EP2160428A1 - Mélanges de polyisocyanates - Google Patents

Mélanges de polyisocyanates

Info

Publication number
EP2160428A1
EP2160428A1 EP08759135A EP08759135A EP2160428A1 EP 2160428 A1 EP2160428 A1 EP 2160428A1 EP 08759135 A EP08759135 A EP 08759135A EP 08759135 A EP08759135 A EP 08759135A EP 2160428 A1 EP2160428 A1 EP 2160428A1
Authority
EP
European Patent Office
Prior art keywords
isocyanate
polyisocyanate
content
polyisocyanate mixtures
mpa
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Withdrawn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
EP08759135A
Other languages
German (de)
English (en)
Inventor
Christian Wamprecht
Christos Karafilidis
Peter Reichert
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 Intellectual Property GmbH
Original Assignee
Bayer MaterialScience 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 MaterialScience AG filed Critical Bayer MaterialScience AG
Publication of EP2160428A1 publication Critical patent/EP2160428A1/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Withdrawn legal-status Critical Current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
    • C08G18/28—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
    • C08G18/302—Water
    • C08G18/307—Atmospheric humidity
    • 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
    • C08G18/12—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step using two or more compounds having active hydrogen in the first polymerisation step
    • 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
    • C08G18/48—Polyethers
    • C08G18/4804—Two or more polyethers of different physical or chemical nature
    • C08G18/482—Mixtures of polyethers containing at least one polyether containing nitrogen
    • 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
    • C08G18/48—Polyethers
    • C08G18/50—Polyethers having heteroatoms other than oxygen
    • C08G18/5021—Polyethers having heteroatoms other than oxygen having nitrogen
    • 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
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
    • C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
    • C09J175/04—Polyurethanes
    • C09J175/08—Polyurethanes from polyethers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00—Stock material or miscellaneous articles
    • Y10T428/31504—Composite [nonstructural laminate]
    • Y10T428/31551—Of polyamidoester [polyurethane, polyisocyanate, polycarbamate, etc.]

Definitions

  • the invention relates to polyisocyanate mixtures, their preparation by reaction of aromatic polyisocyanate mixtures with special nitrogen-containing polyetherol mixtures and their use as isocyanate component for the production of moisture-curing adhesives.
  • Moisture-curing adhesives and their preparation belong to the general state of the art and have been described many times in the literature. All prepolymers containing isocyanate groups, which are not stored under complete exclusion of moisture, lose isocyanate groups over time due to reaction with atmospheric moisture. Temperature stress promotes this process significantly. On the surface, this reaction proceeds rapidly, the indiffusion ms interior of z. As moldings, foams or adhesive and sealant layers can take long periods. As long as this reaction takes place, the molecular weight or the crosslinking density increases, correspondingly, the physical properties change.
  • the formulations are often external catalysts such.
  • organic tin compounds dibutyltin dilaurate
  • aminic accelerator Dimorpholmodiethylether
  • Starting products contain prepolymers containing isocyanate groups. These prepolymers are prepared by reacting a polyol mixture consisting of 90-100% by weight of an aminopolyamine. ether and / or polyester alcohol consists, with organic polyisocyanates and other additives, such. B. propellants in pressure vessels, such. As aerosol cans obtained. When relaxing to atmospheric pressure, with the help of z. As a valve foams the mixture and cures quickly under the influence of humidity to a dimensionally stable closed-cell polyurethane foam. However, such products are not suitable for the formulation of moisture-curing adhesives.
  • Crystallization tendency and are suitable for the production of cellular or compact polyurethane plastics.
  • adhesives such products are not suitable.
  • EP-A 1 471 088 describes PUR Formuher Institute based on polyisocyanates
  • Polyether polyols having at least one aromatic and / or aliphatic NH 2 - or NHR-group-containing starter which immediately or very quickly lead to a good compatibility when mixing the polyol with the polyisocyanates, so that the stirring time in comparison to systems of the prior Technology can be shortened.
  • This good compatibility is particularly desirable in the production of PUR casting resins and casting compounds for moldings which are produced by curing in a release-prepared mold.
  • DE-A 1 922 626 describes a process for the preparation of storage-stable, moisture-fast, one-component polyurethane-based one-component systems.
  • the polyurethane isocyanates based on amine-initiated polyethers obtainable by this process according to the Offenbahrungen and examples are prepared in considerable amounts of suitable paint solvents (60 wt .-% solvent, 40 wt .-% polymer), such as esters, ketones or chlorinated hydrocarbons, and are usable as a binder in emulsion paint systems.
  • suitable paint solvents 60 wt .-% solvent, 40 wt .-% polymer
  • suitable solvents such as esters, ketones or chlorinated hydrocarbons
  • Adhesives can not be produced by this method.
  • WO 1995/10555 describes moisture-curing adhesive compositions consisting of the reaction product of a polyisocyanate and an isocyanate-reactive component containing at least one aliphatic, amine-started polyol with an ethylene oxide content of at least 1%.
  • Isocyanate-containing prepolymers based on polyethers with ethylene oxide units have a particularly high affinity for moisture. This can lead to increased blistering during the curing of the adhesives. This blistering is detrimental to the adhesion bond.
  • DE-A 10 237 649 describes a 1K polyurethane adhesive which contains at least one polyisocyanate prepolymer and at least one ammopolyether polyol, the molar ratio of ether groups to amine nitrogen in the aminoether polyol being from 7 to 30.
  • the proportion of aminopolyetherpolyols in the inventive adhesive is very low and is only 0.2 to 4.0 wt .-%. This small proportion leads under dimorphohnodiethylether catalysis already to a halving of the pressing time in the bonding of beech wood.
  • the open time that is to say the processing time
  • DE-A 10 304 153 describes a polyurethane prepolymer which has as constituent components a mixture of polyisocyanates having symmetrical and asymmetric isocyanate groups and a mixture of polyethers having functionalities ⁇ 2.5 and> 2.5, the proportion of polyisocyanates having symmetrical isocyanate groups is higher than that of polyisocyanates with asymmetric polyisocyanates.
  • the inventive value of this patent application should then be that the claimed prepolymers are particularly bright color. This issue is highly doubtful because the color of prepolymers does not depend on the isomer composition of polyisocyanates nor on the functionality of polyol components. This fact was taken into account in the issue of the corresponding EP patent EP-B 1 490 418, at least the molecular weights of the polyether components being severely limited.
  • EP-A 1 072 620 describes a low-solvent adhesive composition consisting of up to 99.999% by weight of an isocyanate group-containing prepolymer, 0 to 20% by weight of additives and auxiliaries and 0.001 to 10% by weight of at least one morphine derivative as activator.
  • composition of the claimed prepolymer is chosen to be very broad, thus giving no specific characteristic of the resulting adhesive compositions. Furthermore, a Morpholmde ⁇ vat is absolutely necessary, which has a limiting effect, adversely affect the storage stability and can lead to compatibility problems.
  • EP-A 1 072 621 describes fibrous adhesive compositions based on the adhesive composition according to EP-A 1 072 620 and 0.1 to 20% by weight of a filler containing at least one fiber, with the difference that no morpholine indenate, but a fiber-containing filler is mandatory.
  • the object of the present invention was to provide polyisocyanate mixtures for adhesive applications which do not have the disadvantages of the prior art. They should have a low viscosity, improved storage stability, and without the addition of a separate activator, a fast film formation time and the shortest possible film drying time, a high initial strength after a short adhesive time and a high final strength after the shortest possible curing time.
  • the invention therefore polyisocyanate mixtures consisting of
  • polyisocyanate mixtures have isocyanate contents of 12 to 20 wt .-%, Isocyanatfunktionaht2011en of> 2.4, viscosities of ⁇ 10,000 mPa-s at 25 ° C and a shear rate of 80 l / s and that they contain:
  • the invention also provides a process for the preparation of the erf ⁇ ndungshielen
  • Prepolymers by reaction of special aromatic polyisocyanate mixtures with special nitrogen-containing polyetherol mixtures and their use as isocyanate component in moisture-curing adhesives.
  • the viscosity of the polyisocyanate mixtures according to the invention is 25 ° C. and one
  • the isocyanate content of the polyisocyanate mixtures according to the invention is in the range from 12 to 20% by weight, preferably from 13 to 19% by weight and more preferably in the range from 14 to 18% by weight.
  • the average isocyanate functionality of the polyisocyanate mixtures according to the invention is> 2.20, preferably> 2.40 and more preferably> 2.60.
  • the polyisocyanate components a) and b) are initially charged in a reaction vessel and are heated at temperatures in the range from 10.degree
  • the components a) to d) are preferably used in the proportions that the properties of the polyisocyanate mixture described above, in particular the viscosity, the isocyanate content and the functionality are achieved.
  • the polyisocyanate component a) consists of at least one aromatic polyisocyanate mixture based on diphenylmethane isocyanate having at least 38.0% isocyanate groups in the 4,4'-position, between 0.0 and at most 60.0% in the 2,4'-position and between 0 , 0 and a maximum of 2.0% in 2,2'-position, with a functionality of 2.0.
  • the isocyanate content holds at> 33.0 wt .-%, preferably at> 33.2 wt .-%, particularly preferably at> 33.4 wt% and particularly preferably at> 33.5 wt .-%.
  • the polyisocyanate component b) consists of at least one polyisocyanate mixture based on diphenylmethane isocyanate with a proportion of 4,4'-isomers of ⁇ 50%, preferably ⁇ 48%, particularly preferably ⁇ 46% and very particularly preferably ⁇ 44%; a proportion of 2,4'-isomers in the range of 10 to 15%, more preferably 11 to 14% and particularly preferably 11.5 to 13.5%; and a proportion of 2,2'-isomers in the range of 0.1 to 5%, preferably 1 to 4% and particularly preferably 1.5 to 3.5%; an isocyanate content of between 30 and 33% by weight, particularly preferably 31 and 32% by weight; and a functionality> 2.0, preferably> 2.2, more preferably> 2.4 and very particularly preferably> 2.5.
  • the polyol component c) consists of at least one ammo phenomenon clar polyether based on propylene oxide having an OH number in the range of 40 to 80 mg KOH / g, preferably 45 to 75 and particularly preferably 50 to 70 and a functionality of at least 2.0, preferably 2.0 to 4.0, more preferably 2.0 to 3.0, and most preferably 2.0 to 2.5.
  • starter molecules for the polyol component c) are polyols, such as, for example, ethylene glycol, propylene glycol, 1,4-butanediol, polyols, such as. As Glyce ⁇ n, temethylolpropane or pentaerythritol and water into consideration.
  • the polyol component d) consists of at least one amino group-containing polyether based on propylene oxide having an OH number in the range of 40 to 80 mg KOH / g, preferably 45 to 75 and particularly preferably 50 to 70, a functionality of 4.0 and an amine content in the range of 0.50 to 1.00, preferably 0.56 to 0.94 and more preferably 0.62 to 0.88 wt .-%.
  • diamines such as.
  • ethylenediamine hexamethylenediamine, isophoronediamine and 4,4'-diaminodicyclohexylmethane into consideration.
  • the isocyanate components are preferably initially charged in a reaction vessel under an inert gas atmosphere and the polyol components are metered in.
  • the reaction temperatures are in the range of 20 to 120 0 C, preferably 30 to 110 0 C and more preferably 40 to 100 0 C.
  • a possibly occurring exothermic reaction is advantageously carried off as cooling capture the reaction between the isocyanate groups of components a) and b) with the hydroxyl groups of components c) and d) at constant temperature.
  • the reaction is complete when the desired isocyanate contents or viscosities of the polyisocyanate mixtures according to the invention are reached.
  • polyisocyanate mixtures according to the invention consisting of
  • the polyisocyanate mixtures according to the invention are characterized by a rapid drying at room temperature and a very early bond strength, so that catalysts and accelerators can be completely dispensed with. For this reason, the polyisocyanate mixtures have extremely good storage stability, even at elevated temperatures of up to 80 ° C. Furthermore, the viscosity is very favorable for the application.
  • the viscosity of the polyisocyanate mixtures according to the invention is 25 ° C.
  • the film-forming time of the adhesives prepared from the polyisocyanate mixtures according to the invention has a thickness of 250 .mu.m and Khmabedmgungen of 23 ° C and 50% relative humidity between 30 and 75 min, preferably between 35 and 65 min and more preferably between 40 and 60 min.
  • the film drying time of the adhesives prepared from the polyisocyanate mixtures according to the invention has a layer thickness of 250 ⁇ m and climatic conditions of 23 ° C. and 50% relative humidity at ⁇ 100 min, preferably ⁇ 90 mm and particularly preferably ⁇ 80 min.
  • the resulting polyol mixture is within about 30 minutes of a mixture of 923 g of a polyisocyanate based on diphenylmethane
  • MDI polyisocyanate
  • NCO NCO
  • 2,2'-MDI 2.3%
  • 2,4'-MDI 12.6%
  • 4,4'-MDI 42.4%
  • a content of 2, 1% 4'-MDI and a content of 4,4'-MDI of 99% and a viscosity of 4 mPa-s (25 ° C) added.
  • the resulting polyol mixture is within about 30 minutes of a mixture of 923 g of a polyisocyanate based on diphenylmethane
  • MDI polyisocyanate based on MDI with an NCO content of 33.6 wt .-%, a content of 2, 4'-MDI of 56.0 wt .-% and a content of 4,4'-MDI of 43.4 wt .-% and a viscosity of 4 mPa ⁇ s (25 ° C) added.
  • the resulting polyol mixture is within about 30 minutes of a mixture of 1035 g of a polyisocyanate based on diphenylmethane (MDI) with an NCO content of 31.5 wt .-%, a content of 2,2'-MDI of 2.3 weight
  • % a content of 2,4'-MDI of 12.6 wt .-% and a content of 4,4'-MDI of 42.4 wt .-%, and a viscosity of 90 mPa ⁇ s at 25 ° C. and HO g of a polyisocyanate based on MDI having an NCO content of 33.6 wt .-%, a content of 2,4'-MDI of 1 wt .-% and a content of 4,4'-MDI of 99 wt .-% and a viscosity of 4 mPa ⁇ s (25 ° C) added. Then it is heated to 80 0 C taking advantage of a possibly occurring exothermic reaction.
  • the resulting polyol mixture is within about 30 minutes of a mixture of 1035 g of a polyisocyanate based on diphenylmethane (MDI) with an NCO content of 31.5 wt .-%, a content of 2,2'-MDI of 2.3 % By weight, a content of 2,4'-MDI of 12.6 wt .-% and a content of 4,4'-MDI of 42.4 Wt .-%, and a viscosity of 90 mPa s at 25 ° C and 110 g of a polyisocyanate based on MDI with an NCO content of 33.6 wt .-%, a content of 2,4'-MDI of 56, 0% and a content of 4,4'-MDI of 43.4 wt .-% and a viscosity of 4 mPa-s (25 ° C) added.
  • MDI diphenylmethane
  • the resulting polyol mixture is within about 30 minutes of a mixture of 1140 g of a polyisocyanate based on diphenylmethane (MDI) with an NCO content of 31.5 wt .-%, a content of 2,2'-MDI of 2.3 weight
  • Polyol mixture is within about 30 minutes of a mixture of 1176 g of a polyisocyanate based on diphenylmethane (MDI) with an NCO content of 31.5 Wt .-%, a content of 2,2'-MDI of 2.3 wt .-%, a content of 2,4'-MDI of 12.6 wt .-% and a content of 4,4'-MDI of 42.4 wt .-%, and a viscosity of 90 mPa-s at 25 ° C added. Then it is heated to 80 0 C taking advantage of a possibly occurring exothermic reaction. It is stirred at 80 0 C until the isocyanate content is constant.
  • MDI diphenylmethane
  • the film formation time (FBZ, dry-hard time) and film dry times (FTZ, set-to-touch time) according to ASTM D 5895 in the linear drying recorder and the viscosity at 25 ° C and a shear rate of 80 l / s (rotational viscometer with coaxial cylinders, DIN 53019).
  • the Lagerstabiht2011 was measured at 70 0 C in the form of viscosity increase over time.
  • the polyisocyanate mixture is considered storage stabü when the viscosity within 14 days storage at 70 0 C is less than doubled.
  • the inventive polyisocyanate mixtures according to Examples 1 to 4 have a low viscosity of ⁇ 7,000 mPa s at 25 0 C and a shear rate of 80 l / s, a good Lagerstabiht2011 and a high reactivity, which is reflected in short film formation and film drying times .
  • the polyisocyanate mixture from Example 5 also has a low viscosity and a good storage stability, but the film drying time is significantly longer than in the inventive polyisocyanate mixtures.
  • the polyisocyanate mixture of Example 6 provides very short film formation and film drying times, however, the viscosity is very high and Lagerstabiht2011 not given.

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  • 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)

Abstract

L'invention concerne des mélanges de polyisocyanates, leur fabrication par réaction de mélanges de polyisocyanates aromatiques avec des mélanges spéciaux de polyéthérol contenant de l'azote, ainsi que leur utilisation en tant que composant isocyanate pour la fabrication d'adhésifs durcissant à l'humidité.
EP08759135A 2007-06-22 2008-06-10 Mélanges de polyisocyanates Withdrawn EP2160428A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE200710028922 DE102007028922A1 (de) 2007-06-22 2007-06-22 Polyisocyanatmischungen
PCT/EP2008/004608 WO2009000405A1 (fr) 2007-06-22 2008-06-10 Mélanges de polyisocyanates

Publications (1)

Publication Number Publication Date
EP2160428A1 true EP2160428A1 (fr) 2010-03-10

Family

ID=39683862

Family Applications (1)

Application Number Title Priority Date Filing Date
EP08759135A Withdrawn EP2160428A1 (fr) 2007-06-22 2008-06-10 Mélanges de polyisocyanates

Country Status (5)

Country Link
US (1) US7985479B2 (fr)
EP (1) EP2160428A1 (fr)
DE (1) DE102007028922A1 (fr)
TW (1) TW200918603A (fr)
WO (1) WO2009000405A1 (fr)

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Publication number Priority date Publication date Assignee Title
WO2008094239A1 (fr) * 2007-01-30 2008-08-07 Dow Global Technologies, Inc. Polyols initiés par une amine et mousse de polyuréthane rigide fabriquée à partir de ces derniers
DE102010019504A1 (de) 2010-05-06 2011-11-10 Bayer Materialscience Ag Polyisocyanatprepolymere und deren Verwendung
EP3960783A1 (fr) 2020-09-01 2022-03-02 Covestro Deutschland AG Prépolymères à terminaison isocyanate à base de copolymères séquencés polyoxyméthylène-polyoxyalkylène, leur procédé de fabrication et leur utilisation
CN116376504A (zh) * 2023-03-17 2023-07-04 西安工程大学 利用废弃pet瓶制备功能性材料的方法

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GB8701372D0 (en) * 1987-01-22 1987-02-25 Bp Chem Int Ltd Storage stable isocyanate prepolymers
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EP0796880A2 (fr) 1996-03-21 1997-09-24 Bayer Ag Composition de revêtement à un composant durcissable par de l'humidité
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WO2003016368A1 (fr) * 2001-08-16 2003-02-27 Henkel Kommanditgesellschaft Auf Aktien Colle polyurethane 1 k a prise rapide
ES2276044T3 (es) * 2002-02-08 2007-06-16 Henkel Kommanditgesellschaft Auf Aktien Pegamento de poliuretano de un solo componente de color neutro.
US6908979B2 (en) * 2002-11-18 2005-06-21 Huntsman International Llc Polyurethane elastomer gels
DE10318740A1 (de) 2003-04-25 2004-11-11 Bayer Materialscience Ag Polyurethan-Formulierungen und ihre Verwendung

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Also Published As

Publication number Publication date
WO2009000405A1 (fr) 2008-12-31
TW200918603A (en) 2009-05-01
US7985479B2 (en) 2011-07-26
DE102007028922A1 (de) 2008-12-24
US20080318060A1 (en) 2008-12-25

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