WO2008064887A1 - Dérivé de bislactamide comme composé intermédiaire dans la production de diisocyanate - Google Patents

Dérivé de bislactamide comme composé intermédiaire dans la production de diisocyanate Download PDF

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Publication number
WO2008064887A1
WO2008064887A1 PCT/EP2007/010356 EP2007010356W WO2008064887A1 WO 2008064887 A1 WO2008064887 A1 WO 2008064887A1 EP 2007010356 W EP2007010356 W EP 2007010356W WO 2008064887 A1 WO2008064887 A1 WO 2008064887A1
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Prior art keywords
compound
diisocyanate
formula
polymer
article
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PCT/EP2007/010356
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English (en)
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WO2008064887A8 (fr
Inventor
Aylvin Jorge Angelo Athanasius Dias
Bartholomeus Johannes Margretha Plum
Jacobus Antonius Loontjens
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Dsm Ip Assets B.V.
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Publication of WO2008064887A1 publication Critical patent/WO2008064887A1/fr
Publication of WO2008064887A8 publication Critical patent/WO2008064887A8/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C263/00—Preparation of derivatives of isocyanic acid
    • C07C263/08—Preparation of derivatives of isocyanic acid from or via heterocyclic compounds, e.g. pyrolysis of furoxans
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
    • A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
    • A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
    • A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
    • A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
    • A61L27/14—Macromolecular materials
    • A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D201/00—Preparation, separation, purification or stabilisation of unsubstituted lactams
    • C07D201/02—Preparation of lactams
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/02—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom not condensed with other rings
    • C07D223/06—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom 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
    • C07D223/08—Oxygen atoms
    • C07D223/10—Oxygen atoms attached in position 2
    • 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
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P20/00—Technologies relating to chemical industry
    • Y02P20/50—Improvements relating to the production of bulk chemicals
    • Y02P20/55—Design of synthesis routes, e.g. reducing the use of auxiliary or protecting groups

Definitions

  • This invention relates to a compound from which a diisocyanate can be made and to a method for preparing the compound.
  • the present invention further relates to a method for preparing a diisocyanate, to a method for preparing a polymer from the diisocyanate, and to a method for preparing a shaped article comprising such polymer, in particular an implantable article.
  • Diisocyanates are compounds which can be polymerised with polyols, such as diols, to form polyurethanes.
  • Polyurethanes may be used in various applications, e.g. in coatings, thermal insulation articles, adhesives, wheels, furniture, car components or construction sealants.
  • Polyurethanes may also be used in medical applications, e.g. as described in WO 2004/074342. These applications include medical coatings and bulk plastic medical devices such as catheters, leads for pacemaker, tubing, hospital bedding, surgical drapes, wound dressings, as well as in a variety of injection moulded devices and short-term implants. Polyurethanes are widely used because of their wide range of physical properties and biological properties. These are toughness and flexibility to biocompatibility, and hemocompatibility.
  • polyurethane in a medical application requires the polymer to have a low as possible toxicity.
  • a common way of preparing a diisocyanate involves the phosgenation of a diamine in a suitable solvent.
  • phosgene is poisonous and presents certain handling risks. This is particularly in cases wherein a small volume of a specialised medical grade polurethane is prepared. Accordingly, the manufacturing process is potentially hazardous.
  • DE 196 27 552 describes the preparation of an organic polyisocyanate by reacting polyamine and a carbamide acid ester or urea, to provide a monomeric polyurethane and thermally cleave the polyurethane to obtain the polyisocyanate and an alcohol.
  • the reaction is carried out in the presence of a catalyst and at a temperature of up to 250 0 C to carry out the cleaving within an economically advantageous time-span.
  • the invention relates to a compound represented by formula I H H O
  • Y is selected from CH(OX) or CH(COOX); o and p each are an integer of 0-4, with the proviso that the sum of o and p is 4 or less, preferably 2, 3 or 4; X is a protective group; and each L is a lactam, which may be the same or different.
  • the invention relates to a method for preparing the intermediate compound for a diisocyanate, comprising reacting a diamine represented by the formula H 2 N-(CH 2 ) O -Y-(CH 2 ) P -NH 2 , wherein Y, o and p are as identified above, with a carbonylbislactam, preferably carbonylbiscaprolactam, thereby forming a compound with formula I, wherein L is a lactam from the carbonylbiscaprolactam.
  • the invention provides a compound and a method to prepare such a compound which is suitable for safely preparing a diisocyanate, without requiring the use of a highly toxic reagent such as phosgene or HNCO or a highly explosive reagent such as an azide.
  • the invention further provides a compound and a method to prepare such a compound which is suitable for preparing a diisocyanate, without the formation of undesired side products.
  • a diisocyanate can be formed from a compound represented by formula I, whilst cyclisation reactions are avoided or at least reduced, compared to a known method, in particular a method wherein the diisocyanate is prepared from by phosgenation of the diamine.
  • a known method in particular a method wherein the diisocyanate is prepared from by phosgenation of the diamine.
  • the compound of formula I may be used in the preparation of a polymer, especially a polymer of medical grade.
  • Preferred application areas include polymers for implantable articles, such as bone substitutes; cartilage substitutes; vascular substitutes, for instance grafts; housing for implantable devices, for instance pacemakers; and tubing, catheters and drains; medical coatings; leads for pacemaker; hospital bedding; surgical drapes, wound dressings; injection moulded devices; porous implantable articles, tissue engineering and short-term implants.
  • a preferred example of a cartilage substitute is an artificial meniscus. Accordingly, the invention further relates to a compound represented by formula I in the manufacture of an implantable article for treating a malfunctioning body part, in particular a malfunctioning joint, more in particular a malfunctioning knee.
  • the compound of formula I may in principle be made from any diamine, having two primary amines, meeting the above definition for -(CH 2 ) 0 -Y- (CH 2 ) P -.
  • Moiety Y providing a carboxylic acid or a hydroxyl functional group which is preferably protected, in view of the synthesis of the compound with formula I and/or in view of its further use such as in the preparation of a diisocyanate (see Formula II, below).
  • Suitable protective groups include protective hydrocarbons, such as phenyl and alkyls, in particular C1-C4 alkyls, such as methyl, ethyl, propyl, n-butyl, t- butyl; oxazines; oxazolines; imidazole, t-butyloxycarbonyl groups and protective organo-silicon compounds, such as Si(OR) 3 and SiR 3 , wherein R is a hydrocarbon group, in particular a hydrocarbon selected from phenyl and alkyls, more in particular a C1-C4 alkyl, as mentioned above.
  • R is a hydrocarbon group, in particular a hydrocarbon selected from phenyl and alkyls, more in particular a C1-C4 alkyl, as mentioned above.
  • suitable diamines are in particular lysine provided with a protective group or ornithine provided with a protective group.
  • the diamine is preferably a natural diamine chosen from lysine and ornithine. Lysine has been found particularly suitable to prepare a diisocyanate for the preparation of a polyurethane from which an implant, especially an artificial meniscus, may be manufactured.
  • a natural diamine is in particular preferred in case the implant is biodegradable, because as the implant degrades, the diamine may be released into the body.
  • the term "natural” is in particular used herein as being naturally present in a human body.
  • the diamine may in principle be reacted with any carbonylbislactam.
  • the lactam ring comprises 4-16 carbon atoms, including the carbon from the carbonyl.
  • the lactam ring comprises 6 carbon atoms, including the carbon from the carbonyl group.
  • the reaction of the diamine and the carbonylbislactam can take place in a melt of the reaction components or in a suitable solvent.
  • suitable solvents include aromatic solvents, e.g. toluene, xylene; esters, in particular formiate esters and acetate esters, more in particular ethylacetate; halogenated alkanes, e.g. chloroform; aliphatic alcohols, e.g. methanol, ethanol, a propanol; and mixtures thereof.
  • esters such as ethyl acetate
  • An ester such as ethyl acetate
  • amines and esters may react with each other.
  • Advantages of esters, such as ethyl acetate, include low toxicity and the ease of removal from the product.
  • the molar ratio diamine:carbonylbislactam usually is at least about stoichiometric, i.e. at least about 2:1.
  • the reaction temperature may be chosen within wide limits. Usually the temperature is less than 150 0 C, to avoid undesirable levels of side reactions. Preferably, the reaction temperature is 125 0 C or less, in particular 100 0 C or less.
  • the temperature is usually higher than 25 °C, preferably at least 50 0 C, in particular at least 60 C C, more in particular at least 80 0 C to reduce reaction time.
  • the reaction time may suitably be chosen, depending upon the reaction temperature, desired yield and one or more optionally present aids, such as a catalyst.
  • a suitable catalyst may for instance be chosen from the group consisting of acids and bases, including Lewis acids and Lewis bases.
  • acids including Lewis acids
  • Lewis acids that are suitable as a catalyst are LiX 1 Sb 2 O 3 , GeO 2 en As 2 O 3 ,BX 31 MgX 2 , BiX 3 , SnX 4 , SbX 51 FeX 3 , GeX 4 , GaX 31 HgX 2 , ZnX 21 AIX 3 JiX 41 MnX 2 , ZrX 4 , R 4 NX 1 R 4 PX 1 HX 1 wherein X is selected from the group consisting of I, Br 1 CI, F 1 OR, acetylacetonate and compounds with the formula
  • R and R' are independently selected from the group consisting of alkyl, aryl, alkoxy and aryloxy.
  • Br ⁇ nstedt acids such as H 2 SO 4 , HNO 3 , HI, HCI, HBr, HF, H 3 PO 4 ,
  • R represents an alkyl or aryl, in particular C1- C20 alkyl or aryl.
  • DABCO diazabicyclo [2,2, 2] octane
  • DMAP dimethylaminopyridine
  • guanidine morpholine.
  • reaction time will usually be at least about 1 hour, more in particular at least 2 hours.
  • the diamine comprises a protected functional group ⁇ i.e. Y is present
  • a reaction time of at least 6 hours, at least 24 hours, or at least 36 hours may be preferred, for improved conversion.
  • reaction time 24 hours or less, in particular of 12 hours or less, more in particular of 2 hours or less.
  • a longer reaction time may be desired for improved conversion, for instance the reaction may be continued for up to 24 hours, for instance up to 36 hours or even for 60 hours or more.
  • the compound with formula I obtained from the above described reaction may be purified, e.g. by recrystallisation.
  • This diisocyanate may be represented by formula Il
  • the diisocyanate is suitably made by heating the compound represented by Formula I to a suitable temperature.
  • the formation of the diisocyanate may be carried out in the presence of a catalyst.
  • Suitable catalysts include those described in K. Frisch, Advances in Urethane Science and Technology, vol 1 (1971), p 1-30.
  • Specific examples include dialkyl tin oxides, such as dibutyl tin oxide, and tetraalkyltitanate, such as tetrabutyl titanate. This may in particular be advantageous in case the protective group X has been removed.
  • a desired temperature depends to some extent on the lactam. Usually a temperature above 150 0 C is used, preferably a temperature of 160 0 C or more. It is envisaged that a lower temperature may be sufficient, in particular in case the reaction is carried out in the presence of a suitable catalyst, such as a tin catalyst. In an effort to avoid undesired side reactions such as polymerization of the formed diisocyanate, the temperature is usually 225 0 C or less. Preferably, the temperature is 215 0 C or less, in particular 200 0 C or less, more in particular 180 0 C or less.
  • reaction time may be chosen within suitable limits, e.g. in the range of about 1 min. to about 3 hours.
  • the diisocyanate may be purified, e.g. by distillation. At least the removal of the lactam (originating from the carbonylbislactam) preferably takes place above 150 0 C, in particular up to 225 0 C more in particular up to 200 0 C. Alternatively, the product to be purified is rapidly cooled to about 25 0 C or less, after which the diisocyanate is isolated.
  • purification may comprise extraction with water or an aqueous solution - which may comprise an agent to increase the solubility of caprolactam in water, in particular CaCI 2 - whereby caprolactam is removed from the crude product. Subsequently, unreacted blocked isocyanate may be separated from the diisocyanate by distillation.
  • the protective group may be removed from the diisocyanate, if desired. In particular, it may be removed before or after polymerizing the diisocyanate. Preferably it is removed after the polymerisation. After it has been deprotected, the functional group may be used to couple an active agent to the compound. The protective group may be removed by a chemical route.
  • the active agent may in principle being any agent having a specific functionality.
  • the active agent may be selected from pharmaceuticals, stabilisers, antithrombotic moieties and moieties increasing hydrophilicity or moieties increasing hydrophobicity.
  • the active agent may for instance be selected from cell signalling moieties, moieties capable of improving cell adhesion to the compound/polymer/article, moieties capable of controlling cell growth (such as stimulation or suppression of proliferation), antithrombotic moieties, moieties capable of improving wound healing, moieties capable of influencing the nervous system, moieties having selective affinity for specific tissue or cell types and antimicrobial moieties.
  • the moiety may exert an activity when bound to the remainder of the compound/polymer/article and/or upon release therefrom.
  • active agents examples include perfluoralkanes (increasing hydrophobicity); polyalkylene oxides, such as polyethylene oxide and polypropylene oxide (increasing hydrophilicity and/or for reduced fouling); polyoxazolines; amino acids; peptides, including cyclic peptides, oligopeptides, polypeptides, glycopeptides and proteins, including glycoproteins; nucleotides, including mononucleotides, oligonucleotides and polynucleotides; and carbohydrates.
  • an amino acid may be linked for stimulating wound healing (arginine, glutamine) or to modulate the functioning of the nervous system (asparagine).
  • the bioactive moiety is a peptide, more preferably an oligopeptide. Peptides or epitopes with specific functions are known in the art and may be chosen based upon a known function. For instance, the peptide may be selected from growth factors and other bioactive peptides.
  • the diisocyanate obtained in accordance with the invention may be used to prepare a polymer, for instance a polyurethane, a polyamide, a polythio- urethanes or a polyurea.
  • a polymer for instance a polyurethane, a polyamide, a polythio- urethanes or a polyurea.
  • Suitable polymerisation techniques are known in the art.
  • the diisocyanate may be polymerised together with one or more polyols.
  • the polyol may be a monomeric or a polymeric polyol.
  • Suitable monomeric polyols include glycerol and C1-C6 diols, such as 1 ,2-ethane diol, 1 ,2-propane diol, 1 ,3-propane diol, 1 ,4-butane diol, neopentyldiol, cyclohexyldiol and butene diol.
  • Suitable polymeric polyols include polyalkylene oxides, polymers comprising one or more polyalkylene oxide segments and at least one other segment, polyester polyols, and polymers comprising one or more polyester polyol segments and at least one other segment.
  • Preferred polymeric polyols include polyethylene oxide, polypropylene oxide, polytetramethylene oxide, polyester diols, polycarbonate diols, ⁇ , ⁇ - hydroxypolybutadiene, polyurethane diols, and copolymers thereof.
  • Preferred polyamines include polyoxyalkyleneamines, in particular amine terminated polyakylene glycols, such as of an polyalkylene glycol mentioned above.
  • Commercially available are inter alia amine- terminated polypropylene oxides and amine-terminated polyethylene oxides, e.g. under the trademark Jeffamine®.
  • Compositions comprising monomeric or polymeric diols and monomeric or polymeric diamines can be used as well.
  • the polymerization with a compound having one or more unsaturated carbon-carbon bonds may in particular be advantageous in case the polymer is to be cross-linked.
  • the polymer, such as a polyurethane, prepared according to the invention may in particular be a segmented polymer.
  • the segments chosen allow a wide variety of properties which may be tailored.
  • the polyurethane may comprise one or more soft segments that provide flexibility and one or more hard segments that provide strength.
  • a segmented polyurethane may in particular be prepared by a method for preparing a polyurethane wherein a macrodiol, a diisocyanate and a chain extender, the chain extender comprising a (cyclo) aliphatic diol, are used, comprising: a) reacting either the macrodiol or the chain extender with an excess of diisocyanate, resulting in a macrodiisocyanate or a reaction product of the diisocyanate and the chain extender, b) removing the remaining unreacted diisocyanate, c) reacting, the macrodiisocyanate with the chain extender or the macrodiol with the reaction product, wherein a) and c) are carried out in the substantial absence of a catalyst.
  • porous articles are often made by blending the polymer (or the starting materials that are to be polymerised) with a matrix material for forming the pores (such as a sugar or a salt), which matrix material is washed out after the article is formed, removal of caprolactam may be accomplished without needing an extra reaction step.
  • a matrix material for forming the pores such as a sugar or a salt
  • removal of caprolactam may be accomplished without needing an extra reaction step.
  • the preparation of an article, such as a porous implant by directly polymerising the compound of formula I may be advantageous in that a reaction step (deblocking the blocked isocyanate moieties) may be omitted.
  • the polymerisation may take place in a mould, such that a shape article is formed, as the polymer is formed or first the polymer may be made from which - if desired - the shaped article may be formed. Suitable techniques are known in the art.
  • the polymer in particular the polyurethane, can be processed using extrusion, injection moulding, film blowing, solution dipping, and/or two-part liquid moulding.
  • a porous material may be formed, for instance in an implant to allow in-growth of cells or even vasculature.
  • a porous material may for instance be formed by
  • Removal may for instance be accomplished by contacting the solid polymer with a liquid that is a solvent for the particulate matter but not for the polymer.
  • a method for making a porous scaffold from the polymer comprising: a) providing a homogeneous solution of the polymer in a solvent wherein the polymer-solvent combination is chosen in such a way that for the chosen combination liquid-liquid phase separation occurs, upon cooling down, at a temperature (TNq) that is higher than the crystallization temperature of either the polymer (Tc 1 p) or the solvent (Tc, s), b) adding a particulate material that is insoluble in the solvent, c) cooling down the mixture obtained in b) at a rate that allows liquid-liquid phase separation to result in the desired micropore morphology for the porous scaffold, to a temperature below the crystallization temperature of either the polymer (Tc, p) or the solvent (Tcfs) d) washing the mixture obtained in c) with a non-solvent, wherein
  • the polymer prepared according to the invention such as a polyurethane may be used to provide a coating, which can be hydrophilic or hydrophobic. It can be used to provide an antimicrobial, non-thrombogenic, drug releasing, and/or lubricious coating.
  • One or more biological functions may be provided in combination with specific physical properties such as toughness, strength and/or abrasion resistance.
  • the polymer may be advantageously used in a drug-eluting stent coating.
  • Patients having bare-metal stents have a high rate of restenosis, or blockage.
  • Specific drugs that can lower the restenosis rate may be incorporated into the polyurethane matrix and gradually released once the stent is in place. Drug-release rates are controlled by the ratio of the hard-segment to soft-segment content of the polymer and the specific chemistry.
  • Another useful property for coating of a polymer, in particular a polyurethane, prepared according to the invention is its ability to stretch conformally with to the metal stent when the stent is deployed and expanded such that the coating must no delaminate, tear or break.
  • a capillary nitrogen flow

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Veterinary Medicine (AREA)
  • General Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Animal Behavior & Ethology (AREA)
  • Hematology (AREA)
  • Materials Engineering (AREA)
  • Engineering & Computer Science (AREA)
  • Dermatology (AREA)
  • Medicinal Chemistry (AREA)
  • Oral & Maxillofacial Surgery (AREA)
  • Transplantation (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un procédé de préparation d'un composé intermédiaire pour un diisocyanate. Ledit procédé comprend l'étape consistant à faire réagir une diamine de formule H2N-(CH2)0-Y-(CH2)p-NH2, Y étant choisi parmi CH(OX) ou CH(COOX), o et p étant chacun un nombre entier de 0 à 4, à condition que la somme o plus p vaille 4 ou moins, de préférence 2, 3 ou 4, et X étant un groupe protecteur, avec un carbonylbislactame, de préférence un carbonylbiscaprolactame, ladite réaction permettant de former un composé de formule (I) dans laquelle chaque L est un lactame provenant du carbonylbislactame.
PCT/EP2007/010356 2006-11-29 2007-11-29 Dérivé de bislactamide comme composé intermédiaire dans la production de diisocyanate WO2008064887A1 (fr)

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EP06024728.5 2006-11-29
EP06024728 2006-11-29

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WO2008064887A8 WO2008064887A8 (fr) 2008-09-04

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Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1905098A1 (de) * 1969-02-01 1970-08-13 Bayer Ag Verfahren zur Herstellung von Polyamiden
DE2250134A1 (de) * 1972-10-13 1974-04-25 Cassella Farbwerke Mainkur Ag Verfahren zur herstellung von substituierten harnstoffen
US4374771A (en) * 1982-03-08 1983-02-22 American Cyanamid Company Blocked isocyanate
JPS61171732A (ja) * 1985-01-23 1986-08-02 Unitika Ltd 高重合度ポリアミドの製造法
WO2003061722A2 (fr) * 2002-01-23 2003-07-31 Scimed Life Systems, Inc. Dispositifs medicaux employant des polymeres a chaine etendue
WO2003070785A1 (fr) * 2002-02-21 2003-08-28 Dsm Ip Assets B.V. Procede de preparation de polymeres fonctionnalises et de produits intermediaires, compositions et parties faconnees
WO2004074342A1 (fr) * 2003-02-19 2004-09-02 Orteq B.V. Procede de preparation de nouveaux polyurethannes segmentes presentant des resistances elevees a la dechirure et a la traction et procede de production de greffes poreuses servant de support
WO2005094757A1 (fr) * 2004-03-11 2005-10-13 Dentsply De Trey Gmbh Composition de resine de scellement destinee a proteger des tissus durs

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1905098A1 (de) * 1969-02-01 1970-08-13 Bayer Ag Verfahren zur Herstellung von Polyamiden
DE2250134A1 (de) * 1972-10-13 1974-04-25 Cassella Farbwerke Mainkur Ag Verfahren zur herstellung von substituierten harnstoffen
US4374771A (en) * 1982-03-08 1983-02-22 American Cyanamid Company Blocked isocyanate
JPS61171732A (ja) * 1985-01-23 1986-08-02 Unitika Ltd 高重合度ポリアミドの製造法
WO2003061722A2 (fr) * 2002-01-23 2003-07-31 Scimed Life Systems, Inc. Dispositifs medicaux employant des polymeres a chaine etendue
WO2003070785A1 (fr) * 2002-02-21 2003-08-28 Dsm Ip Assets B.V. Procede de preparation de polymeres fonctionnalises et de produits intermediaires, compositions et parties faconnees
WO2004074342A1 (fr) * 2003-02-19 2004-09-02 Orteq B.V. Procede de preparation de nouveaux polyurethannes segmentes presentant des resistances elevees a la dechirure et a la traction et procede de production de greffes poreuses servant de support
WO2005094757A1 (fr) * 2004-03-11 2005-10-13 Dentsply De Trey Gmbh Composition de resine de scellement destinee a proteger des tissus durs

Non-Patent Citations (2)

* Cited by examiner, † Cited by third party
Title
DATABASE CAPLUS CHEMICAL ABSTRACTS SERVICE, COLUMBUS, OHIO, US; Y. IWAKURA: "Synthetic researches on synthetic fibers", XP002438219, Database accession no. 1950:26071 *
Y. IWAKURA: "Synthetic researches on synthetic fibers.", KOBUNSHI KAGAKU, vol. 2, 1945, pages 282 - 286 *

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