WO2007124868A1 - Feuchtigkeitshärtende kleb- und dichtstoffe - Google Patents

Feuchtigkeitshärtende kleb- und dichtstoffe Download PDF

Info

Publication number
WO2007124868A1
WO2007124868A1 PCT/EP2007/003424 EP2007003424W WO2007124868A1 WO 2007124868 A1 WO2007124868 A1 WO 2007124868A1 EP 2007003424 W EP2007003424 W EP 2007003424W WO 2007124868 A1 WO2007124868 A1 WO 2007124868A1
Authority
WO
WIPO (PCT)
Prior art keywords
prepolymers
adhesives
sealants
isocyanate
prepolymer
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.)
Ceased
Application number
PCT/EP2007/003424
Other languages
German (de)
English (en)
French (fr)
Inventor
Matthias Wintermantel
Walter Meckel
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.)
Covestro Deutschland AG
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
Priority to DE502007005473T priority Critical patent/DE502007005473D1/de
Priority to HK09110238.2A priority patent/HK1132516B/xx
Priority to EP07724361A priority patent/EP2016109B1/de
Priority to DK07724361.6T priority patent/DK2016109T3/da
Priority to JP2009508160A priority patent/JP2009535465A/ja
Priority to BRPI0711160-6A priority patent/BRPI0711160A2/pt
Priority to AU2007245910A priority patent/AU2007245910A1/en
Priority to CN2007800159622A priority patent/CN101437860B/zh
Priority to AT07724361T priority patent/ATE486096T1/de
Priority to CA002651026A priority patent/CA2651026A1/en
Publication of WO2007124868A1 publication Critical patent/WO2007124868A1/de
Anticipated expiration legal-status Critical
Ceased 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
    • C08G18/08—Processes
    • C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction 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
    • C08G18/08—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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1833—Catalysts containing secondary or tertiary amines or salts thereof having ether, acetal, or orthoester 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
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K3/00—Materials not provided for elsewhere
    • C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
    • 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
    • C08G2170/00—Compositions for adhesives
    • C08G2170/20—Compositions for hot melt adhesives
    • 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
    • C08G2190/00—Compositions for sealing or packing joints

Definitions

  • the invention relates to adhesives and sealants which cure under the influence of moisture and have good storage properties, processability which can be set within wide limits, and rapid curing.
  • Moisture-curing isocyanate-terminated prepolymers based on aromatic polyisocyanates such as TDI and preferably MDI are used depending on their isocyanate content in a wide range of industrial and do-it-yourself (DIY) applications as adhesives, sealants and coating materials.
  • DIY do-it-yourself
  • Examples include the bonding of wood, the production of sandwich constructions made of, for example, wood or aluminum panels with insulating materials such as rock wool, EPS or PUR.
  • NCO contents of about 12 to 18 wt .-%.
  • NCO-terminated prepolymers with NCO contents of about 6 to 12% by weight result in more flexible polyurethanes after curing and are accordingly suitable for producing more flexible composites, for example the production of rubber granulate compounds as floor elements for children's play areas.
  • a new class of PUR adhesives are the reactive PUR hotmelts, which, with isocyanate contents of 2 to 5% by weight, can also lead to very stiff PU depending on the polyol used.
  • the main advantage of the prepolymers is that they are one-component systems, since the reaction with water is very safe and does not require expensive stoichiometric considerations, as required in two-component systems.
  • the reaction always leads, even with a large excess of water to a cured polyurethane.
  • the reactants normally suffice for the air and / or substrate moisture present, but it can also be misted with water, in particular in the case of dense cover layers such as, for example, aluminum profiles.
  • Open time refers to the time in which the systems are still easy to process after application to the substrates to be bonded.
  • the term "workable" has to be redefined for every application.In the case of adhesives, the workability is generally defined by the time when two substrates can still be easily joined in. If the processing time is exceeded, the optimum properties, such as a repositioning, are no longer achievable.
  • the time required from the end of the processing time to the achievement of the optimum final properties should be as short as possible, because excessively long waiting times mean in practice ever higher costs, such as longer residence times in the press, etc.
  • the length of the processing time can be controlled in practice by using catalysts in principle, but at the same time by all catalysts and the shelf life of the systems (without water access) adversely affected, so that very quickly set systems also have a limited shelf life, which Logistics of products affected.
  • the limited shelf life is manifested primarily in a sharp increase in viscosity, which can go as far as gelation.
  • some catalysts allow good control of processing time, they provide an excessively long curing time of the systems. This usually means that the parts have to be stored before they can be further processed.
  • catalysts are known in polyurethane chemistry products, such as tert. aliphatic amines and / or metal catalysts.
  • metal catalysts such as dibutyltin dilaurate exhibit excellent acceleration of the water reaction with isocyanate group-containing prepolymers combined with good through-cure, but to the same extent the shelf life is adversely affected.
  • an improvement is achieved in EP-A 0 132 675 by the "blocking" of the catalyst by the addition of tosyl isocyanate, but the slightest traces of moisture are sufficient already off, this blockage, which in total, although in an improved but still insufficient storage capacity results.
  • a general disadvantage of the aromatic polyisocyanate-based prepolymers is the tendency of the final products to stain strongly under the influence of light, which is prohibitive for many applications.
  • a generally accepted principle to eliminate this drawback is the use of suitable additives, such as combinations of sterically hindered phenols and sterically hindered aliphatic amines ("HALS types"), but which are only a gradual improvement aliphatic polyisocyanates, such as, for example, hexamethylene diisocyanate, isophorone diisocyanate or 4,4'-diisocyanato-dicyclohexylmethane in the form of its steric mixtures of isomers or the above diisocyanates in the form of their derivatives.
  • HALS types sterically hindered phenols and sterically hindered aliphatic amines
  • the present invention thus provides adhesives and / or sealants based on isocyanate group-containing prepolymers based on aliphatic polyisocyanates with isocyanate contents of from 1 to 20% by weight, characterized in that the catalyst used is bis (dimethylaminoethyl) ether as Catalyst alone or in addition to other catalysts is used.
  • NCO-terminated prepolymers having isocyanate contents of 1 to 20 wt .-%, preferably 2 to 16 wt .-% are reaction products of aliphatic polyisocyanates with hydroxyl polyesters and / or hydroxyl polyethers understood as such or formulated with plasticizers, fillers, Rheologiesmitten about cure the reaction with air and / or substrate moisture to high molecular weight polyurethane polyureas.
  • aliphatic polyisocyanates in question are in particular hexamethylene diisocyanate, isophorone diisocyanate and 4,4'-diisocyanato-dicyclohexylmethane in the form of its steric mixtures of isomers to understand.
  • diisocyanates in the form of their derivatives, such as, for example, biurets, allophanates, uretdiones and trimers and mixed forms of these derivatives, are also included.
  • hydroxyl polyesters are reaction products of aliphatic dicarboxylic acids, such as adipic, azelaic, sebacic and / or dodecanedioic acid and / or aromatic dicarboxylic acid, such as ortho, iso or terephthalic acid with glycols of the ethylene glycol, diethylene glycol, 1,2 Propylene glycol, 1,4-butanediol, neopentyl glycol or hexanediol-1,6 and / or triols such as glycerine or trimethylolpropane.
  • aliphatic dicarboxylic acids such as adipic, azelaic, sebacic and / or dodecanedioic acid and / or aromatic dicarboxylic acid, such as ortho, iso or terephthalic acid
  • the reaction is a normal melt condensation, as described in Ullmann's Encyclopedia of Industrial Chemistry, "Polyester”, 4th edition, Verlag Chemie, Weinheim, 1980.
  • liquid, amorphous types having Tg values of> 20 ° C. or crystalline polyester polyols result Melting ranges of 40-90 0 C.
  • the molecular weight range of 200 to 30,000.
  • the Molekulargewichs Kunststoff of 400 to 5000 is particularly preferred.
  • polyether polyols are, in particular, the base-catalyzed addition of propylene oxide and / or ethylene oxide to starting molecules, such as, for example, water, propanediol-1,2,2,2-bis (4-hydroxyphenyl) propane, glycerol, Trimethylolpropane, ammonia, methylamine or ethylenediamine having molecular weights of 200 to 6000, in particular 200 to 5000 to call.
  • starting molecules such as, for example, water, propanediol-1,2,2,2-bis (4-hydroxyphenyl) propane, glycerol, Trimethylolpropane, ammonia, methylamine or ethylenediamine having molecular weights of 200 to 6000, in particular 200 to 5000 to call.
  • the polypropylene ether polyols available via dual metal catalysts and the construction of very high molecular weight, well-defined polyether polyols having molecular weights up to 25,000 are also possible.
  • polyether polyols with organic fillers dispersed therein, for example addition products of tolylene diisocyanate with hydrazine hydrate or copolymers of styrene and acrylonitrile.
  • polytetramethylene-n-ether glycols obtainable by polymerization of tetrahydrofuran with molecular weights of from 400 to 4000, but also hydroxyl-containing polybutadienes.
  • mixtures of the abovementioned polyols in mixture with low molecular weight polyols, such as, for example, ethylene glycol, butanediol, diethylene glycol or 1,4-butanediol.
  • the preparation of the isocyanate-terminated prepolymers is carried out by known methods by the polyols with a stoichiometric excess of aliphatic polyisocyanates at temperatures of 30 to 150 0 C, preferably 60 to 140 0 C are reacted. This can be done discontinuously in boilers or continuously in boiler cascades or via mixers.
  • the hydroxyl compounds are reacted with a high excess of disaccharides and that the monomeric disocyanate still present is removed by known techniques, for example by means of a thin film evaporator at elevated temperature and reduced pressure is removed from the prepolymer.
  • prepolymers with a low monomer content are obtained which, depending on the residual monomer content, are in some cases no longer subject to labeling.
  • the catalyst bis (dimethylaminoethyl) ether is added to the prepolymers before, during or preferably after the completion of prepolymer formation.
  • the added amount of this catalyst depends on the desired processing time. In general, amounts of 0.02 to 3.0 wt .-%, preferably 0.1 to 2.0 wt .-%, particularly preferably 0.5 to 1.5 wt .-%, based on the prepolymer, out.
  • solvents, fillers, dyes and rheological aids can be added to the prepolymers.
  • fillers which may be mentioned are chalk, barite, but also fibrous fillers, such as polyamide or polyacrylonitrile fibers.
  • fibrous fillers such as polyamide or polyacrylonitrile fibers.
  • rheology aids in addition to the customary industrial additives such as aerosils, bentonites or hydrogenated castor oil, are also low molecular weight
  • Called amines which in combination with polyisocyanates very rapidly build up an intrinsic viscosity. With all these additives, it is important to be absolutely free from moisture, as this would lead to premature reaction in the container.
  • the order of the adhesives, sealants for example, by squeegee spraying, Pinsem or in a more compact form in the form of a bead.
  • a good way of assessing the different curing phases of such systems is, for example, with the aid of commercially available equipment, such as Drying Recorder BK 10 (The Mickle Laboratory Engineering Co. Ltd.), which is widely used in the paint, adhesive and sealant industries .
  • a needle loaded with a weight if necessary, is guided at a constant speed through a thin film of the prepolymer to be examined on a support (eg glass plate).
  • Three phases are observed, which by definition are termed "processing time” and "curing time”.
  • processing time Three phases are observed, which by definition are termed "processing time” and "curing time”.
  • the needle passes through the liquid film and the track of the needle is more or less complete, which is correlated with processing time.
  • the end of processing time also referred to as skinning time, open time, or contact tack time, is indicated by the first appearance of a permanent trace of the needle.
  • the practitioner desires the time between the end of the processing time and the achievement of the curing time as short as possible.
  • the invention also relates to the use of such catalyzed prepolymers as adhesives and / or sealants, in which it depends on the curing of the aliphatic isocyanate groups with moisture.
  • Possible applications include gluing wood bodies, such as finger joints, glulam beams or beams. Likewise, the bonding of
  • the prepolymer shows a constant NCO value of 31.5% at the end of the reaction time of 6 hours.
  • the prepolymer is then freed at 160 0 C and 0.1 mm Hg over a short path evaporator largely from the excess monomers.
  • the prepolymer shows a constant NCO value of at the end of the reaction time of 9 hours
  • the prepolymer is then freed at 180 0 C and 0.1 mm Hg over a short path evaporator largely from the excess monomers.
  • a film is applied to a previously cleaned with ethyl acetate glass plate and immediately loaded into the Drying Recorder.
  • the needle is loaded with 10 g and moves over a period of 360 minutes over a distance of 35 cm.
  • the Drying Recorder is located in a climate room at 23 ° C and 50% rel. Humidity.
  • the cure time is given at the time of disappearance of the permanent trace of the needle from the film.
  • the prepolymer was coated on one side and the test specimens (50x20x5 mm) for 10x20 mm overlapping in the press with 5 bar at 23 0 C and 50% rel. Kept moist. The bond strength was then measured in the tensile shear test (10 test specimens in each case).
  • the adhesives catalyzed according to the invention already give good bond strengths after a short time.
  • 100 g of the prepolymer from Example 2 are mixed with various commercially available catalysts in such a way that a processing time (visual appearance of a permanent trace of the needle in the film) of about 25 to 60 minutes results with the Drying Recorder.
  • the cure time is given at the time of disappearance of the permanent trace of the needle from the film.
  • Example 7 As can be seen from the table, with the amine catalysts (Example 6 D and 6 G 5 or 6 H) at doses of 1% by weight and less greatly reduced processing times are certainly achieved.
  • Example 7 As can be seen from the table, with the amine catalysts (Example 6 D and 6 G 5 or 6 H) at doses of 1% by weight and less greatly reduced processing times are certainly achieved.
  • Example 7
  • the storage stability is tested at 100 ° C. after 4, 24, 48 and 72 hours.
  • the storage stability is tested at 100 ° C. after 4, 24, 48 and 72 hours.
  • the curing characteristic is determined by means of the "kinking test.” For this purpose, a 0.1 mm thick prepolymer film is laced onto a glass plate and the solidified prepolymer is subjected to a kink test after certain times (at 23 ° C. and 50 relative atmospheric humidity) 180 ° C. Only a largely reacted polymer will survive the test Unreacted polymers break because no sufficiently high molecular weight has yet been built up.
  • the adhesive which has been heated to 130 ° C., is applied with a doctor blade to beech wood test specimens and bonded immediately with a PVC film.
  • the heated at 130 0 C adhesive is applied to one side beech wood and immediately bonded to another beech wood and torn in the shear tension.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Liquid Crystal (AREA)
  • Electroluminescent Light Sources (AREA)
  • Sealing Material Composition (AREA)
PCT/EP2007/003424 2006-05-02 2007-04-19 Feuchtigkeitshärtende kleb- und dichtstoffe Ceased WO2007124868A1 (de)

Priority Applications (10)

Application Number Priority Date Filing Date Title
DE502007005473T DE502007005473D1 (de) 2006-05-02 2007-04-19 Feuchtigkeitshärtende kleb- und dichtstoffe
HK09110238.2A HK1132516B (en) 2006-05-02 2007-04-19 Moisture-curing adhesives and sealants
EP07724361A EP2016109B1 (de) 2006-05-02 2007-04-19 Feuchtigkeitshärtende kleb- und dichtstoffe
DK07724361.6T DK2016109T3 (da) 2006-05-02 2007-04-19 Fugtighedshærdende klæbe- og tætningsstoffer
JP2009508160A JP2009535465A (ja) 2006-05-02 2007-04-19 湿分硬化性の接着剤およびシーラント
BRPI0711160-6A BRPI0711160A2 (pt) 2006-05-02 2007-04-19 pré-polìmeros contendo grupos isocianato que se curam por umidade, uso dos mesmos e substratos aderidos ou selados com adesivos e selantes
AU2007245910A AU2007245910A1 (en) 2006-05-02 2007-04-19 Moisture-curing adhesives and sealants
CN2007800159622A CN101437860B (zh) 2006-05-02 2007-04-19 水分固化粘合剂和密封剂
AT07724361T ATE486096T1 (de) 2006-05-02 2007-04-19 Feuchtigkeitshärtende kleb- und dichtstoffe
CA002651026A CA2651026A1 (en) 2006-05-02 2007-04-19 Moisture-hardening adhesives and sealants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006020605.3 2006-05-02
DE102006020605A DE102006020605A1 (de) 2006-05-02 2006-05-02 Feuchtigkeitshärtende Kleb- und Dichtstoffe

Publications (1)

Publication Number Publication Date
WO2007124868A1 true WO2007124868A1 (de) 2007-11-08

Family

ID=38308748

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2007/003424 Ceased WO2007124868A1 (de) 2006-05-02 2007-04-19 Feuchtigkeitshärtende kleb- und dichtstoffe

Country Status (13)

Country Link
US (1) US20070260031A1 (enExample)
EP (1) EP2016109B1 (enExample)
JP (1) JP2009535465A (enExample)
KR (1) KR20090018081A (enExample)
CN (1) CN101437860B (enExample)
AT (1) ATE486096T1 (enExample)
AU (1) AU2007245910A1 (enExample)
BR (1) BRPI0711160A2 (enExample)
CA (1) CA2651026A1 (enExample)
DE (2) DE102006020605A1 (enExample)
DK (1) DK2016109T3 (enExample)
ES (1) ES2354389T3 (enExample)
WO (1) WO2007124868A1 (enExample)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009144280A1 (de) * 2008-05-29 2009-12-03 Henkel Ag & Co. Kgaa Reaktive klebstoffe mit sehr geringem gehalt an monomeren diisocyanaten
EP2386586A1 (de) * 2010-04-27 2011-11-16 Henkel AG & Co. KGaA PU-Klebstoff mit Fließgrenze
CN102471437A (zh) * 2009-08-11 2012-05-23 拜尔材料科学股份公司 具有好的储存稳定性的含异氰酸酯基团的预聚物

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR3075213B1 (fr) * 2017-12-20 2020-08-28 Bostik Sa Procede de preparation d'une composition comprenant un polyurethane a terminaisons nco
CN111741992B (zh) * 2018-02-21 2022-10-28 Dic株式会社 湿气固化型聚氨酯热熔树脂组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4511626A (en) * 1982-09-09 1985-04-16 Minnesota Mining And Manufacturing Company One-part moisture-curable polyurethane adhesive, coating, and sealant compositions
EP0472278A1 (en) * 1990-07-20 1992-02-26 Lord Corporation Non-yellowing polyurethane adhesives
DE4129936A1 (de) * 1990-09-10 1992-03-12 San Apro Ltd Feuchtigkeitshaertbare polyurethanharzzusammensetzung und ein daraus hergestellter verband
EP1595902A1 (de) * 2004-05-10 2005-11-16 Sika Technology AG Polyurethanzusammensetzung mit hoher Frühfestigkeit

Family Cites Families (11)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3330782A (en) * 1963-11-12 1967-07-11 Union Carbide Corp Beta-(n, n-dimethylamino)alkyl ethers as catalysts for isocyanate reactions
US3939123A (en) * 1974-06-18 1976-02-17 Union Carbide Corporation Lightly cross-linked polyurethane hydrogels based on poly(alkylene ether) polyols
DE3827224C3 (de) * 1988-08-11 2003-09-25 Degussa Schmelzklebeverfahren
US5866656A (en) * 1995-06-07 1999-02-02 National Starch And Chemical Investment Holding Corporation Polyurethane hotmelt adhesives with reactive acrylic copolymers
CA2214311A1 (en) * 1996-09-06 1998-03-06 Air Products And Chemicals, Inc. Hot melt adhesives comprising low free monomer, low oligomer isocyanate prepolymers
US5965685A (en) * 1998-01-14 1999-10-12 Reichhold Chemicals, Inc. Rapid curing aliphatic hot melt adhesive
US6482878B1 (en) * 2000-04-21 2002-11-19 National Starch And Chemical Investment Holding Corporation Polyurethane hotmelt adhesives with acrylic copolymers and thermoplastic resins
MXPA02011491A (es) * 2001-12-06 2003-06-30 Rohm & Haas Adhesivo de fusion en caliente.
DE10161386A1 (de) * 2001-12-14 2003-06-18 Bayer Ag Monomerenarme NCO-haltige Prepolymere auf der Basis von Isophorondiisocyanat
RU2004122092A (ru) * 2001-12-18 2006-01-20 Хенкель Коммандитгезелльшафт Ауф Акциен (DE) Способ получения обедненных мономером форполимеров полиуретана
US20030203771A1 (en) * 2002-04-26 2003-10-30 Ronald Rosenberg Polyurethane elastomers from HDI prepolymers with reduced content of free HDI monomers

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4511626A (en) * 1982-09-09 1985-04-16 Minnesota Mining And Manufacturing Company One-part moisture-curable polyurethane adhesive, coating, and sealant compositions
EP0472278A1 (en) * 1990-07-20 1992-02-26 Lord Corporation Non-yellowing polyurethane adhesives
DE4129936A1 (de) * 1990-09-10 1992-03-12 San Apro Ltd Feuchtigkeitshaertbare polyurethanharzzusammensetzung und ein daraus hergestellter verband
EP1595902A1 (de) * 2004-05-10 2005-11-16 Sika Technology AG Polyurethanzusammensetzung mit hoher Frühfestigkeit

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2009144280A1 (de) * 2008-05-29 2009-12-03 Henkel Ag & Co. Kgaa Reaktive klebstoffe mit sehr geringem gehalt an monomeren diisocyanaten
CN102471437A (zh) * 2009-08-11 2012-05-23 拜尔材料科学股份公司 具有好的储存稳定性的含异氰酸酯基团的预聚物
CN102471437B (zh) * 2009-08-11 2014-07-30 拜尔材料科学股份公司 具有好的储存稳定性的含异氰酸酯基团的预聚物
EP2386586A1 (de) * 2010-04-27 2011-11-16 Henkel AG & Co. KGaA PU-Klebstoff mit Fließgrenze

Also Published As

Publication number Publication date
CN101437860B (zh) 2011-11-16
DE502007005473D1 (de) 2010-12-09
DK2016109T3 (da) 2011-02-14
AU2007245910A1 (en) 2007-11-08
US20070260031A1 (en) 2007-11-08
EP2016109A1 (de) 2009-01-21
DE102006020605A1 (de) 2007-11-08
ES2354389T3 (es) 2011-03-14
CA2651026A1 (en) 2007-11-08
BRPI0711160A2 (pt) 2011-08-23
ATE486096T1 (de) 2010-11-15
CN101437860A (zh) 2009-05-20
HK1132516A1 (en) 2010-02-26
EP2016109B1 (de) 2010-10-27
KR20090018081A (ko) 2009-02-19
JP2009535465A (ja) 2009-10-01

Similar Documents

Publication Publication Date Title
EP2791153B1 (de) Bismuthaltiger katalysator für polyurethan-zusammensetzungen
EP1674546B1 (de) Feuchthärtende Zusammensetzung und Schmelzklebstoff
EP2038360B1 (de) Feuchtigkeitsreaktiver schmelzklebstoff mit erhöhter offenzeit
EP2791156B1 (de) Metall-komplexverbindungen als katalysatoren für polyurethan-zusammensetzungen
EP2220034B1 (de) Aromatische aldimine und aldimin enthaltende polyurethanzusammensetzungen
EP2464677B1 (de) Isocyanatgruppen enthaltende prepolymere mit guter lagerstabilität
EP2791145B1 (de) Zink(ii)-komplexverbindungen als katalysatoren für polyurethan-zusammensetzungen
EP2016109B1 (de) Feuchtigkeitshärtende kleb- und dichtstoffe
WO2017009310A1 (de) Polyurethan-heissschmelzklebstoff, enthaltend dialdimine mit verbesserter haftung auf edelstahl
EP2791155B1 (de) Eisen(iii)-komplexverbindungen als katalysatoren für polyurethan-zusammensetzungen
EP4588948A1 (en) Moisture curable hot-melt adhesive having high transparency
EP2791154B1 (de) Dioxomolybdän(vi)-komplexverbindungen als katalysatoren für polyurethan-zusammensetzungen
HK1132516B (en) Moisture-curing adhesives and sealants
HK1167418A (en) Isocyanate group-containing prepolymers having good storage stability
HK1167418B (en) Isocyanate group-containing prepolymers having good storage stability

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 07724361

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 2007724361

Country of ref document: EP

WWE Wipo information: entry into national phase

Ref document number: 2651026

Country of ref document: CA

WWE Wipo information: entry into national phase

Ref document number: 200780015962.2

Country of ref document: CN

Ref document number: 9166/DELNP/2008

Country of ref document: IN

NENP Non-entry into the national phase

Ref country code: DE

WWE Wipo information: entry into national phase

Ref document number: 2009508160

Country of ref document: JP

WWE Wipo information: entry into national phase

Ref document number: 2007245910

Country of ref document: AU

WWE Wipo information: entry into national phase

Ref document number: 1020087029355

Country of ref document: KR

ENP Entry into the national phase

Ref document number: 2007245910

Country of ref document: AU

Date of ref document: 20070419

Kind code of ref document: A

ENP Entry into the national phase

Ref document number: PI0711160

Country of ref document: BR

Kind code of ref document: A2

Effective date: 20081103