WO2001083577A2 - Procede de production d'elastomere polyurethane - Google Patents

Procede de production d'elastomere polyurethane Download PDF

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Publication number
WO2001083577A2
WO2001083577A2 PCT/US2001/013985 US0113985W WO0183577A2 WO 2001083577 A2 WO2001083577 A2 WO 2001083577A2 US 0113985 W US0113985 W US 0113985W WO 0183577 A2 WO0183577 A2 WO 0183577A2
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WO
WIPO (PCT)
Prior art keywords
percent
weight
composition
polyisocyanate
polyol
Prior art date
Application number
PCT/US2001/013985
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English (en)
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WO2001083577A3 (fr
Inventor
Luigi Pellacani
Michael Janssen
Holger Paschke
Klaus Haase
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Dow Global Technologies Inc.
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 Dow Global Technologies Inc. filed Critical Dow Global Technologies Inc.
Priority to US10/258,418 priority Critical patent/US20030212236A1/en
Priority to EP01932803A priority patent/EP1320562A2/fr
Priority to MXPA02010800A priority patent/MXPA02010800A/es
Priority to BR0110672-4A priority patent/BR0110672A/pt
Publication of WO2001083577A2 publication Critical patent/WO2001083577A2/fr
Publication of WO2001083577A3 publication Critical patent/WO2001083577A3/fr

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    • 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
    • C08G18/20—Heterocyclic amines; Salts thereof
    • C08G18/2045—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings
    • C08G18/2063—Heterocyclic amines; Salts thereof containing condensed heterocyclic rings having two nitrogen atoms in the condensed ring system
    • 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

Definitions

  • the present invention relates to a process for producing elastomers using prepolymers based on aromatic diisocyanates and containing a low level of unreacted toluene diisocyanate (TDI) .
  • TDI toluene diisocyanate
  • TDI isocyanate component of the prepolymer.
  • Commercially available TDI generally consists of an 80:20 blend of two isomers, the 2,4-TDI and the 2,6-TDI isomer.
  • the 2,4-TDI isomer carries one isocyanate (NCO) group in the para position versus the methyl group, and one NCO group in the ortho position versus the methyl group.
  • the NCO in the para position has greater reactivity in forming a urethane bond.
  • a prepolymer When reacting commercially available TDI with a polyol to form a prepolymer, a prepolymer is produced which generally contains a majority of isocyanate groups in the ortho position versus the methyl group. These prepolymers are thus less reactive than the polyisocyanate monomers in subsequent reactions with the curative components for producing polyurethane products. Due to the low reactivity of such prepolymers, the prepolymers are generally manufactured by reaction of the polyol with a stoichiometric excess of polyisocyanate monomer, and therefore contain sufficient free polyisocyanate monomers that the reaction rates in polyurethane formation are acceptable.
  • U.S. Patent 4,556,703 discloses the preparation of polyurethane elastomers using TDI feed systems high in 2, 6-isomer content for the preparation of the prepolymer. After prepolymer formation, the excess (unreacted) TDI is removed. The higher concentrations of 2,6-isomer is reported to give elastomers having lower heat buildup on flexing.
  • U.S. Patent 4,556,703 discloses the preparation of polyurethane elastomers using TDI feed systems high in 2, 6-isomer content for the preparation of the prepolymer. After prepolymer formation, the excess (unreacted) TDI is removed. The higher concentrations of 2,6-isomer is reported to give elastomers having lower heat buildup on flexing.
  • Patents 4,507,459 and 4,519,432 describe the synthesis of polyurethanes having low hysteresis, by reacting a prepolymer of a mononuclear aromatic diisocyanate and polyol with a chain extender mixture of mononuclear aromatic diamine and polyol.
  • U.S. Patents 4,507,459 and 4,519,432 describe the synthesis of polyurethanes having low hysteresis, by reacting a prepolymer of a mononuclear aromatic diisocyanate and polyol with a chain extender mixture of mononuclear aromatic diamine and polyol.
  • 5,115,071 describes polyurethane coatings formed from prepolymers made by reacting polyisocyanates with long chain polyols and then removing the excess unreacted polyisocyanate from the prepolymer.
  • the resulting prepolymers are chain extended with compounds having active hydrogen atoms. None of the above systems solves the problem of the poor reaction rate between prepolymers based on TDI that have a low level of free TDI monomer and hydroxyl terminated curatives, particularly when operating at temperatures close to room temperature.
  • EP Patent 154180 describes the use of certain synergistic catalyst compositions for the formation of polyurethanes by reaction between hydroxyl-containing compounds and certain tertiary aliphatic diisocyanates .
  • the reported synergistic catalyst compositions includes 1, 8-diazabicyclo (5.4.0) -undec-7-ene (DBU) .
  • DBU 1, 8-diazabicyclo
  • U.S. Patent 4,150,206 describes a process for preparing foamed polyurethane with integral skin, by reacting in a mold, a polyol, a polyisocyanate, at most one part by weight of water to 100 parts by weight of polyol and catalyst, wherein the improvement comprises using an aliphatic polyisocyanate and a synergistic catalyst combination that includes DBU.
  • DE Patent 1745418 describes a process for producing polyurethane resins from conventional polyisocyanates wherein the catalyst mixtures includes DBU. While disclosing the use of DBU, these patents make no reference to the usefulness of DBU as catalyst when reacting prepolymers based only or mainly on TDI that have a low level of free TDI monomer with curative components containing only or mainly hydroxyl-containing compounds.
  • the present invention is to an elastomeric composition prepared by mixing (a) a polyisocyanate, (b) a curative component and (c) a catalyst consisting essentially of 1, 8-diazabicyclo (5, 4, 0) undec-7-ene at an isocyanate index from 75 to 140; wherein at least 70 percent by weight of the polyisocyanate is a toluene diisocyanate terminated prepolymer containing less than about 2 percent by weight free toluene diisocyanate monomer and the curative component contains compounds having isocyanate-reactive groups, wherein at least 40 percent by weight of the compounds having isocyanate-reactive groups are compounds having at least one hydroxyl group.
  • compositions unexpectedly provide rapid curing.
  • DBU inherently slow reacting polyisocyanate
  • the usage of DBU allows one to achieve complete cure in an acceptable time, even when operating at close to room temperature, and in the absence of traditional strong catalysts for the urethane bond formation, such as tin or lead catalysts.
  • the possibility to reduce or eliminate the use of tin and lead catalysts further increases the low hazard profile associated with the present inventive formulation technology.
  • the polyurethane elastomers prepared according to the teachings of the present invention are characterized by better tear- tensile-elongation properties, which reflects more complete curing due to the use of the DBU catalyst.
  • an elastomeric composition is provided by the present invention using prepolymers derived from TDI. It has been unexpectedly found that fast curing rates for urethane polymers can be achieved when using TDI prepolymers having a low free TDI monomer content by using a catalyst consisting essentially of 1,8- diazabicyclo (5, 4 , 0) undec-7-ene (DBU) .
  • DBU 1,8- diazabicyclo
  • the polyisocyanate composition contains at least 70 percent by weight of a TDI terminated prepolymer containing less than about 2 percent by weight free toluene diisocyanate monomer.
  • TDI TDI terminated prepolymer
  • Crude toluene diisocyanate obtained by the phosgenation of a mixture of toluene diamine can also be used in the present invention.
  • prepolymers are well known in the art. Generally, the prepolymer is formed by condensation polymerization of a stoichiometric excess of polyisocyanate with a polyol .
  • Suitable polyols include those described in U.S. Patent 4,456,642, the disclosure of which is incorporated by reference. Suitable polyols are represented by polyether polyols, polyester polyols, polycarbonate polyols and polyacetal polyols. Polyamino- or polymercapto-containing compounds can also be included.
  • Suitable polyether polyols include those prepared by polymerizing an alkylene oxide in the presence of a two to eight functional initiator compound.
  • initiators examples include water, alcohols, diols, ammonia, amines, and polyfunctional hydroxylated initiators such as glycerine, sorbitol, sucrose.
  • polyether polyols include polyethyleneoxy polyols, polypropyleneoxy polyols, polybutyleneoxy polyols, and block copoly ers of ethylene oxide and propylene oxide.
  • the polyether polyol is a polypropyleneoxy polyol, or a block copolymer of ethylene oxide and propylene oxide, or a mix- feed copolymer of ethylene oxide and propylene oxide.
  • Suitable exemplary polyols include Voranol P 400, Voranol P 2000, Voranol EP 1900, Voranol CP 4755, and Voranol HF 505 available from The Dow Chemical Company.
  • Suitable polyether polyols also include polytetramethylene glycols.
  • Suitable polyester polyols include polyesters formed from a glycol and a saturated polyfunctional dicarboxylic acid such as prepared by reacting monoethylene glycol with adipic acid.
  • Suitable polyester polyols with improved hydrolytic stability include polyesters formed from a glycol and a saturated polyfunctional dicarboxylic acid such as prepared by reacting hexanediol with dodecanoic acid. Also polyester of lactones can be employed for the purposes of the present invention. Polyhydroxy compounds corresponding to naturally occurring polyols
  • polyhydroxy compounds modified by vinyl polymers which are obtained by the polymerization of styrene and acrylonitrile in the presence of polyether polyols, are suitable for the present invention.
  • Polyhydroxy compounds in which high molecular weight polyadducts or polycondensates are contained in a finely dispersed or dissolved form may also be employed in the present invention.
  • the TDI prepolymers used in the present invention contain less than 2 percent by weight of free (unreacted) TDI monomer. Preferably the prepolymers contain less than 1 percent by weight of TDI free monomer. More preferably the prepolymers contain less than 0.5 percent by weight of free TDI monomer. In a most preferred embodiment, the prepolymer contains less than 0.1 percent by weight of free TDI monomer.
  • Such methods include reacting a polyol with an excess of TDI followed by distillation to remove the excess TDI from the formed prepolymer.
  • Another common method is to add TDI to a polyol at close to stoichiometric ratios of isocyanate groups to hydroxyl group, for example, from about 1.2 to less than 2 isocyanate groups per hydroxyl group.
  • Further industrial methods for the manufacturing of prepolymers with low free TDI content include solvent extraction of the unreacted TDI, and selective adsorption of the unreacted TDI. Any of the industrial methods for the manufacturing of prepolymers with low free TDI content may be used for the purposes of the present invention.
  • the polyisocyanate composition of the present invention generally contains at least 70 percent by weight of a TDI prepolymer. In a preferred embodiment, the polyisocyanate composition contains at least 75 percent by weight of a TDI prepolymer. In a more preferred embodiment the polyisocyanate is at least 80 percent by weight of a TDI prepolymer. In a most preferred embodiment the polyisocyanate is at least 85 percent by weight of a TDI prepolymer.
  • the polyisocyanate component can contain other known aromatic and aliphatic isocyanates .
  • additional polyisocyanate components can be added to modify the properties of the TDI prepolymers, for instance to reduce its viscosity. They may also be added to modify the properties of the final elastomer.
  • aromatic polyisocyanates polymethylene polyphenylene isocyanates, the 2,2', 2,4' and 4,4' iso ers of diphenylmethylene diisocyanate, their carbodiimide modified version, and mixtures thereof are preferred.
  • aromatic polyisocyanates examples include m- and p-phenylenediisocyanate, chlorophenylene-2 , 4-diisocyanate, diphenylene-4 , 4 ' -diisocyanate, 4,4'- diisocyanate-3, 3 ' -dimehtyldiphenyl , 3-methyldiphenyl-methane-4, 4 ' - diisocyanate and diphenyletherdiisocyanate and 2,4,6- triisocyanatotoluene and 2, 4, 4 ' -triisocyanatodiphenylether .
  • aliphatic polyisocyanates which can be used with the TDI prepolymers of the present invention include, 1, 6-hexamethylene diisocyanate (HDI) , 3-isocyanatomethyl-3 , 5, 5- trimethylcyclohexylisocyanate (IPDI) , m-tetramethylenexylene diisocyanate (TMXDI) , and bis (4-isocyanateocyclohexyl) methane and bis (4-isocyanateocyclohexyl) .
  • HDI 1, 6-hexamethylene diisocyanate
  • IPDI 3-isocyanatomethyl-3
  • IPDI 5- trimethylcyclohexylisocyanate
  • TXDI m-tetramethylenexylene diisocyanate
  • bis (4-isocyanateocyclohexyl) methane and bis (4-isocyanateocyclohexyl) bis
  • aliphatic isocyanates are preferably used in one of the various commercially available modified versions, characterized by low free aliphatic isocyanate monomer content, like the isocyanurate or the biuret .
  • Hindered aliphatic isocyanates as disclosed in U.S. Patents 4,547,478 and 4,598,103, the disclosures of which are incorporated by reference, may be also be used in the present inventions with the TDI prepolymers.
  • Further examples of aromatic isocyanates and their derivatives are listed in U.S. Patent 4,456,642, the disclosures of which is incorporated by reference.
  • the curative component contains isocyanate-reactive compounds, with at least 40 percent by weight of the compounds having isocyanate- reactive groups consisting of compound having at least one hydroxyl groups. In a preferred embodiment, at least 50 percent by weight of the isocyanate-reactive compounds are compounds having at least one hydroxyl group .
  • the hydroxyl-carrying compound used in the curative in producing the elastomers of the present invention include (a) any of the polyols as disclosed above for producing the prepolymer and (b) chain extenders or cross-linkers.
  • the polyol has a functionality of 2 to 8 and a hydroxyl equivalent weight between 301 and 2000. Hydroxyl-carrying compounds having lower equivalent weight will act as chain extenders or as crosslinking agents.
  • the ratio between high molecular weight and low molecular weight hydroxyl- carrying compound used in the curative in producing the elastomers of the present invention may be adjusted depending on the desired physical -mechanical properties of the final elastomer.
  • Cross-linkers include alkanolamines and other compounds of 300 or lower equivalent weight having from 3 to 8 , preferably from 3 to 4 , active hydrogen containing groups per molecule .
  • Examples of such compounds include glycerine and trimethyolpropane, as well as other alkylene oxide triols .
  • alkanolamines such as diethanolamine, triisopropanolamine, triethanolamine, diisopropanolamine, adducts of 4-8 moles of ethylene oxide and/or propylene oxide with ethylene diamine, and ammonia.
  • the cross-linkers will create a three-dimensional polymer network. Increased stiffness and rigidity can be accomplished through use of cross-linkers .
  • Chain extenders include compounds having two active hydrogen- containing groups per molecule and an equivalent weight of from 30 to 300, preferably from 30 to 150.
  • chain extenders include low-molecular polyhydric alcohols such as ethylene glycol, diethylene glycol, 1, 3 -propylene glycol, 1, 4-butanediol , 1, 6-hexamethylene glycol, diethylene glycol, triethylene glycol, and dipropylene glycol.
  • Suitable chain extenders for the purpose of the present invention also include polyamines such as ethylene diamine, xlylenediamine, methylene-bis (o-chloroaniline, and diethyl toluene diamine. Chain extenders, when reacted with the isocyanates, will result in increased hard segment density within the matrix of the cured polyurethane polymer. Hard segments result in high-temperature properties and higher rigidity (hardness) of the polymer.
  • crosslinking agents or chain extenders are known in the art as disclosed in U.S. Patents 4,863,979 and 4,963,399 and EP 549,120, the disclosures of which are incorporated herein by reference .
  • the isocyanate index defined as the number or equivalents of NCO groups divided by the total number of isocyanate reactive hydrogen atom equivalents multiplied by 100, ranges from 75 to 140, and preferably from 85 to 120.
  • the amount of DBU catalyst used is from about 0.005 to 2 percent by weight, and preferably from 0.01 to 1.0 percent by weight based on total polyol plus isocyanate.
  • the catalyst is commercially available as Polycat DBU from Air Products, as PC Cat DBU from Nitroil and as DBU from BASF. Additional catalysts may be used in combination with the DBU.
  • Such catalysts include tertiary amine catalysts, such as triethylene diamine, and organic tin compounds such as tin acetate, tin octanoate, tin oleate, tin laurate and dialkyl tin decarboxylates .
  • tertiary amine catalysts such as triethylene diamine
  • organic tin compounds such as tin acetate, tin octanoate, tin oleate, tin laurate and dialkyl tin decarboxylates .
  • fillers and other conventional additives such as pigments, cross-linkers, chain extenders, defoaming agents, plasticizers, etc.
  • Suitable plasticizers include esters of polybasic (preferably dibasic) carboxylic acids with monohydric alcohols.
  • Polymeric plasticizers such as polyesters of adipic acid, sebacic acid or phthalic acid can also be used.
  • Plasticizers Petroleum-based hydrocarbon distillates, phenol alkylsufonates and phenyl paraffin sulfonates are other examples of plasticizers . Further suitable plasticizers are those disclosed in U.S. Patent 4,456,642, the disclosures of which is incorporated herein by reference.
  • the Shore A hardness, as measured by DIN 53505, of the elastomers of the present invention are generally greater than 10. Preferably the Shore A hardness is greater than 15. More preferred are elastomers with a Shore A hardness of 20 or greater.
  • Elastomers produced according to the present invention have a wide variety of applications. Examples include shaped products subjected to severe mechanical stresses, such as tires, rollers and cone belts, wheels for industrial or for recreational goods, elastomer for footwear applications, tooling compounds.
  • the density of the elastomeric products are generally greater than 0.7 g/cm 3 , preferably greater than 0.8 g/cm 3 .
  • the elastomers of the present invention may be manufactured by casting, spraying or reaction injection molding.
  • the process of the present invention is particularly applicable for making elastomers when the reaction temperature is below 100°C and particularly from temperatures from 20 to 75°C.
  • Polyol A is a dipropyleneglycol inititated polyol having an hydroxyl equivalent weight of 2,000, available from The Dow Chemical Company.
  • Polyol B is a sorbitol initiated polyoxyethylene/ polyoxypropylene polyether polyol (approximately 20 percent EO cap) having an hydroxyl equivalent weight of about 2,000, available from The Dow Chemical Company.
  • Antifoaming agent the antifoaming agent was obtained from Byk AG.
  • DETDA is diethyltoluene diamine used as a chain extender.
  • Dabco 33 LV is an amine catalyst (33 percent triethylene diamine in dipropylene glycol) available from Air Products .
  • Dabco T-12 is dibutyl tin dilaurate obtained from Air Products .
  • DBU is 1, 8-diazabicyclo (5, 4 , 0) undec-7-ene obtained from Air Products .
  • Isocyanate A is a TDI prepolymer with low free TDI content ( ⁇ 0.5 percent) obtained from TDI and a polyether polyol : the NCO content is about 3.5 percent, available from The Dow Chemical Company under the Tradename VORASTAR B 1503.
  • Isocyanate B is a TDI prepolymer with low free TDI content ( ⁇ 0.5 percent) obtained from TDI and a polyether polyol: the NCO content is about 2.0 percent .
  • the pre-mixed formulated polyol component is added in a plastic cup to the proper amount of isocyanate component, as per desired isocyanate index, followed by intensive mixing for 30 seconds, and followed by degassing.
  • the temperature of the components was about 40°C.
  • the reaction profile was monitored, measuring the potlife, which is the time at which the mixed material shows such a viscosity that it is no longer easily workable.
  • the mixture is poured in an open flat metal cup, thus preparing elastomer disks. No post-curing was applied. About 2 days after casting, the hardness of the disks was measured according to DIN 53505.
  • Example 1 shows that even though the catalyst level for Example 1 is much lower than the comparatives Examples A and B, the potlife is much shorter for Example 1 due to the use of the DBU. Furthermore, the use of DBU results in an improved balance of tear and tensile properties, which is an indication of a more complete curing reaction.

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

Abstract

Composition qui permet de produire un élastomère à l'aide de prépolymères à base de diisocyanate de toluène. Ladite composition est préparée par mélange (a) d'un polyisocyanate, (b) d'un composé de réticulation et (c) d'un catalyseur constitué essentiellement de 1,8-diazabicyclo(5,4,0)undéc-7-ène. Le polyisocyanate, qui constitue au moins 70 % en poids de la composition contenant de l'isocyanate, est un prépolymère à terminaison diisocyanate de toluène contenant moins d'environ 2 % en poids de monomère de diisocyanate de toluène libre, et le composé de réticulation contient des composés possédant des groupes réactifs à l'isocyanate, au moins 40 % en poids des composés possédant des groupes réactifs à l'isocyanate étant des composés pourvus d'au moins un groupe hydroxyle.
PCT/US2001/013985 2000-05-03 2001-05-01 Procede de production d'elastomere polyurethane WO2001083577A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
US10/258,418 US20030212236A1 (en) 2001-05-01 2001-05-01 Process for producing polyurethane elastomer
EP01932803A EP1320562A2 (fr) 2000-05-03 2001-05-01 Procede de production d'elastomere polyurethane
MXPA02010800A MXPA02010800A (es) 2000-05-03 2001-05-01 Proceso para producir elastomero de poliuretano.
BR0110672-4A BR0110672A (pt) 2000-05-03 2001-05-01 Composição e processo para produzir elastÈmero de poliuretano

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US20150600P 2000-05-03 2000-05-03
US60/201,506 2000-05-03

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WO2001083577A2 true WO2001083577A2 (fr) 2001-11-08
WO2001083577A3 WO2001083577A3 (fr) 2002-06-06

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EP (1) EP1320562A2 (fr)
CN (1) CN1430633A (fr)
BR (1) BR0110672A (fr)
MX (1) MXPA02010800A (fr)
WO (1) WO2001083577A2 (fr)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20050143478A1 (en) * 2003-12-24 2005-06-30 Kao Corporation Catalyst for preparing polyurethane
US20140342110A1 (en) * 2013-05-15 2014-11-20 Chemtura Corporation Thermoplastic Polyurethane From Low Free Monomer Prepolymer

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4124573A (en) * 1976-03-16 1978-11-07 Bridgestone Tire Co., Ltd. Soft polyurethane elastomer containing isocyanurate ring
US4952659A (en) * 1987-03-25 1990-08-28 The B. F. Goodrich Company Catalyzed fast cure polyurethane sealant composition
DE19816570A1 (de) * 1998-04-15 1999-10-21 Bayer Ag Reaktivsysteme und ihre Verwendung zur Herstellung von Beschichtungen, Klebstoffen, Dichtungsmassen, Vergußmassen oder Formteilen

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4124573A (en) * 1976-03-16 1978-11-07 Bridgestone Tire Co., Ltd. Soft polyurethane elastomer containing isocyanurate ring
US4952659A (en) * 1987-03-25 1990-08-28 The B. F. Goodrich Company Catalyzed fast cure polyurethane sealant composition
DE19816570A1 (de) * 1998-04-15 1999-10-21 Bayer Ag Reaktivsysteme und ihre Verwendung zur Herstellung von Beschichtungen, Klebstoffen, Dichtungsmassen, Vergußmassen oder Formteilen

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WO2001083577A3 (fr) 2002-06-06
BR0110672A (pt) 2003-04-29
CN1430633A (zh) 2003-07-16
EP1320562A2 (fr) 2003-06-25
MXPA02010800A (es) 2003-04-14

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