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EP2448988A1 - Compositions à base de diisocyanates issus de matières premières renouvelables - Google Patents

Compositions à base de diisocyanates issus de matières premières renouvelables

Info

Publication number
EP2448988A1
EP2448988A1 EP10715539A EP10715539A EP2448988A1 EP 2448988 A1 EP2448988 A1 EP 2448988A1 EP 10715539 A EP10715539 A EP 10715539A EP 10715539 A EP10715539 A EP 10715539A EP 2448988 A1 EP2448988 A1 EP 2448988A1
Authority
EP
European Patent Office
Prior art keywords
component
diisocyanate
composition according
nco
acid
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP10715539A
Other languages
German (de)
English (en)
Inventor
Jan Pfeffer
Martina Ortelt
Emmanouil Spyrou
Thomas Haas
Uwe Korek
Harald Schmidt
Uwe Dingerdissen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Evonik Operations GmbH
Original Assignee
Evonik Degussa 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 Evonik Degussa GmbH filed Critical Evonik Degussa GmbH
Publication of EP2448988A1 publication Critical patent/EP2448988A1/fr
Withdrawn legal-status Critical Current

Links

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
    • 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
    • C08G18/30—Low-molecular-weight 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/40—High-molecular-weight 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

Definitions

  • compositions based on diisocyanates from renewable raw materials are disclosed.
  • the invention relates to compositions based on 2,5-diisocyanato-1, 4: 3,6-dianhydro-2,5-dideoxy-D-mannitol (I), 2,5-diisocyanato-1, 4: 3,6 Dianhydro-2,5-dideoxy-D-glucitol (II) and / or 2,5-diisocyanato-1,4: 3,6-dianhydro-2,5-dideoxy-L-iditol (III), alone or in any mixtures.
  • Renewable raw materials refer to agricultural and forestry-produced products that are not used as food or feed. They are used materially, but also for the production of heat, electricity or fuels.
  • Polyurethanes from customary isocyanates known in polyurethane chemistry and 1: 4 - 3: 6 dianhydrohexitols are known from US 4,443,563 and DE-OS 31 11 093. Disadvantage is the restriction to Dianhydrohexitole, what the
  • polyurethanes of certain monoisocyanates based on 1: 4 - 3: 6 dianhydrohexitols are known (Thiem, J., et al., Macromol Rapid Comman., 19, 21-26, 1998).
  • the object of the invention was to find new compositions based on diisocyanates and polyisocyanates from renewable raw materials.
  • the invention relates to compositions essentially comprising a reaction product of
  • 2,5-diisocyanato-1, 4 3,6-dianhydro-2,5-dideoxy-D-mannitol (I), 2,5-diisocyanato
  • 05: 1 is preferably 0.5: 1 to 1: 1,
  • the diisocyanato-dianhydro-hexitols (I-III) which are reacted here belong to a group of chemical derivatives of so-called renewable raw materials, here in particular (poly) saccharides, for which purpose, for example.
  • renewable raw materials here in particular (poly) saccharides, for which purpose, for example.
  • the particular advantage of these compounds and their application products is that increasingly less fossil fuels such as oil, gas and coal are used in their manufacture, which reduces CO 2 emissions and thus the transition to CO 2 -neutral and fossil fuels Protecting raw materials
  • compositions of the invention certain properties, such. B.
  • oligoisocyanates or polyisocyanates which are prepared from said diisocyanates or mixtures thereof by linking with urethane, allophanate, urea, biuret, uretdione, amide, isocyanurate,
  • Carbodiimide, uretonimine, oxadiazinetrione or iminooxadiazinedione structures are particularly suitable. Particularly suitable are isocyanurates and uretdiones.
  • the component A) according to the invention can also be chain-extended.
  • the chain extender component can be polyester, as described below
  • polyamines can be used with two or more polyisocyanate-reactive amino groups.
  • Suitable polyamines are, for.
  • adipic dihydrazide ethylenediamine, diethylenetriamine, Thethylenentetramin, tetraethylenepentamine, pentaethylenehexamine, dipropylenetriamine, hexamethylenediamine, hydrazine, isophoronediamine, N- (2-aminoethyl) -2-aminoethanol, 1, 3- and 1, 4-phenylenediamine, 4.4 'Diphenylmethanediamine, amino functional
  • Component A) may also contain additional di- and polyisocyanates.
  • the di- and polyisocyanates used can be selected from any aromatic, aliphatic, cycloaliphatic and / or (cyclo) aliphatic di- and / or
  • aromatic di- or polyisocyanates are suitable as aromatic di- or polyisocyanates. Particularly suitable are 1, 3 and 1, 4-phenylene diisocyanate,
  • MDI Diphenylmethane diisocyanates
  • polymeric MDI oligomeric diphenylmethane diisocyanates
  • xylylene diisocyanate tetramethylxylylene diisocyanate
  • Suitable aliphatic di- or polyisocyanates advantageously have 3 to 16 carbon atoms, preferably 4 to 12 carbon atoms, in the linear or branched alkylene radical and suitable cycloaliphatic or (cyclo) aliphatic diisocyanates advantageously 4 to 18 carbon atoms, preferably 6 to 15 carbon atoms, in the cycloalkylene radical.
  • (cyclo) aliphatic diisocyanates The skilled worker understands at the same time cyclic and aliphatic bound NCO groups, as z. B. isophorone diisocyanate is the case. In contrast, is meant by cycloaliphatic diisocyanates those which have only directly attached to the cycloaliphatic ring NCO groups, for. B. Hi 2 MDI.
  • Examples are cyclohexane diisocyanate, methylcyclohexane diisocyanate,
  • Nonane triisocyanate such as 4-isocyanatomethyl-1, 8-octane diisocyanate (TIN), decane and triisocyanate, undecanediisocyanate and triisocyanate, dodecane diisocyanates and isocyanates.
  • TIN 4-isocyanatomethyl-1, 8-octane diisocyanate
  • decane and triisocyanate undecanediisocyanate and triisocyanate
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • Hi 2 MDI diisocyanatodicyclohexylmethane
  • MPDI 2-methylpentane diisocyanate
  • TMDI 2,2,4-thmethylhexamethylene diisocyanate / 2,4,4-thmethylhexamethylene diisocyanate
  • NBDI norbornane diisocyanate
  • mixtures of di- and polyisocyanates can be used.
  • the isocyanates of component A) may be partially or completely blocked.
  • blocking agents all blocking agents can be used.
  • phenols such as phenol, and p-chlorophenol
  • alcohols such as
  • Benzyl alcohol, oximes such as acetone oxime, methyl ethyl ketoxime, cyclopentanone oxime, cyclohexanone oxime, methyl isobutyl ketoxime, methyl tert-butyl ketoxime,
  • Malonic acid esters such as diisopropylamine, heterocyclic compounds having at least one heteroatom such as mercaptans, piperidines, piperazines, pyrazoles, imidazoles, triazoles and tetrazoles, ⁇ -hydroxybenzoic acid esters such as glycolic acid esters or hydroxamic acid esters such as Benzylmethacrylohydroxamat be used.
  • amines such as diisopropylamine
  • heterocyclic compounds having at least one heteroatom such as mercaptans, piperidines, piperazines, pyrazoles, imidazoles, triazoles and tetrazoles
  • ⁇ -hydroxybenzoic acid esters such as glycolic acid esters or hydroxamic acid esters such as Benzylmethacrylohydroxamat be used.
  • blocking agents are acetone oxime, methyl ethyl ketoxime, acetophenone oxime, diisopropylamine, 3,5-dimethylpyrazole, 1, 2,4-triazole,
  • Suitable functional groups are: OH, NH 2 , NH, SH, CH-acidic groups.
  • the compounds B) preferably contain 2 to 4 functional groups. Particularly preferred are alcohol groups and amino groups.
  • diamines and polyamines are in principle suitable: 1, 2-ethylenediamine,
  • Polypropylene oxides adducts of salts of 2-acrylamido-2-methylpropane-1-sulfonic acid and hexamethylenediamines, which may also carry one or more CrC 4 - alkyl radicals, called.
  • disecondary or primary / secondary diamines as described, for. B. in a known manner from the
  • diprimary diamines by reaction with a carbonyl compound, such as.
  • a carbonyl compound such as.
  • a ketone or aldehyde and subsequent hydrogenation or by Addition of diprimary diamines to acrylic acid esters or Maleinklahvate be used.
  • suitable amino alcohols are monoethanolamine, 3-amino-1-propanol, isopropanolamine, aminoethoxyethanol, N- (2-aminoethyl) ethanolamine,
  • CH-acidic compounds for example, derivatives of malonic acid esters, acetylacetone and / or acetoacetic ester are suitable.
  • Suitable compounds B) are in particular all diols and polyols usually used in PU chemistry with at least two OH groups.
  • diols and polyols z As diols and polyols z.
  • ethylene glycol 1, 2, 1, 3-propanediol, diethylene, dipropylene, triethylene, tetraethylene glycol, 1, 2, 1, 4-butanediol,
  • Neopentyl glycol trimethylolethane, trimethylolpropane, pentaerythritol, bisphenol A, B, C, F, norbornylene glycol, 1,4-benzyldimethanol, ethanol, 2,4-dimethyl-2-ethylhexane-1,3-diol, 1,4 and 2 , 3-butylene glycol, di-.beta.-hydroxyethylbutandiol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 8-octanediol, decanediol, dodecanediol, neopentyl glycol,
  • Ethylene glycol ethylene glycol, pentanediol-1, 5, hexanediol-1, 6, 3-methylpentanediol-1, 5, neopentyl glycol, 2,2,4 (2,4,4) -thimethylhexanediol, and
  • Hydroxypivalate They are used alone or in mixtures. 1, 4-butanediol is used only in mixtures.
  • Suitable compounds B) are also diols and polyols which contain further functional groups. These are the linear or slightly branched hydroxyl-containing polyesters, polycarbonates, known per se.
  • Polycaprolactones polyethers, polythioethers, polyesteramides, polyacrylates,
  • Polyvinyl alcohols, polyurethanes or polyacetals They preferably have a number average molecular weight of 134 to 20,000 g / mol, more preferably 134-4000 g / mol.
  • the polymers containing hydroxyl groups preferably use polyesters, polyethers, polyacrylates, polyurethanes, polyvinyl alcohols and / or polycarbonates having an OH number of 5 to 500 (in mg KOH / gram).
  • Suitable diols and polyols for the preparation of the preferred polyester polyols are, in addition to the abovementioned diols and polyols, 2-methylpropanediol, 2,2-dimethylpropanediol, diethylene glycol, dodecanediol-1, 12, 1, 4-cyclohexanedimethanol and 1, 2 and 1, 4 -Cyclohexandiol.
  • Suitable dicarboxylic acids or derivatives for the preparation of the polyester polyols may be aliphatic, cycloaliphatic, aromatic and / or heteroaromatic nature and optionally, for. B. by halogen atoms, substituted and / or unsaturated.
  • Preferred dicarboxylic acids or derivatives include succinic, adipic, corkic, azelaic and sebacic acids, 2,2,4 (2,4,4) -thmethyl-adipic acid, phthalic acid, phthalic anhydride, isophthalic acid, terephthalic acid,
  • Suitable polyester polyols are also those which in a known manner by ring opening from lactones, such as caprolactone, and simple diols as
  • Polyphenols of the above type Polyester of boric acid; Polysiloxanes, such as.
  • the products obtainable by hydrolysis of dialkyldichlorosilanes with water and subsequent treatment with polyalcohols which are obtainable by addition of polysiloxane dihydrides to olefins, such as allyl alcohol or acrylic acid, are suitable as Starting materials for the preparation of the compounds B).
  • the polyesters can be obtained in a conventional manner by condensation in an inert gas atmosphere at temperatures of 100 to 260 0 C, preferably 130 to 220 0 C, in the melt or in azeotropic procedure, as it is z.
  • in methods of organic chemistry Houben-Weyl; Volume 14/2, pages 1 to 5, 21 to 23, 40 to 44, Georg Thieme Verlag, Stuttgart, 1963, or CR
  • OH-containing (meth) acrylates are also preferably used.
  • the diols and dicarboxylic acids or derivatives thereof used for the preparation of the polyesterpolyols can be used in any desired mixtures.
  • Suitable compounds B) are also the reaction products of polycarboxylic acids and glycidic compounds, as described, for. B. in DE-OS 24 10 513 are described.
  • glycidyl compounds which can be used are esters of 2,3-epoxy-1-propanol with monobasic acids having 4 to 18 carbon atoms, such as glycidyl palmitate, glycidyl laurate and glycidyl stearate, alkylene oxides of 4 to 18 carbon atoms, such as butylene oxide, and Glycidyl ethers, such as octyl glycidyl ether.
  • Compounds B) are also those which carry at least one further functional group in addition to an epoxide group, such as.
  • an epoxide group such as.
  • carboxyl, hydroxyl, mercapto or amino groups which is capable of reacting with an isocyanate group.
  • Particularly preferred are 2,3-epoxy-1-propanol and epoxidized soybean oil.
  • reaction of components A) and B) can be carried out in suitable units, stirred tanks, static mixers, tubular reactors, kneaders, extruders or other reaction spaces with or without mixing function.
  • the reaction is carried out at temperatures between room temperature and 220 0 C, preferably between 40 0 C and 120 0 C and takes depending on the temperature and
  • Reaction components A) and B) between a few seconds and several weeks. A reaction time between 30 minutes and 24 hours is preferred.
  • the ratio between the NCO component A) and the NCO-reactive functional group-containing component B), calculated as NCO / NCO-reactive 0.3: 1 to 1, 05: 1, preferably 0.5: 1 to 1: 1.
  • the final product has no significant free NCO groups
  • the catalysts customary in PU chemistry can be used. They are used in a concentration of 0.001 to 2 wt .-%, preferably from 0.01 to 0.5 wt .-%, based on the reaction components used. Catalysts are for example tert. Amines such as thethylamine, pyridine or N, N-dimethylaminocyclohexane or metal salts such as iron (III) chloride, molybdenum glycolate and zinc chloride. As special suitable tin-Il and -IV compounds proved. Dibutyltin dilaurate (DBTL) and tin octoate may be mentioned here in particular.
  • DBTL dibutyltin dilaurate
  • tin octoate may be mentioned here in particular.
  • compositions of the invention may be solid, viscous, liquid and also in powder form.
  • compositions may also contain auxiliaries and additives,
  • inhibitors selected from inhibitors, organic solvents, optionally
  • unsaturated groupings surface-active substances, oxygen and / or radical scavengers, catalysts, light stabilizers, color brighteners,
  • Photoinitiators photosensitizers, thixotropic agents,
  • Anti-skinning agents defoamers, dyes, pigments, fillers and matting agents.
  • the amount varies greatly from the field of application and type of auxiliary and additive.
  • Suitable organic solvents are all liquid substances which do not react with other ingredients, eg. Acetone, ethyl acetate, butyl acetate, xylene,
  • the usual additives such as leveling agents, for. As polysilicones or acrylates, light stabilizers, for. B. hindered amines, or other auxiliaries, such as. As described in EP 0 669 353, in a total amount of 0.05 to 5 wt .-% are added. Fillers and pigments such. Titanium dioxide may be added in an amount of up to 50% by weight of the total composition.

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

Abstract

L'invention concerne des compositions à base de 2,5-diisocyanato-1,4:3,6-dianhydro-2,5-didésoxy-D-manitol (I), 2,5-diisocyanato-1,4:3,6-dianhydro-2,5- didésoxy-D-glucitol (II) et/ou 2,5-diisocyanato-1,4:3,6-dianhydro-2,5-didésoxy-L-iditol (III), seuls ou dans des mélanges quelconques.
EP10715539A 2009-07-01 2010-04-23 Compositions à base de diisocyanates issus de matières premières renouvelables Withdrawn EP2448988A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009027392A DE102009027392A1 (de) 2009-07-01 2009-07-01 Zusammensetzung auf der Basis von Diisocyanaten aus nachwachsenden Rohstoffen
PCT/EP2010/055414 WO2011000585A1 (fr) 2009-07-01 2010-04-23 Compositions à base de diisocyanates issus de matières premières renouvelables

Publications (1)

Publication Number Publication Date
EP2448988A1 true EP2448988A1 (fr) 2012-05-09

Family

ID=42236497

Family Applications (1)

Application Number Title Priority Date Filing Date
EP10715539A Withdrawn EP2448988A1 (fr) 2009-07-01 2010-04-23 Compositions à base de diisocyanates issus de matières premières renouvelables

Country Status (7)

Country Link
US (1) US20120077932A1 (fr)
EP (1) EP2448988A1 (fr)
JP (1) JP2012531507A (fr)
CN (1) CN102471451A (fr)
AU (1) AU2010268317A1 (fr)
DE (1) DE102009027392A1 (fr)
WO (1) WO2011000585A1 (fr)

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DE102007060705A1 (de) 2007-12-17 2009-06-18 Evonik Degussa Gmbh ω-Aminocarbonsäuren oder ihre Lactame, herstellende, rekombinante Zellen
DE102008002715A1 (de) 2008-06-27 2009-12-31 Evonik Röhm Gmbh 2-Hydroxyisobuttersäure produzierende rekombinante Zelle
DE102010015807A1 (de) 2010-04-20 2011-10-20 Evonik Degussa Gmbh Biokatalytisches Oxidationsverfahren mit alkL-Genprodukt
DE102010041247A1 (de) 2010-09-23 2012-03-29 Evonik Degussa Gmbh Verfahren zur Herstellung von lagerstabilen Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung in Lösung
DE102010043470A1 (de) 2010-11-05 2012-05-10 Evonik Degussa Gmbh Zusammensetzung aus Polyamiden mit niedriger Konzentration an Carbonsäureamidgruppen und elektrisch leitfähigem Kohlenstoff
DE102011006163A1 (de) 2011-03-25 2012-09-27 Evonik Degussa Gmbh Lagerstabile Polyurethan-Prepregs und daraus hergestellte Formkörper aus Polyurethanzusammensetzung mit flüssigen Harzkomponenten
EP2631298A1 (fr) 2012-02-22 2013-08-28 Evonik Industries AG Procédé biotechnologique et procédé de production de butanol et d'acide butyrique
EP2639308A1 (fr) 2012-03-12 2013-09-18 Evonik Industries AG Omega-oxydation et -amination enzymatique d'acides gras
US9695935B2 (en) 2012-08-23 2017-07-04 Eagle Industry Co., Ltd. Sealing device
DE102012219324A1 (de) 2012-10-23 2014-04-24 Evonik Industries Ag Zusammensetzungen umfassend alkoxysilanhaltige Isocyanateund saure Stabilisatoren
EP2945994B1 (fr) 2013-01-18 2018-07-11 Basf Se Compositions de revêtement à base de dispersion acrylique
KR101602467B1 (ko) * 2015-08-24 2016-03-15 로움하이텍 주식회사 신규한 폴리우레탄 화합물 및 이를 포함하는 반사방지막 조성물
EP3263619A1 (fr) * 2016-06-27 2018-01-03 Evonik Degussa GmbH Moyens de revêtement fonctionnalisés par un alkoxysilane et un allophanate
EP3263616B8 (fr) 2016-06-27 2020-01-15 Evonik Operations GmbH Moyens de revêtement fonctionnalisés par un alkoxysilane et contenant un allophanate
EP3401344B1 (fr) 2017-05-09 2020-04-08 Evonik Operations GmbH Procédé de fabrication de trimères et/ou d'oligomères de diisocyanates
US20230151248A1 (en) * 2021-11-16 2023-05-18 H.B. Fuller Company Sustainable reactive hot melt adhesive compositions

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Also Published As

Publication number Publication date
JP2012531507A (ja) 2012-12-10
WO2011000585A1 (fr) 2011-01-06
CN102471451A (zh) 2012-05-23
US20120077932A1 (en) 2012-03-29
AU2010268317A1 (en) 2011-12-15
DE102009027392A1 (de) 2011-01-05

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