WO2008142101A1 - Procédé de fabrication d'uréthanes à terminaison carbonate multiple - Google Patents

Procédé de fabrication d'uréthanes à terminaison carbonate multiple Download PDF

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Publication number
WO2008142101A1
WO2008142101A1 PCT/EP2008/056244 EP2008056244W WO2008142101A1 WO 2008142101 A1 WO2008142101 A1 WO 2008142101A1 EP 2008056244 W EP2008056244 W EP 2008056244W WO 2008142101 A1 WO2008142101 A1 WO 2008142101A1
Authority
WO
WIPO (PCT)
Prior art keywords
general formula
alkylene
compound
iii
compounds
Prior art date
Application number
PCT/EP2008/056244
Other languages
German (de)
English (en)
Inventor
Andreas Job
Lars Rodefeld
Original Assignee
Saltigo Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Saltigo Gmbh filed Critical Saltigo Gmbh
Publication of WO2008142101A1 publication Critical patent/WO2008142101A1/fr

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/771—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur oxygen
    • 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
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/80—Masked polyisocyanates
    • C08G18/8061—Masked polyisocyanates masked with compounds having only one group containing active hydrogen
    • C08G18/8064—Masked polyisocyanates masked with compounds having only one group containing active hydrogen with monohydroxy compounds

Definitions

  • the present invention relates to a process for preparing polycarbonate-terminated urethanes.
  • Material surfaces can be made biocompatible, for example, by coating with heparin.
  • Other applications include antisoiling and bacteriostatic finishing and improving the adhesion of adhesives and paints.
  • the targeted modification of biomolecules is desirable in many cases.
  • it is known that the biological half-life of various drugs can be improved by adding polyoxyalkylene radicals.
  • R ' is Ci-Ci 2 alkylene and R "can represent a variety of organic radicals
  • These reactive cychschen carbonates can be reacted with nucleophiles, such as hydroxy or primary or secondary amino groups of biomolecules, polymers or on substrate surfaces, where it is used to open the cyclic carbonation comes with simultaneous covalent attachment to the biomolecule, the polymer or other substrate surfaces.
  • US-A-5,115,045 relates to isocyanate-reactive compositions useful in the preparation of
  • Polyurethanes are used. These isocyanate-reactive compositions are based on the reaction product of (a) a di- or polychloroformate ester of the type Q- [X-CO Y] n , where X can be oxygen and Y is chlorine, n is at least 2 and Q is an organic radical, with (b) a multifunctional compound which, in addition to the functional groups which react with the di- or polychloroformate ester (a), must contain at least one
  • Enammogroup must contain. No di- or polychloroformate esters (a) are described which have cyclic carbonate groups. The di- or polychloroformate esters are prepared by reacting polyols with acylating agents such as phosgene. From the imino and / or enamino groups contained in the multi-functional compound (b), an isocyanate-reactive amino group can later be obtained by hydrolysis.
  • this invention Since there is a high demand for reactive cyclic carbonates for surface treatment, this invention has the object to provide an improved manufacturing process.
  • the invention relates to a process for the preparation of compounds of general formula (I), embedded image in which
  • R 1 is dC-alkylene, k is an integer greater than 1 and
  • R is a k-valent aliphatic, cycloaliphatic, aromatic or araliphatic hydrocarbon radical which optionally contains one or more heteroatoms, by reaction of a compound of the general formula (II)
  • R 1 has the meaning given for general formula (I), with a compound of general formula (III),
  • An advantage of the inventive method is the avoidance of phenol as a minor component. It is particularly advantageous that this reaction is an addition reaction in which, in principle, no further secondary components are formed. It is thus a process which yields a complete atomic-economical yield.
  • the isocyanates of the general formula (III) can be prepared by reacting the corresponding amines of the general formula (IV) with phosgene,
  • R 1 denotes a C 1 -C 6 -alkylene radical, particularly preferably a methylene, ethylene,
  • Propylene, n-butylene or n-hexamethylene radical represents.
  • R 2 is a k-valent, especially dl- or trivalent, aliphatic, cycloahphatic, aromatic or araliphatic hydrocarbon radical which optionally contains one or more heteroatoms.
  • R 2 is a di- or trivalent, ahphatician, cycloaliphaüschen, aromatic or araliphatic hydrocarbon radical containing only one or more oxygen atoms as heteroatoms.
  • R 2 is a - [(C 2 -C 6 -alkylene-O-) ⁇ - (C 2 -C 6 -alkylene)] - group in which the two
  • Suitable amines of the general formula (IV) which can be used for the preparation of the compounds of the general formula (III) are, for example, the following:
  • Polyether diamides ethylene diamine, propylene diamine, butylene diamine, hexamethylene diamine, MDA, TDA, diarmnobenzene, diammocyclohexane, diammomethylcyclohexane, TCD-Diamm, 1,4-bis- (3-ammopropyloxy) butane, T ⁇ s- (2-ammoethyl) amm, l, 4- Bis (3-ammopropyl) prperazm, bis (3-ammopropyl) amm and triethylene.
  • Suitable polyetherdiams of the general formula (IV) which can be used to prepare the compounds of the general formula (III) are commercial products of the Huntsman Corporation such as Jeffamm D-230, Jeffamm D-400, Jeffamm D-2000, Jeffamm D-4000, Jeffamm ED-600, Jeffamm ED-2003 and Jeffamm EDR-148.
  • 1 to 2 equivalents of the compound of the general formula (II) are used relative to 1 equivalent of the compound of the general formula (III).
  • the erfmdungswele process is usually carried out at a temperature in the range of 0 0 C to 22O 0 C.
  • the erfmdungshiele process at a temperature in the range of 10 0 C to 200 0 C and particularly preferably in the range of 20 0 C to 15O 0 C performed
  • the inventive method can be carried out so that the compound of general formula (III), optionally dissolved in an inert solvent, and then the compound of general formula (II), optionally also dissolved in the same or m a different inert solvent to which isocyanate is added.
  • the compound of the general formula ( ⁇ ) is initially charged and then the compound of the general formula (III) is added, where both substances may optionally be diluted with the same or different inert solvent.
  • the method according to the invention can also be operated continuously. In doing so, the
  • Suitable solvents are, for example, toluene, xylenes, chlorobenzene, 1,2-dichlorobenzene, tetrahydrofuran, diethyl ether, dioxane, methyltetrahydrofuran, cyclopentylmethyl ether, dibutyl ether, 1,2-dichloroethane, dichloromethane, chloroform, dimethoxyethane, acetonitrile, cyclohexane, methylcyclohexane, cyclopentane, heptane, Hexane, diethylene glycol dimethyl ether,
  • the isolation of the compounds of the general formula (I) can be carried out by distillation, crystallization, chromatography or freeze-drying.
  • the compounds of the general formula (I) obtained by the process according to the invention can be reacted with functional groups, such as hydroxy groups or primary or secondary amino groups, which are contained in biomolecules, polymers or substrate surfaces.
  • the cyclic carbonate ring is opened with covalent bonding to the Biomolecule, the polymer or the substrate surface. In this way it is possible to introduce the above-defined plurality of radicals R 2 and R 3 into biomolecules or polymers or to bind them to substrate surfaces.
  • biomolecule is intended to encompass all molecules which can be isolated from biological systems and / or which can interact with biological systems or parts thereof, in particular peptides, proteins, proteoglycans, enzymes, markers, antibodies, receptor molecules, Antigens and drugs Specific examples are heparin, tissue plasminogen activator, streptokinase and prostaglandins.
  • polymers for example, polyamines or polyols can be used.
  • polyamines are examples of polyamines.
  • surfaces that can be treated by this method for example, the surfaces of materials are suitable which have ammo and / or hydroxyl groups, or surfaces which have been treated by methods known per se with Ammosilanen
  • the compounds of the general formula (I) obtained by the process according to the invention can be reacted with diamines to form so-called block copolymers.
  • Suitable diameters are, for example, polyether diamines or diammopolysiloxanes. The latter implementation is disclosed in a German patent application filed on the same day by the Momentive Performance Mate ⁇ als.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Emergency Medicine (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

L'invention concerne un procédé amélioré de fabrication d'uréthanes à terminaison carbonate au moyen de di-isocyanates ou de poly-isocyanates. Ledit procédé se caractérise par des rendements élevés et par l'absence de production de phénols en tant que composants secondaires.
PCT/EP2008/056244 2007-05-21 2008-05-21 Procédé de fabrication d'uréthanes à terminaison carbonate multiple WO2008142101A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102007023868.3 2007-05-21
DE200710023868 DE102007023868A1 (de) 2007-05-21 2007-05-21 Verfahren zur Herstellung von mehrfach Corbonat-terminierter Urethanen

Publications (1)

Publication Number Publication Date
WO2008142101A1 true WO2008142101A1 (fr) 2008-11-27

Family

ID=39830243

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2008/056244 WO2008142101A1 (fr) 2007-05-21 2008-05-21 Procédé de fabrication d'uréthanes à terminaison carbonate multiple

Country Status (2)

Country Link
DE (1) DE102007023868A1 (fr)
WO (1) WO2008142101A1 (fr)

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3094538A (en) * 1958-05-21 1963-06-18 Dow Chemical Co Carbonatopropyl dicarbamates
EP0346669A1 (fr) * 1988-06-11 1989-12-20 Bayer Ag Procédé pour la préparation de combinaisons de liants durcissables, les combinaisons ainsi obtenues et leur utilisation
WO2002079148A2 (fr) * 2001-03-30 2002-10-10 Huntsman Petrochemical Corporation Carbonates multifonctionnels et derives

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4002598A (en) 1975-03-06 1977-01-11 Texaco Development Corporation Polyether urea epoxy curing agent
DE3804820A1 (de) 1988-02-12 1989-08-17 Dainippon Ink & Chemicals Cyclocarbonathaltige ester und verfahren zu ihrer herstellung
GB8905768D0 (en) 1989-03-13 1989-04-26 Ici Plc Compositions of matter
EP1541568A1 (fr) 2003-12-09 2005-06-15 Deutsches Wollforschungsinstitut an der Rheinisch-Westfälischen Technischen Hochschule Aachen e.V. Carbonates et urées cycliques et réactifs pour la modification de biomolecules, polymères et surfaces

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3094538A (en) * 1958-05-21 1963-06-18 Dow Chemical Co Carbonatopropyl dicarbamates
EP0346669A1 (fr) * 1988-06-11 1989-12-20 Bayer Ag Procédé pour la préparation de combinaisons de liants durcissables, les combinaisons ainsi obtenues et leur utilisation
WO2002079148A2 (fr) * 2001-03-30 2002-10-10 Huntsman Petrochemical Corporation Carbonates multifonctionnels et derives

Also Published As

Publication number Publication date
DE102007023868A1 (de) 2008-11-27

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