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WO2007110179A1 - Nouvelles compositions de polyol et utilisation de celles-ci - Google Patents

Nouvelles compositions de polyol et utilisation de celles-ci Download PDF

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Publication number
WO2007110179A1
WO2007110179A1 PCT/EP2007/002492 EP2007002492W WO2007110179A1 WO 2007110179 A1 WO2007110179 A1 WO 2007110179A1 EP 2007002492 W EP2007002492 W EP 2007002492W WO 2007110179 A1 WO2007110179 A1 WO 2007110179A1
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WIPO (PCT)
Prior art keywords
modified
organoclay
polyol
stable composition
polyols
Prior art date
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Ceased
Application number
PCT/EP2007/002492
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English (en)
Inventor
Carlos Fernandez-Llamazares Rodriguez
Josep GIMENO BOLAÑO
José Maria MONSO CAPELLADES
Jesús SANTAMARIA SERNA
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Synthesia Espanola SA
Original Assignee
Synthesia Espanola SA
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 Synthesia Espanola SA filed Critical Synthesia Espanola SA
Priority to EP07723450A priority Critical patent/EP1999202A1/fr
Publication of WO2007110179A1 publication Critical patent/WO2007110179A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • 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
    • 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
    • C08G71/00—Macromolecular compounds obtained by reactions forming a ureide or urethane link, otherwise, than from isocyanate radicals in the main chain of the macromolecule
    • C08G71/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/34—Silicon-containing compounds
    • C08K3/346—Clay
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C08K5/19—Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/49—Phosphorus-containing compounds
    • C08K5/51—Phosphorus bound to oxygen
    • C08K5/52—Phosphorus bound to oxygen only
    • C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
    • C08L71/02—Polyalkylene oxides

Definitions

  • the present invention relates to new polyol compositions and modified organoclays and to the use of said compositions as the polyol component of a polyurethane system.
  • the invention also relates to formulations for rigid and flexible polyurethane foams comprising the new polyol component.
  • Polyurethane foam is obtained by reacting a polyisocyanate compound with a polyol compound.
  • a polyol is a compound that comprises several hydroxy! groups in its molecular structure and the most commonly used in formulations of polyurethane foams tend to be polyethers and/or polyesters.
  • the reaction medium used to produce polyurethane is designed to include: flame retardants, catalysts of the polymerisation reaction between the polyisocyanate compound and the polyol compound (or gelling catalysts), catalysts of the reaction between the polyisocyanate compound and water (or foaming catalysts), silicone surfactants and physical foaming agents (e.g. HFC) and chemical foaming agents (water). All these elements that are present in the reaction medium tend to be mixed together with the polyol compound in which it is known as the polyol component or formulated polyol.
  • polyisocyanate component plus the polyol component is known as a polyurethane system.
  • additives such as modified organoclays have recently begun to be used, which, if correctly exfoliated in the polyurethane matrix, favour said improvements.
  • the organoclays used are clays modified by the intercalation of quaternary ammonium groups. They come from clays, i.e. from minerals consisting mainly of hydrated aluminosilicates whose structure includes cations and which are structured in many ways, e.g. in sheets.
  • clay or phyllosilicate is montmorillonite (MMT).
  • MMT montmorillonite
  • Na + and Ca 2+ cations that are situated between the layers of silicate in its original structure have been chemically substituted for quaternary ammonium compounds that enable expansion between the sheet layers of silicate.
  • the state of the art in the use of such materials in polyurethane foams has recently been described by X. Cao (Polymer 46,2005, 775-783) and L. James Lee (Composites Science and Technology 65,2005, 2344-2363).
  • compositions adapted for polyurethane foam systems containing organoclays modified by the intercalation of quaternary ammonium groups are also some patents in the state of the art that disclose compositions adapted for polyurethane foam systems containing organoclays modified by the intercalation of quaternary ammonium groups.
  • EP 1209189 discloses a rigid polyurethane foam composition, containing up to 10% organoclays modified by the intercalation of quaternary ammonium groups dispersed in a foaming agent selected from the hydrofluorocarbon (HFC), hydrochlorofluorocarbon (HCFC) and hydrocarbon group.
  • a foaming agent selected from the hydrofluorocarbon (HFC), hydrochlorofluorocarbon (HCFC) and hydrocarbon group.
  • HFC hydrofluorocarbon
  • HCFC hydrochlorofluorocarbon
  • the foaming agent is mixed with the polymer composition or its precursors, so that some of the components used to produce the foam contain up to 10% organoclay in relation to the total weight of the polymer.
  • the organoclay is dispersed in the foaming agent solution using an ultrasonic bath.
  • organoclay modified by the intercalation of quaternary ammonium groups is in the isocyanate component and in order to achieve a homogeneous dispersion they must also be subjected to sonication by ultrasound.
  • the organoclay is not stable in the isocyanate component, producing an increase in viscosity during storage. The use of sonication makes its application difficult on an industrial scale.
  • WO 2006/003421 explains a mixture to form polyurethane foams that consists of the necessary agents to form such foams together with particles of organoclays modified by the intercalation of quaternary ammonium groups and at least one coupling agent of the neoalkoxy titanate or neoalkoxy zirconate type, such as Lica 12.
  • the mixture also comprises a flame retardant agent, such as triethyl phosphate or tris(chloropropyl) phosphate.
  • a flame retardant agent such as triethyl phosphate or tris(chloropropyl) phosphate.
  • To produce the final mixture it must be stirred vigorously by mechanical stirring, assisted by the use of ultrasound. The use of ultrasound makes its application difficult on an industrial scale, in addition to the high cost of these coupling agents.
  • compositions disclosed in WO 03059817 are intended for producing elastomers, i.e. thermoplastic non-foamed materials, and they are not applicable to rigid foams that must be sprayed. Furthermore, it must be emphasised that the compositions disclosed in this patent present problems of stability, specifically, settling of the modified organoclay and they require a great deal of stirring to be mixed properly.
  • the modified organoclay must be mixed with the polyol component just before performing the reaction with the isocyanate component. This makes the system complex, complicating the preparation of the mixture that must finally react to produce the desired foam.
  • compositions that are the object of the present invention do not present the problems posed by the state of the art because they are stable compositions and they also make it possible to produce polyurethane foams with greatly improved properties.
  • compositions of organoclayss modified by the intercalation of quaternary ammonium groups in polyols that are the object of the invention are characterised in that they are surprisingly stable, i.e. they do not present the problems of the state of the art and they are also characterised in that they comprise at least one polyol compound, at least one organoclay or phyllosilicate modified by the intercalation of quaternary ammonium groups and at least one organic phosphate or phosphonate.
  • the weight percentage of modified organoclay is between 0.5% and 10%; and the weight percentage of organic phosphate or phosphonate is between 30% and 70%.
  • organoclays modified by the intercalation of quaternary ammonium compounds or groups used are preferably organoclays of the montmorillonite
  • MMT metal-organic quaternary ammonium
  • substituents of the nitrogen atom are hydrogenated fat, methyl, methyl and benzyl.
  • the stable composition according to the invention is characterised in that the polyol compound is independently chosen from a non-alkoxylated polyester, polyether or Mannich base.
  • the organic phosphate or phosphonate is independently chosen preferably from triethyl phosphate (TEP) and tris(2-b ⁇ toxyethyl) phosphate (TBEP).
  • Another object of the present invention is a polyol component for polyurethane foam systems, characterised in that it comprises a stable composition of organoclay in polyols, which is formulated with at least one polyol compound, at least one organoclay or phyllosilicate modified by the intercalation of quaternary ammonium groups and at least one organic phosphate or phosphonate.
  • the polyol component comprises a stable composition of organoclays in polyols that represents a weight percentage, in relation to the total polyol component, of 10% to 70%.
  • Said stable dispersion of organoclays in polyols contains between 30% and 70% by weight of polyol compound or compounds, between 0.5% and 10% by weight of organoclay and between 30% and 70% by weight of organic phosphate or phosphonate.
  • the organic phosphate in said polyol component is independently chosen from triethyl phosphate (TEP) or tris(2-butoxyethyl) phosphate (TBEP).
  • TEP triethyl phosphate
  • TBEP tris(2-butoxyethyl) phosphate
  • the composition of organoclays in polyols preferably comprises as the organoclay montmorillonite (MMT) modified by the intercalation of quaternary ammonium groups where the substituents of the nitrogen atom are hydrogenated fat, methyl, methyl and benzyl.
  • MMT organoclay montmorillonite
  • Another object of the present invention is a formulation for rigid polyurethane foams, characterised in that it comprises a polyisocyanate component and a polyol component, wherein said polyol component is a stable composition of modified organoclay in polyols, which is formulated with at least one polyol compound, at least one modified organoclay, also referred to as phyllosilicate, modified by the intercalation of quaternary ammonium groups, and at least one organic phosphate or phosphonate.
  • the polyol component of the formulation for rigid polyurethane foams comprises a stable composition of organoclays in polyols that represents a weight percentage, in relation to the total polyol component, of 10% to 70%.
  • Said stable dispersion of organoclays in polyots contains between 30% and 70% by weight of polyol compound or compounds, between 0.5% and 10% by weight of organoclay, and between 30% and 70% by weight of organic phosphate.
  • the formulation for rigid polyurethane foams is used for foams that must be applied by spraying.
  • Another object of the present invention is a formulation for flexible polyurethane foams, characterised in that it comprises a polyisocyanate component and a polyol component, wherein said polyol component is a stable composition of organoclay in polyols, which is formulated with at least one polyol compound, at least one organoclay, also referred to as phyllosilicate, modified by the intercalation of quaternary ammonium groups, and at least one organic phosphate or phosphonate.
  • the polyol component of the formulation for flexible polyurethane foams comprises a stable composition of organoclays in polyols that represents a weight percentage, in relation to the total polyol component, of 10% to 70%.
  • Said stable dispersion of organoclays in polyols contains between 30% and 70% by weight of polyol compound or compounds, between 0.5% and 10% by weight of organoclay, and between 30% and 70% by weight of organic phosphate.
  • the formulation for flexible polyurethane foams is used to produce microcellular flexible foams.
  • the formulation for microcellular flexible foams is for footwear.
  • the formulation for flexible polyurethane foams is applicable to microcellular flexible foams with a density of less than 300 grams/litre.
  • Fig. 1 shows a graph with X-ray diffraction curves for sprayed polyurethane foams produced using formulations comprising a polyol component with a settlement-stable composition of modified organoclay in polyols according to the invention
  • Fig. 2 shows a scanning electronic microscopy (SEM) image at 50 X, achieved using a voltage of 15 V, which aims to show that stable compositions with modified organoclays present a smaller cell size.
  • compositions of organoclays modified by the intercalation of quaternary ammonium groups in polyols that are the object of the invention which comprise at least one polyol compound such as polyol polyester, at least one type of modified organoclay and at least one organic phosphate or phosphonate.
  • Polyester 1 Hoopol F-1398 polyester, produced by Synthesia Espanola S.A., with an IOH (hydroxyl index) of 230-250 mg KOH/g and a viscosity of 200 cps at 60° C.
  • Polyester 2 Hoopol FR-441 polyester, produced by Synthesia Espanola S.A., with an IOH of 75-80 mg KOH/g and a viscosity of 1000 cps at 60° C.
  • Nanofil 2 and Nanofil 32 organoclays modified by the intercalation of quaternary ammonium groups, produced by S ⁇ d Chemie. These are organoclays of the modified montmorillonite type in which the sodium and calcium atoms have been replaced by quaternary ammonium groups or compounds where the substituents of the nitrogen atom are hydrogenated fat, methyl, methyl and benzyl.
  • Example 1 562.5 g of triethyl phosphate and 62.5 g of Nanofil 2 were mixed in a 2- litre spherical reactor. The mixture was heated, stirring at 500 RPM at 90° C. It was then kept at 90° C for 1 hour, subsequently adding 375 grams of the Hoopol F 1398 polyol polyester (polyester 1 ), simultaneously cooling it to reach a temperature of 30° C.
  • the dispersion of modified organoclay in polyol achieved had a hydroxyl index (IOH) of 90 mg KOH/g and a viscosity of 300 cps at 25° C. The dispersion is stable at 3000 RPM for half an hour, with no settling.
  • IOH hydroxyl index
  • Example 2 320 g of triethyl phosphate, 80 g of Nanofil 32 and 300 grams of Hoopol
  • F 1398 (polyester 1) were mixed in a 2-litre spherical reactor. It was heated, stirring at 500 RPM at 90° C. It was then kept at 90° C for 1 hour, subsequently adding 300 grams of the Hoopol F 1398 polyol polyester, simultaneously cooling it to reach a temperature of 30° C.
  • the dispersion achieved had an IOH of 144 mg KOH/g and a viscosity of 500 cps at 25° C. The dispersion is stable at 3000 RPM for half an hour, without any settling at all.
  • Example 3 84.3 g of tris(2-butoxyethyl) phosphate and 9.37 g of Nanofil 2 were mixed in a 2-litre spherical reactor. The mixture was heated, stirring at 500 RPM at 90° C. It was then kept at 90° C for 1 hour, subsequently adding 56.25 g of the Hoopol FR441 polyol polyester (polyester 2), simultaneously cooling it to reach a temperature of 30° C. The dispersion achieved had an IOH of 30 mg KOH/g and a viscosity of
  • the dispersion is stable at 3000 RPM for half an hour, without any settling at all.
  • compositions in Examples 1 to 3 produced polyol components for polyurethane foam systems that were used in formulations for rigid foams and for flexible foams.
  • Said polyol component is commonly referred to as a charge- stabilised polyol component, meaning by charge the dispersions of modified organoclays included therein.
  • polyol components in the examples comprised, in addition to the above-described dispersions of organoclay modified by the intercalation of quaternary ammonium groups in polyols, compounds already known by persons skilled in the art, such as polyethers, compounds with flame retardant properties; surfactants; foaming and gelling catalysts, foaming agents, etc.
  • organoclays that can preferably be used in the settlement-stable compositions of modified organoclay in polyols are those that have particle sizes of 8 to 35 microns and that, as has been previously mentioned, have been produced by chemical modification or the intercalation of quaternary ammonium groups that substitute the original sodium ions of the montmorillonite.
  • modified organoclays produced by the company S ⁇ d Chemie can be used, such as: Nanofil 2, Nanofil 5, Nanofil 8, Nanofil 9, Nanofil 15, Nanofil 32, Nanofil 106, Nanofil 919, Nanofil 948, Nanofil SE3000 or Nanofil SE3010.
  • modified nanoclays such as those produced by the company Southern Clay, with intercalated groups of a similar nature such as: Cloisita 1OA, Cloisita 11 B, Cloisita 15A, Cloisita 2OA, Cloisita 25A, Cloisita 3OB and Cloisita 93A.
  • Nanofil 2 Those that have undergone a sodium ion exchange for a quaternary ammonium group are considered most suitable, where the substituents of the nitrogen atom are: hydrogenated fat, methyl, methyl and benzyl.
  • Nanofil 2 (which differ from Nanofil 32 in terms of their particle size), Cloisita 10A and Cloisita 11B have these characteristics. More preferably, Nanofil 2 is chosen.
  • the polyol compound or compounds of the stable compositions of organoclay in polyols can be of the polyether type or polyester type.
  • polyether type are addition products of propylene oxide or ethylene oxide, or mixtures of both, catalysed in a base medium, on a polyhydroxylated compound that acts as a primer.
  • the molecular weight of the polyethers used in the present invention is between 250 and 12000, and they are prepared by alkoxylation following methods that are widely referred to and described in specialist literature. It is also possible to use non-alkoxylated polyols known as Mannich bases.
  • the polyesters can be all the products resulting from the reaction between a polycarboxylic acid, or a mixture of them, and polyhydroxylated compounds, preferably using dicarboxylic acids and glycols (dihydroxylated compounds), although it is possible to add different proportions of tri- or tetrafunctional components to achieve a functionality of more than two, which is advisable for certain applications. It is also possible to use polyesters based on recycled PET and polyols based on vegetable oils. The molecular weight of the polyesters used in the present invention is between 400 and 5000, and they are prepared by a fusion procedure or by any other methods that are widely referred to and described in specialist literature. These polyols (polyethers and polyesters) are described in "The
  • the organic phosphate or phosphonate is of the type used in fire retardants for rigid polyurethane foams, such as triethyl phosphate (TEP), dimethyl-propyl-phosphonate (DMPP), dihydroxyethyl-methyl-amino-diethyl-phosphonate, TCPP.
  • TEP triethyl phosphate
  • DMPP dimethyl-propyl-phosphonate
  • TCPP dihydroxyethyl-methyl-amino-diethyl-phosphonate
  • chlorine-free materials such as cresyl diphenyl phosphate and tris(2- butoxyethyl) phosphate (TBEP) are suitable phosphate or phosphonate materials, which can be successfully used in flexible foams for footwear.
  • Triethyl phosphate (TEP) is preferred for rigid foams and tris(2-butoxyethyl) phosphate (TBEP) is preferred for flexible foams.
  • Polyester 1 Hoopol F2441 polyester, produced by Synthesia Espanola S.A., with an IOH of 75-80 and a viscosity at 60° C of 900 cps.
  • Polyester 2 Hoopol F110-1000 polyester, produced by Synthesia Espanola
  • Table 1 lists the components of a formulation for a microcellular flexible foam identified as (1).Table 1
  • Table 2 lists the compounds that make up several polyol components (1 ) and (2), which are adapted to react with a respective compound with isocyanate groups in order to produce a rigid polyurethane foam that is adapted to be applied by spraying.
  • the formulated polyol component 1 contains the composition described in example 1.
  • the formulated polyol 2 contains the composition described in example 2.
  • both formulated polyols contain a Mannich base type polyol with a hydroxy!
  • Tegostab B-8453 produced by Degussa
  • foaming catalysts aromatic or aliphatic tertiary amines: pentamethyl diethylene triamine (PMDTA), dimethyl cyclohexylamine (DMCHA) and dimethyl benzylamine (DMBA)
  • a gelling catalyst titanium dibutyldilaureate
  • a hydrofluorocarbon 365mfc/227ea
  • the new stable compositions of organoclays in polyols that do not settle preferably using commercially available modified montmorillonite, such as Nanofil 2 and Nanofil 32 produced by S ⁇ d Chemie, make it possible to produce formulations of rigid polyurethane foams that comply with the Spanish regulations in terms of parameters such as reaction to fire (UNE-EN ISO 13501-1 , EUROCLASS E), or with lower flame heights than in the state of the art (EN-ISO 11925-2), as can be seen in table 2. Furthermore, the properties and appearance of the foam produced are better, presenting a greater dimensional stability and resistance to compression than the same formula without a dispersion of organoclay.

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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)
  • Dispersion Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne une composition stable vis-à-vis de la sédimentation d'une organoargile modifiée dans des polyols, ladite composition comprenant au moins un composé de polyol ; au moins une organoargile modifiée par intercalation de groupements ammonium quaternaire et au moins un phosphate ou phosphonate organique. Ladite composition stable comprend un pourcentage en poids d'organoargile modifiée compris entre 0,5 % et 10 % ; un pourcentage en poids de composé ou composés de polyol compris entre 30 % et 70 % et un pourcentage en poids de phosphate ou phosphonate organique compris entre 30 % et 70 %. L'invention concerne également un composant de polyol pour formulations de mousse de polyuréthanne comprenant la composition stable d'organoargile modifiée dans des polyols ainsi que les mousses de polyuréthanne produites.
PCT/EP2007/002492 2006-03-27 2007-03-21 Nouvelles compositions de polyol et utilisation de celles-ci Ceased WO2007110179A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP07723450A EP1999202A1 (fr) 2006-03-27 2007-03-21 Nouvelles compositions de polyol et utilisation de celles-ci

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ESP200600824 2006-03-27
ES200600824A ES2298026B1 (es) 2006-03-27 2006-03-27 Nuevas composiciones de polioles y uso de las mismas.

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013044474A1 (fr) * 2011-09-29 2013-04-04 Dow Global Technologies Llc Utilisation de phosphate de trialkyle comme suppresseur de fumée dans de la mousse de polyuréthane
EP2690118A1 (fr) * 2012-07-27 2014-01-29 Basf Se Polyuréthane contenant des composés phosphorés

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0361764A2 (fr) * 1988-09-28 1990-04-04 Imperial Chemical Industries Plc Composition contenant des composants contenant des hydrogènes réactifs à l'isocyanate
WO2006003421A1 (fr) * 2004-07-02 2006-01-12 University Of Strathclyde Mousses de polyuréthane nanocomposite souples ignifugées
WO2006060174A1 (fr) * 2004-11-15 2006-06-08 Honeywell International Inc. Mousses polymeres a base d'isocyanate avec des materiaux a nano-echelle

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20020017569A (ko) * 2000-08-31 2002-03-07 구광시 클레이를 포함하는 폴리우레탄 및 이의 제조방법
AU2003235694A1 (en) * 2002-01-21 2003-07-30 Huntsman International Llc Nano composite materials with enhanced properties
DE10351268A1 (de) * 2003-10-31 2005-06-02 Basf Ag Modifizierte Schichtsilikate und Polyurethane, enthaltend exfolierte Schichtsilikate
JP4431875B2 (ja) * 2004-02-02 2010-03-17 株式会社ブリヂストン 軟質ポリウレタン発泡成形体の製造方法、軟質ポリウレタン発泡成形体、及び車両用シート

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0361764A2 (fr) * 1988-09-28 1990-04-04 Imperial Chemical Industries Plc Composition contenant des composants contenant des hydrogènes réactifs à l'isocyanate
WO2006003421A1 (fr) * 2004-07-02 2006-01-12 University Of Strathclyde Mousses de polyuréthane nanocomposite souples ignifugées
WO2006060174A1 (fr) * 2004-11-15 2006-06-08 Honeywell International Inc. Mousses polymeres a base d'isocyanate avec des materiaux a nano-echelle

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CAO X ET AL: "Polyurethane/clay nanocomposites foams: processing, structure and properties", POLYMER, ELSEVIER SCIENCE PUBLISHERS B.V, GB, vol. 46, no. 3, 26 January 2005 (2005-01-26), pages 775 - 783, XP004705996, ISSN: 0032-3861 *

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013044474A1 (fr) * 2011-09-29 2013-04-04 Dow Global Technologies Llc Utilisation de phosphate de trialkyle comme suppresseur de fumée dans de la mousse de polyuréthane
EP2760928A4 (fr) * 2011-09-29 2015-06-17 Dow Global Technologies Llc Utilisation de phosphate de trialkyle comme suppresseur de fumée dans de la mousse de polyuréthane
EP2690118A1 (fr) * 2012-07-27 2014-01-29 Basf Se Polyuréthane contenant des composés phosphorés
WO2014016167A1 (fr) * 2012-07-27 2014-01-30 Basf Se Mousses de polyuréthane contenant des composés du phosphore

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