EP0000016B1 - Verfahren zur Herstellung von Allophanatgruppen aufweisenden Polyisocyanaten und ihre Verwendung als Aufbaukomponente - Google Patents

Verfahren zur Herstellung von Allophanatgruppen aufweisenden Polyisocyanaten und ihre Verwendung als Aufbaukomponente Download PDF

Info

Publication number
EP0000016B1
EP0000016B1 EP78100028A EP78100028A EP0000016B1 EP 0000016 B1 EP0000016 B1 EP 0000016B1 EP 78100028 A EP78100028 A EP 78100028A EP 78100028 A EP78100028 A EP 78100028A EP 0000016 B1 EP0000016 B1 EP 0000016B1
Authority
EP
European Patent Office
Prior art keywords
groups
polyisocyanates
mol
isocyanate
reaction
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.)
Expired
Application number
EP78100028A
Other languages
German (de)
English (en)
French (fr)
Other versions
EP0000016A1 (de
Inventor
Manfred Dr. Bock
Josef Dr. Pedain
Wilhelm Dr. Slawyk
Klaus Dr. König
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.)
Bayer AG
Original Assignee
Bayer AG
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 Bayer AG filed Critical Bayer AG
Publication of EP0000016A1 publication Critical patent/EP0000016A1/de
Application granted granted Critical
Publication of EP0000016B1 publication Critical patent/EP0000016B1/de
Expired 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
    • C08G18/80—Masked polyisocyanates
    • C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
    • C08G18/8054—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38
    • C08G18/8058—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen with compounds of C08G18/38 with compounds of C08G18/3819
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C273/00—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups
    • C07C273/18—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas
    • C07C273/1809—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety
    • C07C273/1836—Preparation of urea or its derivatives, i.e. compounds containing any of the groups, the nitrogen atoms not being part of nitro or nitroso groups of substituted ureas with formation of the N-C(O)-N moiety from derivatives of carbamic acid
    • 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
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • 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
    • C08G18/78—Nitrogen
    • C08G18/7806—Nitrogen containing -N-C=0 groups
    • C08G18/7818—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups
    • C08G18/7837—Nitrogen containing -N-C=0 groups containing ureum or ureum derivative groups containing allophanate groups

Definitions

  • the present invention relates to a new process for the production of new allophanate organic polyisocyanates having at least three isocyanate groups and their use as a structural component in the production of polyurethane plastics.
  • Organic polyisocyanates containing allophanate groups and having aliphatic bound isocyanate groups have become known, for example, from GB-PS 994 890. According to this patent, polyisocyanates containing urethane groups from simple mono- or polyhydric alcohols and organic polyisocyanates, in particular diisocyanates, are reacted by heating to elevated temperatures for several hours or, in the presence of catalysts, with further amounts of organic polyisocyanates, preferably diisocyanates, to form the allophanate groups-containing polyisocyanates.
  • a disadvantage of this process, in addition to the use of catalysts is in particular the long heating time during the allophanatization reaction, which generally leads to discolored reaction products.
  • Hydroxyalkyl radicals mean and the radicals R 3 and R s together with the two carbon atoms of the basic structure can also form a cycloaliphatic ring.
  • the present invention also relates to the use of the polyisocyanates produced by this process as a structural component in the production of polyurethane plastics by the isocyanate polyaddition process.
  • the compounds containing hydroxyl groups which are essential to the invention and are to be used in the process according to the invention are preferably those of the formula mentioned in which.
  • R 1 and R 2 represent the same or different radicals and are hydrogen, C 2 ⁇ C 18 -, in particular C 2 ⁇ C 6 -hydroxyalkyl groups, C 1 ⁇ C 18 - in particular C 1 ⁇ C 4 alkyl groups or C 4 ⁇ C 15 C 6 -C 10 cycloalkyl groups, in which at least one of the radicals R 1 or R 2 represents hydrogen or a hydroxyalkyl group,
  • R 3 , R 4 , R 5 and R e represent the same or different radicals and are hydrogen, C 1 ⁇ C 13 - in particular C 1 ⁇ C 12 -alkyl groups or C 1 ⁇ C 18 - in particular C 1 ⁇ C 2 -hydroxyalkyl groups , wherein the radicals R 3 and R 5 together with the two carbon atoms of the backbone can also represent a cycloaliphatic ring with 5-6 carbon atoms, and wherein at least two of the radicals R 3 , R 4 , R 5 and R e represent hydrogen.
  • the compounds of the general formula mentioned which contain essential hydroxyl groups can easily be obtained by reacting compounds of the formula having amino groups with cyclic carbonates of the formula be preserved.
  • R t to Rg have the meaning given above.
  • suitable compounds containing amino groups are ammonia, methylamine, ethylamine, propylamine, isopropylamine, butylamine, sec-butylamine, isobutylamine, tert-butylamine, pentylamine, tert-pentylamine, hexylamine, 2-ethylhexylamine, dodecylamine, tetradecylamine, hexadecylamine, hexadecylamine, hexadecylamine, hexadecylamine, 2-propenylamine, cyclohexylamine, 2 (or 3, or 4) - methylcyclohexylamine, aminomethylcyclohexylamine, 3,3,5 - trimethylcyclohexylamine, 2 - norbornylmethylamine, 2 - aminoethanol, 3 - amino-1-propanol, 1-amino-2-propanol, 4 -
  • the compounds containing hydroxyl groups essential to the invention are generally prepared at 20 to 100 ° C., preferably 30 to 50 ° C., by reacting equimolar amounts of the compounds containing amino groups mentioned by way of example with the cyclic carbonates mentioned by way of example.
  • Any organic polyisocyanates are suitable for the process according to the invention.
  • Examples include ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 2,2,4 - (2,4,4) - trimethylhexymethylene diisocyanate - 1,6, 1,12 - dodecane diisocyanate, lysine diisocyanate - C 1 ⁇ C 8 - alkyl ester, cyclobutane 1,3-diisocyanate, cyclohexane, 1,3- and -1,4-diisocyanate and any mixtures of these isomers, 2,4- and 2,6-hexahydrotoluenediisocyanate and any mixtures of these isomers, 3,3'-dimethyl-4 , 4 '- diisocyanatodicyclohexylmethane, 4,4' - diiso
  • Hexamethylene diisocyanate and 1-isocyanato-3,3,5-tri are preferred methyl-5-isocyanatomethyl-cyclohexane (isophorone diisocyanate) was used.
  • the process according to the invention is carried out in the temperature range from 90-200 ° C., preferably 100-180 ° C.
  • the reactants are used in proportions which correspond to an NCO / OH equivalent ratio of at least 4: 1, preferably 6: 1 to 25: 1.
  • the process according to the invention can also be carried out in two stages in the same way, the starting components being stirred together at room temperature and then being heated together to the above-mentioned temperature range of 100-180 ° C.
  • a solvent which is inert to isocyanates e.g. Ethyl acetate, butyl acetate, toluene or xylene is possible.
  • the process according to the invention is preferably carried out without solvents.
  • the process products are viscous, colorless to yellow colored polyisocyanates, which are liquid at room temperature or are present as solid hard resins. They are completely odorless and clearly soluble in solvents which are inert to NCO groups, such as hydrocarbons, chlorinated hydrocarbons, esters and ketones.
  • urethane groups initially form from the hydroxyl groups of the compound having essential hydroxyl groups and part of the isocyanate groups of the diisocyanate.
  • These polyisocyanates thus containing intermediate urethane groups already form in the temperature range between 50 and 100 ° C. and can be isolated with appropriate temperature control, since at these temperatures essentially no allophanatization occurs.
  • At a higher temperature, above 100 ° C further diisocyanate is added to the urethane groups to form allophanates.
  • urethanization of the OH function and allophanatization proceed non-selectively and side by side.
  • polyisocyanate containing urethane groups in the temperature range between 50 and 100 ° C using an NCO / OH equivalent ratio of 1: 1, which polyisocyanate has either only aliphatic or exclusively cycloaliphatic isocyanate groups, followed by the allophanatization reaction in the temperature range from 100-180 ° C, in particular 110-150 ° C using excess amounts of a cycloaliphatic or aliphatic diisocyanate.
  • the excess diisocyanate which may still be present can be separated off by distillation, for example in thin-film evaporators, after the reaction according to the invention.
  • the process products according to the invention reproduce valuable starting materials for the production of polyurethane plastics the isocyanate polyaddition process, in particular for the production of one- or two-component polyurethane lacquers.
  • the process products according to the invention are also particularly suitable for producing polyurethane stoving lacquers.
  • Preferred reactants for the process products according to the invention are the polyhydroxy polyesters, polyhydroxy polyacrylates known per se in polyurethane lacquer technology and optionally low molecular weight, polyhydric alcohols. Suitable reactants of this type are described, for example, in DT-AS 2 304 893.
  • the proportions in which the optionally blocked polyisocyanates according to the invention and the reactants mentioned are reacted in the production of polyurethane lacquers are generally chosen so that 0.8-3, preferably 0.9-1, to an (optionally blocked) isocyanate group 1, hydroxyl, amino, mercapto and / or carboxyl groups are eliminated.
  • the catalysts customary in isocyanate chemistry, such as, for example, tert.
  • Amines such as triethylamine, pyridine, methylpyridine, benzyldimethylamine, N, N-dimethylaminocyclohexane, N-methylpiperidine, pentamethyldiethylenetriamine, N, N '- endoethylene piperazine, N, N' - dimethylpiperazine etc.
  • metal salts such as iron (III) chloride , zinc chloride, zinc - 2 - äthylcaproat, tin (II) - 2 - äthylcaproat, dibutyltin (IV) - dilaurate, molybdenum, etc .. d ssenlykolat
  • NCO groups are accounted for by one OH group.
  • paint binders with free NCO groups are created, which harden in moist air to form hard, shiny and high-quality coatings.
  • the catalysts mentioned can also be used in one-component paints.
  • the NCO groups are blocked in whole or in part in a known manner.
  • the polyisocyanate is treated with a suitable blocking agent, preferably at elevated temperature (e.g. 40 to 140 ° C), optionally in the presence of a suitable catalyst, e.g. tert.
  • a suitable blocking agent preferably at elevated temperature (e.g. 40 to 140 ° C)
  • a suitable catalyst e.g. tert.
  • Amines, metal salts such as zinc - 2 - ethyl caproate, tin (II) - 2 - ethyl caproate, dibutyl tin (IV) - dilaurate or alkali metal phenolate.
  • the paints and coatings can be in solvent-free liquid form or in solution or from the melt, or in solid form by the customary methods, e.g. Brushing, rolling, pouring, spraying, the vortex sintering process or the electrostatic powder spraying process are applied to the object to be coated.
  • the lacquers containing the polyisocyanates according to the invention give films which adhere surprisingly well to metallic substrates, are particularly lightfast, stable to heat colors and very resistant to rubbing and, if they are used in air-drying lacquers, dry particularly quickly, even at temperatures around 0.degree. In addition, they are characterized by great hardness, elasticity, excellent chemical resistance, high gloss, excellent weather resistance and good pigmentability.
  • homologue mixtures are used as reactants for the diisocyanates when carrying out the process according to the invention, which mixtures are obtained as such during their preparation.
  • the homolog mixture used in Example 2 consists of N - (2-hydroxyethyl) 2-hydroxy-1-methylethyl carbamate and N - (2-hydroxyethyl) 2-hydroxy-2-methylethyl carbamate in the reaction of 2-aminoethanol and 4 - methyl - 1,3 - dioxolan - 2 - one.
  • the methyl substituent can be in either the 1- or the 2-position.
  • the stability of the polyisocyanates shown is checked by annealing at 50 ° C. for several weeks and then analyzing the samples for their content of monomeric isocyanate by gas chromatography.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Paints Or Removers (AREA)
EP78100028A 1977-06-04 1978-06-01 Verfahren zur Herstellung von Allophanatgruppen aufweisenden Polyisocyanaten und ihre Verwendung als Aufbaukomponente Expired EP0000016B1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19772725318 DE2725318A1 (de) 1977-06-04 1977-06-04 Verfahren zur herstellung von allophanatgruppen aufweisenden polyisocyanaten
DE2725318 1977-06-04

Publications (2)

Publication Number Publication Date
EP0000016A1 EP0000016A1 (de) 1978-12-20
EP0000016B1 true EP0000016B1 (de) 1980-07-23

Family

ID=6010745

Family Applications (1)

Application Number Title Priority Date Filing Date
EP78100028A Expired EP0000016B1 (de) 1977-06-04 1978-06-01 Verfahren zur Herstellung von Allophanatgruppen aufweisenden Polyisocyanaten und ihre Verwendung als Aufbaukomponente

Country Status (6)

Country Link
US (1) US4177342A (enrdf_load_stackoverflow)
EP (1) EP0000016B1 (enrdf_load_stackoverflow)
JP (1) JPS543013A (enrdf_load_stackoverflow)
DE (2) DE2725318A1 (enrdf_load_stackoverflow)
ES (1) ES470460A1 (enrdf_load_stackoverflow)
IT (1) IT7849672A0 (enrdf_load_stackoverflow)

Families Citing this family (62)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS588946B2 (ja) * 1979-04-05 1983-02-18 株式会社 高橋プレス工場 前輪フオ−クの製造方法
DE3039824A1 (de) * 1980-10-22 1982-05-27 Bayer Ag, 5090 Leverkusen Neue lackpolyisocyanate, ein verfahren zu ihrer herstellung, sowie ihre verwendung als isocyanatkomponente in hitzehaertbaren zweikomponenten-polyurethanlacken
US4517222A (en) * 1983-03-10 1985-05-14 Ashland Oil, Inc. Vaporous amine catalyst spray method of applying a film to a substrate
JPS60118085U (ja) * 1984-01-20 1985-08-09 日立電線株式会社 管材の継手用スリ−ブ
JPS6196280A (ja) * 1984-10-15 1986-05-14 日立電線株式会社 金属スリ−ブによる金属管材の接続方法
JPS6170679U (enrdf_load_stackoverflow) * 1984-10-16 1986-05-14
EP0257848A3 (en) * 1986-08-14 1989-01-11 King Industries, Inc. Certain carbamates, processes for preparing same and use thereof
US4738991A (en) * 1987-01-23 1988-04-19 Basf Corporation Storage stable polyisocyanates characterized by allophanate linkages
US4810820A (en) * 1987-08-12 1989-03-07 Mobay Corporation Process for the production of polyisocyanates containing allophanate groups
JP2839096B2 (ja) * 1988-08-26 1998-12-16 臼井国際産業株式会社 管端部と相手部材との鑞付け方法
US5212015A (en) * 1989-06-14 1993-05-18 Minnesota Mining And Manufacturing Company Coated substrates comprising polymers derived from monocarbamate diols
US5163060A (en) * 1989-06-14 1992-11-10 Minnesota Mining And Manufacturing Company Second harmonic generator comprising an NLO-active polymer derived from monocarbamate diols
US5093456A (en) * 1989-06-14 1992-03-03 Minnesota Mining And Manufacturing Company Monocarbamate diols, polymers derived from them and nlo-active materials therefrom
AT394729B (de) * 1990-09-17 1992-06-10 Vianova Kunstharz Ag Verfahren zur herstellung von vernetzungskomponenten fuer kathodisch abscheidbarelackbindemittel
ES2087386T3 (es) * 1991-10-02 1996-07-16 Bayer Ag Poliisocianatos que contienen grupos alofanato e isocianurato, un procedimiento para su produccion y su empleo en composiciones de revestimiento de dos componentes.
JPH0621407U (ja) * 1992-05-30 1994-03-22 季子 上見 かかと部材交換靴
JPH0613510U (ja) * 1992-07-30 1994-02-22 由希子 安井 靴底構造
US5726274A (en) * 1994-12-21 1998-03-10 Basf Corporation Polyurethane polymer or oligomer having carbamate groups, method for its preparation, and coating composition
DE4416321A1 (de) 1994-05-09 1995-11-16 Bayer Ag Verfahren zur Herstellung von Allophanatgruppen aufweisenden lichtechten Polyisocyanaten
GB2291564B (en) * 1994-07-13 1999-02-10 Nec Corp Mobile communication for a mobile station near the boundary of or outside a service area of a base station
US5489704A (en) 1994-08-29 1996-02-06 Bayer Corporation Polyisocyanate/polyamine mixtures and their use for the production of polyurea coatings
US5541281A (en) 1994-12-20 1996-07-30 Bayer Corporation Low surface energy polyisocyanates and their use in one- or two-component coating compositions
US5523376A (en) 1994-12-21 1996-06-04 Bayer Corporation Coating compositions based on aldimines and polyisocyanates containing uretdione groups
US5561200A (en) 1995-05-23 1996-10-01 Bayer Corporation Blocked polyisocyanates with improved thermal stability
US5606001A (en) * 1995-09-14 1997-02-25 Bayer Corporation Polyisocyanates containing allophanate groups and optionally isocyanurate groups
DE19534624A1 (de) * 1995-09-18 1997-03-20 Bayer Ag Allophanatgruppen aufweisende Polyisocyanate auf Basis Diphenylmethandiisocyanat mit überwiegend oder vollständig blockierten Isocyanatgruppen
US5646227A (en) 1996-02-01 1997-07-08 Bayer Corporation Low surface energy polyisocyanates and their use in one- or two-component coating compositions
US5874487A (en) * 1996-11-07 1999-02-23 Ashland Inc. Foundary binder systems which contain alcohol modified polyisocyanates
US5902840A (en) * 1996-11-07 1999-05-11 Ashland Inc. Modified polymeric aromatic isocyanates having allophanate linkages
US5880174A (en) * 1996-11-07 1999-03-09 Ashland Inc. Amine modified polyisocyanates and their use in foundry binder systems
DE19728411C2 (de) * 1997-07-03 2001-09-27 Basf Coatings Ag Polyurethanharz, Verfahren zu seiner Herstellung und seine Verwendung in wäßrigen Zweikomponenten-Klarlacken
US5859163A (en) * 1997-08-22 1999-01-12 Bayer Corporation Allophanate group-containing polyisocyanates improved compatibility with aldimines
US6124375A (en) * 1997-11-07 2000-09-26 Ashland Inc. Foundry binder systems which contain alcohol modified polyisocyanates
US6228472B1 (en) * 1998-12-21 2001-05-08 Basf Corporation Process for synthesis of allophanate compounds and compositions including the product thereof
US6214470B1 (en) * 1998-12-21 2001-04-10 Basf Corporation Cathodic electrocoat composition
US6646153B1 (en) * 2000-07-19 2003-11-11 E. I. Du Pont De Nemours And Company Hydroxyl functional urethanes having a tertiary carbamate bond
US6852905B2 (en) 2001-11-15 2005-02-08 Paragon Trade Brands, Inc. Fluid handling layers made from foam and absorbent articles containing same
US20040197570A1 (en) * 2003-04-02 2004-10-07 Slack William E. Prepolymers of allophanate-modified MDI and polyoxypropylene polyol
US6797799B1 (en) 2003-04-02 2004-09-28 Bayer Materialscience Llc High 2,4′-diphenylmethane diisocyanate content prepolymers
US20050137374A1 (en) * 2003-12-17 2005-06-23 Roesler Richard R. Two-component water-borne adhesive
US20050137322A1 (en) * 2003-12-17 2005-06-23 Roesler Richard R. Silane modified two-component polyurethane coating
US20050158131A1 (en) * 2004-01-20 2005-07-21 Markusch Peter H. Geotextile/polyurethane composites based on blocked isocyanate compositions
DE102004015983A1 (de) * 2004-04-01 2005-10-20 Bayer Materialscience Ag Verfahren zur Herstellung von Polyetherallophanaten unter Verwendung von Zink-Verbindungen als Katalysatoren
DE102004015985A1 (de) * 2004-04-01 2005-10-20 Bayer Materialscience Ag Verfärbungsstabile Polyetherallophanate
DE102004015982A1 (de) * 2004-04-01 2005-10-20 Bayer Materialscience Ag Verfahren zur Herstellung von Polyisocyanat-Prepolymeren mit Allophanat-Struktureinheiten
US20050277732A1 (en) * 2004-06-14 2005-12-15 Yu Poli C Two-component coating composition
US20050288431A1 (en) * 2004-06-25 2005-12-29 Gindin Lyubov K Polyurethane dispersion prepared from a high acid functional polyester
US20050288430A1 (en) * 2004-06-25 2005-12-29 Gindin Lyubov K Polyurethane dispersions with high acid content
US20060011295A1 (en) * 2004-07-14 2006-01-19 Karsten Danielmeier Aspartic ester functional compounds
US20060014890A1 (en) * 2004-07-14 2006-01-19 Zielinski David P Polyisocyanates with improved compatibility with high hydroxyl content polyols
DE102004051026A1 (de) * 2004-10-20 2006-04-27 Bayer Materialscience Ag Kristallisationsstabile MDI-Allophanate nach einem zweistufigen Verfahren
DE102005047562A1 (de) * 2005-10-04 2007-04-05 Bayer Materialscience Ag Zweitkomponenten-Systeme für die Herstellung flexibler Beschichtungen
DE102007032666A1 (de) * 2007-07-13 2009-01-22 Bayer Materialscience Ag Allophanat- und Silangruppen enthaltende Polyisocyanate
DE102008041654A1 (de) 2007-08-31 2009-03-05 Basf Se Neue Beschichtungsmittel
US20090131581A1 (en) * 2007-11-19 2009-05-21 Wylie Amy S Aqueous, stain-resistant coating compositions
DE102009019899A1 (de) 2009-05-04 2010-11-11 Fischerwerke Gmbh & Co. Kg Klebstoffe auf Basis silanterminierter Isocyanate
DE102009019898A1 (de) 2009-05-04 2010-11-11 Fischerwerke Gmbh & Co. Kg Mehrkomponenten-Kunstmörtel auf Basis silanterminierter Harze
BR112012005122A2 (pt) 2009-09-26 2017-10-03 Segetis Inc Compostos, compostos isolados, composições, composições de polímero, método de fabricação de um composto e artigo
DE102010060443A1 (de) 2010-11-09 2012-05-10 Fischerwerke Gmbh & Co. Kg Harz für Kleb- und Beschichtungsstoffe auf Basis silanterminierter Harze mit mindestens zwei Edukten
US20140199491A1 (en) 2013-01-15 2014-07-17 Allnex Ip S.À.R.L. One-component, dual-cure conformal coating compositions
PL238230B1 (pl) 2016-09-20 2021-07-26 Politechnika Rzeszowska Im Ignacego Lukasiewicza Blokowane poliizocyjaniany, sposób ich wytwarzania i zastosowanie
EP4574874A1 (de) 2023-12-19 2025-06-25 Covestro Deutschland AG Polyisocyanatgemisch

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3248373A (en) * 1961-11-14 1966-04-26 Du Pont Urethanes containing bis (beta-hydroxyalkyl) carbamate as a chain extender
GB994890A (en) 1961-12-18 1965-06-10 Ici Ltd New organic polyisocyanates and their manufacture
DE1300277B (de) * 1964-03-07 1969-07-31 Bayer Ag Verfahren zur Herstellung von vernetzten Polyurethanen
US3368985A (en) * 1965-03-19 1968-02-13 Pittsburgh Plate Glass Co Polyurethanes produced from hydroxyl-terminated carbamates
US3491067A (en) * 1967-07-12 1970-01-20 Diamond Shamrock Corp Alkylolated polyurethane resins derived from hydroxy ethyl carbamate and their use
US3595814A (en) * 1968-11-14 1971-07-27 Jefferson Chem Co Inc Urethanes containing monocarbamate chain extenders
DE2009179C3 (de) * 1970-02-27 1974-07-11 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Allophanatpoly isocy anaten
DE2542449A1 (de) * 1975-09-24 1977-04-07 Bayer Ag Mono-methylolaether-diole
US4107151A (en) * 1976-10-28 1978-08-15 Ihara Chemical Company Co., Ltd. Process for producing urethane elastomer

Also Published As

Publication number Publication date
ES470460A1 (es) 1979-01-01
JPS543013A (en) 1979-01-11
JPS6123807B2 (enrdf_load_stackoverflow) 1986-06-07
US4177342A (en) 1979-12-04
EP0000016A1 (de) 1978-12-20
DE2725318A1 (de) 1978-12-14
IT7849672A0 (it) 1978-06-02
DE2860034D1 (en) 1980-11-13

Similar Documents

Publication Publication Date Title
EP0000016B1 (de) Verfahren zur Herstellung von Allophanatgruppen aufweisenden Polyisocyanaten und ihre Verwendung als Aufbaukomponente
EP0682012B1 (de) Verfahren zur Herstellung von Allophanatgruppen aufweisenden lichtechten Polyisocyanaten
EP0013880B1 (de) Neue Isocyanato-isocyanurate, ein Verfahren zu ihrer Herstellung sowie ihre Verwendung als Isocyanatkomponente in Polyurethan-Lacken
EP0456062B1 (de) Verfahren zur Herstellung von Isocyanuratpolyisocyanaten, die nach diesem Verfahren erhaltenen Verbindungen und ihre Verwendung
EP0000348B1 (de) Polyuret-Polyisocyanate, Verfahren zu deren Herstellung, sowie deren Verwendung bei der Herstellung von Polyurethankunststoffen.
EP0254152B1 (de) Pulverlack und seine Verwendung zur Beschichtung von Hitzeresistenten Substraten
EP0478990B1 (de) Polyisocyanatgemisch, ein Verfahren zu seiner Herstellung und seine Verwendung in Polyurethanlacken
EP0330966B1 (de) Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten
DE69215152T2 (de) Allophanat- und Isocyanuratgruppen enthaltende Polyisocyanate, Verfahren zu deren Herstellung sowie Beschichtungszusammensetzungen mit zwei Komponenten
DE69214890T3 (de) Verfahren zur Herstellung von Allophanat- und Isocyanuratgruppen enthaltenden Polyisocyanaten
EP0000963B1 (de) Isocyanuratgruppen und endständig-blockierte Isocyanatgruppen-enthaltende Verbindungen und Verfahren zu ihrer Herstellung
DE69527430T2 (de) Uretdion- und allophanatgruppen aufweisende polyisocyanate
EP0649866A1 (de) Lackpolyisocyanate und ihre Verwendung
EP0337116B1 (de) Verfahren zur Herstellung von Uretdion- und Isocyanuratgruppen aufweisenden Polyisocyanatgemischen
DE2308015B2 (de) Verfahren zur Herstellung von Polyisocyanaten mit Biuretstruktur
EP0339396A1 (de) Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten
DE1174759B (de) Verfahren zur Herstellung von Polyisocyanaten mit Biuretstruktur
DE10132016A1 (de) Cyclische Ketone als Blockierungsmittel
EP0133223B1 (de) Verfahren zur Herstellung von organischen Polyisocyanaten mit zumindest teilweise blockierten Isocyanatgruppen, die nach dem Verfahren erhältlichen Verbindungen und ihre Verwendung zur Herstellung von Polyurethanen, Einbrennlacken oder wässrigen Polyisocyanatlösungen bzw. -dispersionen
DE69727741T2 (de) Niedrigviskose Polyisocyanate hergestellt aus monomeren Triisocyanaten
EP0012973A1 (de) Verfahren zur Herstellung von Biuret- und/oder höhere Polyuretgruppen aufweisenden Polyisocyanaten, die nach diesem Verfahren erhältlichen Verbindungen, sowie ihre Verwendung als Aufbaukomponente bei der Herstellung von Polyurethankunststoffen
EP0183150B1 (de) Verfahren zur Herstellung von modifizierten Polyisocyanaten und ihre Verwendung in Polyurethananlacken
EP0727453B1 (de) Isocyanurat-Polyisocyanate auf Basis von 1,3-Diisocyanatocycloalkanen
DE2437130A1 (de) Gegen monomerenrueckspaltung stabilisiertes biuretpolyisocyanat-gemisch
EP0060476A2 (de) Verfahren zur Herstellung von N- substituierten Di- und/oder Polyurethanen

Legal Events

Date Code Title Description
PUAI Public reference made under article 153(3) epc to a published international application that has entered the european phase

Free format text: ORIGINAL CODE: 0009012

AK Designated contracting states

Kind code of ref document: A1

Designated state(s): BE DE FR GB NL

17P Request for examination filed
GRAA (expected) grant

Free format text: ORIGINAL CODE: 0009210

AK Designated contracting states

Kind code of ref document: B1

Designated state(s): BE DE FR GB NL

Designated state(s): BE DE FR GB NL

REF Corresponds to:

Ref document number: 2860034

Country of ref document: DE

Date of ref document: 19801113

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: FR

Payment date: 19810526

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: NL

Payment date: 19810630

Year of fee payment: 4

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: BE

Payment date: 19810930

Year of fee payment: 4

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: BE

Effective date: 19820601

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: NL

Effective date: 19830101

NLV4 Nl: lapsed or anulled due to non-payment of the annual fee
GBPC Gb: european patent ceased through non-payment of renewal fee
PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: FR

Free format text: LAPSE BECAUSE OF NON-PAYMENT OF DUE FEES

Effective date: 19830331

REG Reference to a national code

Ref country code: FR

Ref legal event code: ST

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: GB

Effective date: 19881117

PGFP Annual fee paid to national office [announced via postgrant information from national office to epo]

Ref country code: DE

Payment date: 19900517

Year of fee payment: 13

PG25 Lapsed in a contracting state [announced via postgrant information from national office to epo]

Ref country code: DE

Effective date: 19920401

PLBE No opposition filed within time limit

Free format text: ORIGINAL CODE: 0009261

STAA Information on the status of an ep patent application or granted ep patent

Free format text: STATUS: NO OPPOSITION FILED WITHIN TIME LIMIT