WO2011069954A1 - Produits d'étanchéité - Google Patents

Produits d'étanchéité Download PDF

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Publication number
WO2011069954A1
WO2011069954A1 PCT/EP2010/068952 EP2010068952W WO2011069954A1 WO 2011069954 A1 WO2011069954 A1 WO 2011069954A1 EP 2010068952 W EP2010068952 W EP 2010068952W WO 2011069954 A1 WO2011069954 A1 WO 2011069954A1
Authority
WO
WIPO (PCT)
Prior art keywords
alkoxysilane
mixture
modified polyurethanes
mol
several
Prior art date
Application number
PCT/EP2010/068952
Other languages
German (de)
English (en)
Inventor
Evelyn Peiffer
Mathias Matner
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 CN2010800562013A priority Critical patent/CN102741308A/zh
Priority to US13/514,742 priority patent/US8981030B2/en
Priority to EP10790748A priority patent/EP2510029A1/fr
Priority to JP2012542488A priority patent/JP2013513674A/ja
Publication of WO2011069954A1 publication Critical patent/WO2011069954A1/fr

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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/48—Polyethers
    • C08G18/4825—Polyethers containing two hydroxy 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
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/2805—Compounds having only one group containing active hydrogen
    • C08G18/2815—Monohydroxy compounds
    • C08G18/282—Alkanols, cycloalkanols or arylalkanols including terpenealcohols
    • 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
    • C08G18/71—Monoisocyanates or monoisothiocyanates
    • C08G18/718—Monoisocyanates or monoisothiocyanates containing silicon
    • 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 present invention relates to polyoxysilane-modified polyurethanes and their use as binders for sealants.
  • Alkoxysilane-functional polyurethanes which crosslink via a silane polycondensation have long been known. A review on this topic can be found eg in "Adhesives Age” 4/1995, page 30 ff. (Authors: Ta-Min Feng, BA Waldmann). Such alkoxysilane-terminated, moisture-curing, one-component polyurethanes are increasingly being used as soft-elastic coating, sealing and adhesive compounds in construction and in the automotive industry. Preparation processes for such alkoxysilane-functional polyurethanes are described in various publications, inter alia in US Pat. No. 3,627,722 or US Pat. No. 3,632,557.
  • a disadvantage of these methods is the high resulting viscosity, which requires the use of solvents or, at low viscosity, the poor suitability for use in low-modulus sealants.
  • various approaches are described, for example, in US Pat. No. 3,627,722 and EP-A 0 596 360, all of which have the disadvantage that in the preparation of the alkoxysilane-functional polyurethanes, intermediates are passed through which are very unstable and thus pose a high safety risk and severely limit the reproducibility of the reactions.
  • prepolymers having the required properties can be prepared by reacting polyethers having a number-average molecular weight of> 20,000 g / mol with OH-reactive silane building blocks.
  • the invention therefore relates to polyurethanes modified with alkoxysilane groups, which are obtainable by reacting the components A and B in the sense of a urethanization:
  • X, Y, Z are independently linear, cyclic or branched Ci-Cg-alkyl or Ci-C 8 alkoxy, wherein at least one of Radicals is a C 1 -C 8 -alkoxy group and X, Y or Z can also be bridged independently of one another,
  • R is any at least difunctional organic radical, preferably a straight-chain, branched or cyclic Alkylenradical having 1 to 8 carbon atoms.
  • X, Y, and Z in formula (I) are independently methoxy or ethoxy.
  • radical R a methylene or propylene radical is particularly preferred.
  • component A) has a number average molecular weight of 21,000 g / mol to 25,000 g / mol.
  • the invention further provides sealants based on the alkoxysilane-modified polyurethanes according to the invention which have a modulus at 100% elongation of not more than 0.4 N / mm 2 (according to ISO 11600) and a maximum of 30% by weight of plasticizer, preferably at most Contain 25 wt .-% plasticizer, more preferably at most 20 wt .-% plasticizer.
  • Polyol component A) which can be used according to the invention are the polyether polyols customary in polyurethane chemistry. These are accessible in a manner known per se by alkoxylation of suitable starter molecules with base catalysis or use of double metal cyanide compounds (DMC compounds).
  • suitable starter molecules for the preparation of polyether polyols are molecules having at least 2 element-hydrogen bonds which are reactive toward epoxides or any mixtures of such starter molecules.
  • Suitable starter molecules for the preparation of polyether polyols are, for example, simple, low molecular weight polyols, water, ethylene glycol, propanediol 1, 2, 2,2-bis (4-hydroxyphenyl) propane, Propylene glycol-1,3- and 1,4-butanediol, 1,6-hexanediol, neopentyl glycol, 2-ethylhexanediol-1, 3, trimethylolpropane, glycerol, pentaerythritol, sorbitol, organic polyamines having at least two NH bonds such as triethanolamine, ammonia , Methylamine or ethylenediamine or any mixtures of such starter molecules.
  • Alkylene oxide suitable for the alkoxylation is in particular propylene oxide.
  • propylene oxide polyethers having from 1.5 to 3.5 hydroxyl groups, more preferably from 1.8 to 2.5.
  • Polyethers prepared by double metal cyanide catalysis generally have a particularly low content of unsaturated end groups of less than or equal to 0.02 meq / gram of polyol (meq / g), preferably less than or equal to 0.015 meq / g, more preferably less than or equal to 0, 01 meq / g (method of determination ASTM D2849-69), contain significantly fewer monols and usually have a low polydispersity of less than 1.5.
  • polyethers prepared by double metal cyanide catalysis.
  • Particularly preferred are polyethers which have a polydispersity of 1.0-1.5; most preferably a polydispersity of 1.0 to 1.3.
  • Such polyethers are e.g. in US Pat. No. 5,158,922 and EP-A 0 654 302.
  • polyoxyalkylene polyols can be used in pure form or as a mixture of different polyethers.
  • isocyanate- and alkoxysilane-containing compounds B all alkoxysilane-containing monoisocyanates are suitable in principle.
  • Examples of such compounds are isocyanatomethyltrimethoxysilane, isocyanatomethyltriethoxysilane, (isocyanatomethyl) methyldimethoxysilane, (isocyanatomethyl) methyldiethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-isocyanatopropylmethyldimethoxysilane, 3-isocyanato propyltriethoxysilane and 3-isocyanatopropylmethyldiethoxysilane.
  • Preferred here is the use of 3-isocyanatopropyltrimethoxysilane.
  • isocyanate-functional silanes prepared by reacting a diisocyanate with an amino or thiosilane, as described in US Pat. No. 4,146,585 or EP-A 1 136 495.
  • the urethanization of components A) and B) may optionally be carried out using a catalyst.
  • Suitable catalytically active compounds which are known to the person skilled in the art are known urethanization catalysts such as organotin compounds or amine catalysts.
  • organotin compounds are: dibutyltin diacetate, dibutyltin dilaurate, dibutyltin bis-acetoacetonate and tin carboxylates such as, for example, tin octoate.
  • the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
  • Dibutyltin dilaurate is particularly preferably used as the urethanization catalyst.
  • the course of the urethanization reaction can be monitored by suitable measuring devices installed in the reaction vessel and / or by analyzes on samples taken. Suitable methods are known to the person skilled in the art. These are, for example, viscosity measurements, measurements of the NCO content, the refractive index, the OH content, gas chromatography (GC), nuclear magnetic resonance spectroscopy (NMR), infrared spectroscopy (IR) and near near-infrared spectroscopy (NIR).
  • the NCO content of the mixture is determined titrimetrically.
  • the urethanization of components A) and B) is continued until a complete conversion of the OH groups of the compounds of component A) is reached.
  • the first possibility involves the addition of a further NCO-reactive component, which in a subsequent Reaction step is reacted with the remaining NCO groups.
  • a further NCO-reactive component which in a subsequent Reaction step is reacted with the remaining NCO groups.
  • These may be, for example, low molecular weight alcohols.
  • the second possibility for the further reduction of the NCO content of the reaction product of components A) and B) is an allophanatization reaction.
  • the remaining NCO groups are reacted with the previously formed urethane groups, preferably by adding a catalyst which promotes allophanatization.
  • the alkoxysilane-group-modified polyurethanes of the invention generally have a viscosity of less than 200,000 mPas, preferably less than 100,000 mPas, in each case measured at 23 ° C.
  • the compounds according to the invention are very suitable as binders for the preparation of low-modulus elastic sealants, preferably for vehicle construction and construction. These adhesives crosslink under the action of atmospheric moisture via a silanol polycondensation.
  • the polymers obtained by this crosslinking are also an object of the present invention, their chemical and physical properties are responsible for the outstanding quality of the seals produced.
  • the polyurethanes of the invention modified with alkoxysilane groups may be used together with the customary fillers, pigments, plasticizers, drying agents, additives, light stabilizers, antioxidants, thixotropic agents, catalysts, adhesion promoters and optionally other auxiliaries and additives are formulated by known methods of sealant production.
  • Suitable basic fillers used are precipitated or ground chalks, metal oxides, sulfates, silicates, hydroxides, carbonates and bicarbonates. Further fillers are e.g. reinforcing and non-reinforcing fillers such as carbon black, precipitated silicas, fumed silicas, quartz powder or various fibers. Both the basic fillers and the further reinforcing or non-reinforcing fillers may optionally be surface-modified. Particular preference is given to using as basic fillers precipitated or ground chalks and pyrogenic silicic acids. Mixtures of fillers can also be used.
  • plasticizers examples include phthalic acid esters, adipic acid esters, alkylsulfonic acid esters of phenol or phosphoric acid esters. Long-chain hydrocarbons, polyethers and vegetable oils can also be used as plasticizers. Due to the special properties of the polymer according to the invention, the proportion of plasticizer in the sealant formulation can be limited to ⁇ 30% by weight, preferably to ⁇ 25% by weight, particularly preferably to ⁇ 20% by weight.
  • thixotropic agents which may be mentioned are pyrogenic silicic acids, polyamides, hydrogenated castor oil derived products or else polyvinyl chloride.
  • suitable catalysts for curing it is possible to use all organometallic compounds and amine catalysts which, as is known, promote silane polycondensation.
  • Particularly suitable organometallic compounds are especially compounds of tin and titanium.
  • Preferred tin compounds are, for example: dibutyltin diacetate, dibutyltin dilaurate, dioctyltin methyl acetate and tin carboxylates such as stannous octoate or dibutyltin-bis-acetoacetonate.
  • the said tin catalysts may optionally be used in combination with amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
  • amine catalysts such as aminosilanes or 1,4-diazabicyclo [2.2.2] octane.
  • Preferred titanium compounds are, for example, alkyl titanates, such as diisobutyl-bisacetoacetic acid ethyl ester titanate.
  • amine catalysts are particularly suitable those having a particularly high base strength, such as amines with amidine structure.
  • Preferred amine catalysts are therefore, for example, l, 8-diazabicyclo [5.4.0] undec-7-ene or 1, 5-diazabicyclo [4.3.0] non-5-ene.
  • drying agents include alkoxysilyl compounds such as vinyl trimethoxysilane, methyltrimethoxysilane, z '-Butyltrimethoxysilan, Hexadecyltrimeth- oxysilane.
  • Adhesion promoters used are the known functional silanes, such as, for example, amino silanes, epoxysilanes and / or mercaptosilanes or mixtures of functional silanes.
  • the viscosity measurements were carried out according to ISO / DIS 3219: 1990 at a constant temperature of 23 ° C. and a constant shear rate of 250 / sec using a Physica MCR disk-viscous rotational viscometer (Anton Paar Germany GmbH, Ostfildern, DE) of the measuring cone CP 25-1 (25mm diameter, 1 ° cone angle).
  • RT The ambient temperature of 23 ° C prevailing at the time of the experiment.
  • Example 1 (according to the invention):
  • 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 24 hours over a distance of 35 cm.
  • the Drying Recorder is located in a climate room at 23 ° C and 50% rel. Humidity.
  • the skin-forming time is the time at which the permanent trace of the needle disappears from the film.
  • the binder with filler Socal ® UiS 2
  • plasticizer DINP Jayfiex TM
  • desiccant Desiccant
  • the adhesion promoter (Dynasylan ® 1146) is added and stirred in within 5 min at 1000 U / min.
  • the catalyst (Lupragen ® N700) is stirred at 1000 U / min and, finally, the finished mixture in vacuo tet deaerated.
  • the level of plasticizer was classified below 20% by weight:
  • the sealant obtained with this low-softening formulation exhibits the following mechanical properties:

Abstract

La présente invention concerne des prépolymères contenant des groupes alcoxysilane ainsi que leur utilisation comme liants pour produits d'étanchéité.
PCT/EP2010/068952 2009-12-09 2010-12-06 Produits d'étanchéité WO2011069954A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
CN2010800562013A CN102741308A (zh) 2009-12-09 2010-12-06 密封剂
US13/514,742 US8981030B2 (en) 2009-12-09 2010-12-06 Sealants
EP10790748A EP2510029A1 (fr) 2009-12-09 2010-12-06 Produits d'étanchéité
JP2012542488A JP2013513674A (ja) 2009-12-09 2010-12-06 シーラント

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102009057599.5 2009-12-09
DE200910057599 DE102009057599A1 (de) 2009-12-09 2009-12-09 Dichtstoffe

Publications (1)

Publication Number Publication Date
WO2011069954A1 true WO2011069954A1 (fr) 2011-06-16

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Application Number Title Priority Date Filing Date
PCT/EP2010/068952 WO2011069954A1 (fr) 2009-12-09 2010-12-06 Produits d'étanchéité

Country Status (6)

Country Link
US (1) US8981030B2 (fr)
EP (1) EP2510029A1 (fr)
JP (1) JP2013513674A (fr)
CN (1) CN102741308A (fr)
DE (1) DE102009057599A1 (fr)
WO (1) WO2011069954A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102014101949A1 (de) * 2014-02-17 2015-08-20 Franken Systems Gmbh Verfahren zur druckwasserfesten Abdichtung von Bauwerken
US20160244549A1 (en) * 2015-02-25 2016-08-25 Bayer Materialscience Llc Alkoxysilane-group modified polyurethanes and low modulus sealants formed therefrom
KR101901020B1 (ko) * 2016-10-25 2018-11-08 한국타이어 주식회사 공명음 저감 타이어
DE102020117919A1 (de) * 2020-07-07 2022-01-13 Franken Systems Gmbh 2-Komponenten-Beschichtungszusammensetzung zur Bauwerksabdichtung

Citations (11)

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Publication number Priority date Publication date Assignee Title
US3627722A (en) 1970-05-28 1971-12-14 Minnesota Mining & Mfg Polyurethane sealant containing trialkyloxysilane end groups
US3632557A (en) 1967-03-16 1972-01-04 Union Carbide Corp Vulcanizable silicon terminated polyurethane polymers
US4146585A (en) 1977-03-02 1979-03-27 Union Carbide Corporation Process for preparing silane grafted polymers
US5158922A (en) 1992-02-04 1992-10-27 Arco Chemical Technology, L.P. Process for preparing metal cyanide complex catalyst
EP0596360A1 (fr) 1992-11-06 1994-05-11 Bayer Ag Composés d'alcoxysilanes contenant des groupes amino
EP0654302A1 (fr) 1993-11-23 1995-05-24 ARCO Chemical Technology, L.P. Catalyseur amélioré à base de complexe de cyanure métallique double
EP1136495A2 (fr) 2000-03-18 2001-09-26 Degussa AG 1:1 Monoadducts d'aminoalkylalkoxysilanes et diisocyanates, leur préparation et utilisation
EP1591464A1 (fr) 2004-04-28 2005-11-02 Bayer MaterialScience LLC Polyéther-uréthanes réticulables sous humidité et leur utilisation comme agent d'étanchéité, adhésif et revêtement
WO2007025668A1 (fr) * 2005-09-03 2007-03-08 Bayer Materialscience Ag Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes
WO2008036364A1 (fr) * 2006-09-21 2008-03-27 Momentive Performance Materials Inc. Procédé de préparation d'une résine polyuréthanne silylé durcissable
WO2009071542A1 (fr) * 2007-12-04 2009-06-11 Henkel Ag & Co. Kgaa Compositions durcissables contenant des polyuréthannes silylés

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US6833423B2 (en) * 2002-06-18 2004-12-21 Bayer Polymers Llc Moisture-curable, polyether urethanes with reactive silane groups and their use as sealants, adhesives and coatings
JP4885540B2 (ja) * 2003-04-11 2012-02-29 株式会社カネカ 硬化性組成物
JPWO2009011329A1 (ja) * 2007-07-19 2010-09-24 株式会社カネカ 硬化性組成物
DE102007039648A1 (de) * 2007-08-22 2009-02-26 Sustech Gmbh & Co. Kg Mischungen, multifunktioneller sternförmiger Präpolymere, deren Herstellung und Verwendung sowie Beschichtungen daraus
WO2009072542A1 (fr) 2007-12-07 2009-06-11 Suntory Holdings Limited Plante transgénique capable de fleurir dans des conditions de faible intensité lumineuse

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Publication number Priority date Publication date Assignee Title
US3632557A (en) 1967-03-16 1972-01-04 Union Carbide Corp Vulcanizable silicon terminated polyurethane polymers
US3627722A (en) 1970-05-28 1971-12-14 Minnesota Mining & Mfg Polyurethane sealant containing trialkyloxysilane end groups
US4146585A (en) 1977-03-02 1979-03-27 Union Carbide Corporation Process for preparing silane grafted polymers
US5158922A (en) 1992-02-04 1992-10-27 Arco Chemical Technology, L.P. Process for preparing metal cyanide complex catalyst
EP0596360A1 (fr) 1992-11-06 1994-05-11 Bayer Ag Composés d'alcoxysilanes contenant des groupes amino
EP0654302A1 (fr) 1993-11-23 1995-05-24 ARCO Chemical Technology, L.P. Catalyseur amélioré à base de complexe de cyanure métallique double
EP1136495A2 (fr) 2000-03-18 2001-09-26 Degussa AG 1:1 Monoadducts d'aminoalkylalkoxysilanes et diisocyanates, leur préparation et utilisation
EP1591464A1 (fr) 2004-04-28 2005-11-02 Bayer MaterialScience LLC Polyéther-uréthanes réticulables sous humidité et leur utilisation comme agent d'étanchéité, adhésif et revêtement
WO2007025668A1 (fr) * 2005-09-03 2007-03-08 Bayer Materialscience Ag Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes
EP1924621A1 (fr) 2005-09-03 2008-05-28 Bayer MaterialScience AG Prepolymeres contenant des groupes alcoxysilane de faible viscosite, procede de production et utilisation associes
WO2008036364A1 (fr) * 2006-09-21 2008-03-27 Momentive Performance Materials Inc. Procédé de préparation d'une résine polyuréthanne silylé durcissable
WO2009071542A1 (fr) * 2007-12-04 2009-06-11 Henkel Ag & Co. Kgaa Compositions durcissables contenant des polyuréthannes silylés

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Title
ADHESIVES AGE, April 1995 (1995-04-01), pages 30
See also references of EP2510029A1 *

Also Published As

Publication number Publication date
CN102741308A (zh) 2012-10-17
US20120245279A1 (en) 2012-09-27
EP2510029A1 (fr) 2012-10-17
US8981030B2 (en) 2015-03-17
DE102009057599A1 (de) 2011-06-16
JP2013513674A (ja) 2013-04-22

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