|---|
EP1692126A1 (de) | 2006-08-23 |
PL1692126T3 (pl) | 2013-04-30 |
JP4866738B2 (ja) | 2012-02-01 |
US7728069B2 (en) | 2010-06-01 |
JP2007523057A (ja) | 2007-08-16 |
US20070092656A1 (en) | 2007-04-26 |
ES2395414T3 (es) | 2013-02-12 |
EP1692126B1 (de) | 2012-11-07 |
EP1541568A1 (de) | 2005-06-15 |
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