WO2014037558A1 - Procédé pour la préparation d'une composition de polyol - Google Patents

Procédé pour la préparation d'une composition de polyol Download PDF

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Publication number
WO2014037558A1
WO2014037558A1 PCT/EP2013/068591 EP2013068591W WO2014037558A1 WO 2014037558 A1 WO2014037558 A1 WO 2014037558A1 EP 2013068591 W EP2013068591 W EP 2013068591W WO 2014037558 A1 WO2014037558 A1 WO 2014037558A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyol
polymer
polyols
catalyst
mixing
Prior art date
Application number
PCT/EP2013/068591
Other languages
English (en)
Inventor
Nirupaplava METTA
Pranaya Man Singh PRADHAN
Ritika THAKUR
Original Assignee
Shell Internationale Research Maatschappij B.V.
Shell Oil Company
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 Shell Internationale Research Maatschappij B.V., Shell Oil Company filed Critical Shell Internationale Research Maatschappij B.V.
Publication of WO2014037558A1 publication Critical patent/WO2014037558A1/fr

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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
    • C08G18/0838—Manufacture of polymers in the presence of non-reactive compounds
    • C08G18/0842—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents
    • C08G18/0861—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers
    • C08G18/0871—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic
    • C08G18/0876—Manufacture of polymers in the presence of non-reactive compounds in the presence of liquid diluents in the presence of a dispersing phase for the polymers or a phase dispersed in the polymers the dispersing or dispersed phase being organic the dispersing or dispersed phase being a polyol
    • 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
    • C08G18/16—Catalysts
    • C08G18/22—Catalysts containing metal compounds
    • C08G18/24—Catalysts containing metal compounds of tin
    • C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
    • C08G18/3271—Hydroxyamines
    • C08G18/3278—Hydroxyamines containing at least three hydroxy groups
    • C08G18/3281—Hydroxyamines containing at least three hydroxy groups containing three 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
    • C08G18/40—High-molecular-weight compounds
    • C08G18/409—Dispersions of polymers of C08G in organic compounds having active hydrogen
    • 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
    • C08G18/4833—Polyethers containing oxyethylene units
    • C08G18/4837—Polyethers containing oxyethylene units and other oxyalkylene units
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • C08G18/6666—Compounds of group C08G18/48 or C08G18/52
    • C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
    • C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
    • C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
    • C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
    • C08G18/7614—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring
    • C08G18/7621—Polyisocyanates or polyisothiocyanates cyclic aromatic containing only one aromatic ring being toluene diisocyanate including isomer mixtures
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0041—Foam properties having specified density
    • C08G2110/005—< 50kg/m3
    • 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
    • C08G2110/00—Foam properties
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

  • the present invention provides a process for the preparation of a polymer-modified polyol, wherein the polymer-modified polyol comprises a
  • the present invention further provides a process for the preparation of polyurethane foam by reacting the product thus formed with organic polyisocyanate in the presence of a blowing agent, a polyurethane catalyst, optionally crosslinking agents and also optionally further usual auxiliaries .
  • a stable PIPA polymer polyol composition can be produced by a process which involves initial reaction of the olamine and the polyisocyanate in the presence of a limited amount of the polyol .
  • Such a polymer polyol composition can be used to produce polyurethane foams with good hardness properties. Such foams may also exhibit a high degree of fire resistance
  • polyisocyanates are aromatic polyisocyanates, for example toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI) which are aromatic polyisocyanates.
  • aromatic polyisocyanates for example toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI) which are aromatic polyisocyanates.
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • diphenylmethane-2 , 4 ' , 2, 2', 4, 4 ' -diisocyanates and mixtures thereof (generally referred to as pure MDI) in crude, pure or polymeric form, for example, a mixture containing from 70 to 100%, especially 80%, by weight of the 4, 4 '-isomer and from 0 to 30%, especially 20%, by weight of the 2, 4 '-isomer; mixtures of MDI with
  • trimethylolpropane dipropylene glycol or tripropylene glycol; and polyisothiocyanates , polyisoselenocyanates and mixtures thereof.
  • diisopropanolamine triisopropanolamine, N- methylisopropanolamine, N-ethylisopropanolamine, N- propylisopropanolamine .
  • Substituted alkanolamines may also be used.
  • a preferred alkanolamine is
  • the polymerisation of the olamine with the organic polyisocyanate may be catalysed using any of the
  • the catalyst is stannous octoate.
  • the catalyst of choice is dibutyl-tin-dilaurate .
  • said catalyst has known HSSE risks.
  • An additional advantage of the present invention is that a less harmful catalyst, such as stannous octoate can be used effectively.
  • the polyol which is present in the polymer-modified polyol can be any polyol prepared from hydroxyl
  • the polyol for use in the process of the present invention is a polyalkoxylated polyol prepared by reacting a hydroxyl containing starting material compound with propylene oxide, optionally also with one or more other alkylene oxides such as ethylene oxide, butylenes oxide and/or mixtures thereof.
  • a hydroxyl containing starting material compound e.g., ethylene oxide, butylenes oxide and/or mixtures thereof.
  • polyalkoxylated polyol is prepared by reacting a hydroxyl containing starting material compound with propylene oxide either on its own or as a mixture with ethylene oxide in a ratio suitable to achieve the desired level of secondary hydroxyl groups .
  • Preferred hydroxyl containing starting material compounds for the polyol present in the polymer modified polyol generally contain from 2 to 8 hydroxyl groups.
  • alcohols comprise glycols, glycerol, pentaerythritol, trimethylolpropane, triethanolamine, sorbitol and mannitol.
  • a strong base like potassium hydroxide or a similar metal hydroxide salt is used as a catalyst in the reaction of the hydroxyl containing starting material compounds with the alkylene oxide (s) .
  • catalysts such as double metal cyanide complex catalysts can also be used.
  • the present invention also relates to a process for the preparation of a polyurethane foam by reacting the polymer modified polyol with an organic polyisocyanate in the presence of a blowing agent, a polyurethane catalyst, optionally, crosslinking agents and, also optionally, further usual auxiliaries .
  • polyisocyanates are aromatic polyisocyanates, for example toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI) which are aromatic polyisocyanates.
  • aromatic polyisocyanates for example toluene diisocyanate (TDI) and diphenylmethane diisocyanate (MDI) which are aromatic polyisocyanates.
  • TDI toluene diisocyanate
  • MDI diphenylmethane diisocyanate
  • isocyanate-ended prepolymers for example, reaction products of a diisocyanate with a deficiency of one or more low molecular weight polyols such as
  • trimethylolpropane dipropylene glycol or tripropylene glycol; and polyisothiocyanates , polyisoselenocyantes and mixtures thereof.
  • blowing agents such as carbon dioxide and/or methylene chloride, can be used as well either per se or in combination with water.
  • water is the blowing agent in the formulation according to the present invention .
  • At least one polyurethane catalyst is used in the process for the preparation of polyurethane foam.
  • Preferably more than one catalyst is used.
  • Polyurethane catalysts are known in the art and include many different compounds. Such catalysts include those used for the preparation of the polymer-modified polyol. An extensive list of polyurethane catalysts is, for instance, given in
  • Gelation catalysts are catalysts which predominantly promote the gelation of the foaming mixture, i.e. which promote the reaction between polyols and polyisocyanate.
  • Typical gelation catalysts are stannous octoate and dibutyltindilaurate .
  • Blowing catalysts predominantly promote the CO/H2O reaction, whereby carbon dioxide is released which causes the blowing to occur.
  • Typical blowing catalysts are dimethylaminoethylether and urea.
  • the flame retardants can be liquid and/or solid flame retardants.
  • Organosilicone surfactants are most conventionally applied as foam stabilisers in polyurethane production . A large variety of such organosilicone surfactants is commercially available. Preferred compounds include compound L2100, commercially available from Momentive, and compound B4900,
  • the present invention is further illustrated in the Examples .
  • TEOA triethanolamine
  • Snoct stannous octoate
  • Example 2 PIPA 2 - of the Invention
  • SC48-08 is a glycerine-initiated polyol containing about 12.2% EO distributed randomly along the chain and having an approximate hydroxyl value of 48mg KOH/g polyol. It contains about 10% primary hydroxyl end- groups, the remainder of the hydroxyl-end groups are secondary .
  • the polymer modified polyols made in Examples 1 and 2 were used to make polyurethane foams in Examples 3 and 4, respectively.
  • SAN polyol also containing 10wt% solids, was converted into a polyurethane foam using an equivalent process.
  • the foam was made by mixing the polymer modified polyol with water, Al, A33, B4900 and Snoct in amounts according to Table 2. After mixing, TDI was added. TDI was then added and the foam processing was carried out under the conditions indicated in Table 3. Table 4 shows the physical properties of the resultant foams.
  • SP30-45 is a SAN
  • PIPA refers to the polymer modified polyols made in Examples 1 and 2. Thus, in Example 3 it refers to PIPAl and in Example 4 it refers to PIPA2.
  • Al is a blowing catalyst (Ex - Momentive) containing bis (2- dimethylaminoethyl ether.
  • A33 is aminic catalyst (Ex - Momentive) containing 30% triethylene diamine and 60% DPG .
  • B4900 is a silicone stabilizer for polyurethane foaming (Ex- Evonik) .
  • RH refers to relative humidity
  • CLD compression load density
  • the process of the present invention thus provides desirable high hardness foams by a facile method, avoiding the more complex preparation required and the limited availability issues involved in foams made from SAN polyols.

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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)
  • Engineering & Computer Science (AREA)
  • Manufacturing & Machinery (AREA)
  • Polyurethanes Or Polyureas (AREA)

Abstract

La présente invention concerne un procédé pour la préparation d'un polyol modifié par polymère, le polyol modifié par polymère comprenant un polymère de polyuréthane dérivé de la réaction d'une olamine avec un polyisocyanate organique et un polyol qui comprend au moins 50 % en poids de groupes hydroxyle secondaires et le procédé comprenant les étapes de : (a) mélange de l'olamine avec une quantité du polyol dans la plage de 30 à 80 % en poids du polyol total ; (b) ajout d'un catalyseur et du polyisocyanate sous mélange ; (c) ensuite, ajout de la partie résiduelle du polyol ; et (d) mélange des réactifs jusqu'à ce que la réaction soit complète.
PCT/EP2013/068591 2012-09-10 2013-09-09 Procédé pour la préparation d'une composition de polyol WO2014037558A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP12183664 2012-09-10
EP12183664.7 2012-09-10

Publications (1)

Publication Number Publication Date
WO2014037558A1 true WO2014037558A1 (fr) 2014-03-13

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Family Applications (1)

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Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015038827A1 (fr) * 2013-09-13 2015-03-19 Dow Global Technologies Llc Mousse souple classique à base de pipa-polyol
WO2015038825A1 (fr) 2013-09-13 2015-03-19 Dow Global Technologies Llc Procédé de fabrication de polyol-polyisocyanatedepolyaddition au moyen de stabilisants
WO2015038826A1 (fr) 2013-09-13 2015-03-19 Dow Global Technologies Llc Procédé de production d'un polyol par polyaddition de polyisocyanate et produit obtenu
US9783633B2 (en) 2013-09-13 2017-10-10 Dow Global Technologies Llc PIPA polyol based viscoelastic foams
US9840579B2 (en) 2013-09-13 2017-12-12 Dow Global Technologies Llc Thixotropic polyol compositions containing dispersed urethane-modified polyisocyanurates

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2072204A (en) * 1980-02-14 1981-09-30 Rowlands J P Polymer-modified polyols useful in polyurethane manufacture
US5955534A (en) * 1995-11-30 1999-09-21 Arco Chemical Technology, L.P. Process for the preparation of polymer polyol dispersions
WO2008116605A1 (fr) * 2007-03-24 2008-10-02 Fritz Nauer Ag Mousse de polyuréthane

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2072204A (en) * 1980-02-14 1981-09-30 Rowlands J P Polymer-modified polyols useful in polyurethane manufacture
US5955534A (en) * 1995-11-30 1999-09-21 Arco Chemical Technology, L.P. Process for the preparation of polymer polyol dispersions
WO2008116605A1 (fr) * 2007-03-24 2008-10-02 Fritz Nauer Ag Mousse de polyuréthane

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015038827A1 (fr) * 2013-09-13 2015-03-19 Dow Global Technologies Llc Mousse souple classique à base de pipa-polyol
WO2015038825A1 (fr) 2013-09-13 2015-03-19 Dow Global Technologies Llc Procédé de fabrication de polyol-polyisocyanatedepolyaddition au moyen de stabilisants
WO2015038828A1 (fr) 2013-09-13 2015-03-19 Dow Global Technologies Llc Mousse de polyuréthane à base de pipa à combustion modifiée
WO2015038826A1 (fr) 2013-09-13 2015-03-19 Dow Global Technologies Llc Procédé de production d'un polyol par polyaddition de polyisocyanate et produit obtenu
US9783633B2 (en) 2013-09-13 2017-10-10 Dow Global Technologies Llc PIPA polyol based viscoelastic foams
US9840579B2 (en) 2013-09-13 2017-12-12 Dow Global Technologies Llc Thixotropic polyol compositions containing dispersed urethane-modified polyisocyanurates
US9840603B2 (en) 2013-09-13 2017-12-12 Dow Global Technologies Llc PIPA based combustion-modified flexible foam
US9840602B2 (en) 2013-09-13 2017-12-12 Dow Global Technologies Llc PIPA polyol based conventional flexible foam
US9840578B2 (en) 2013-09-13 2017-12-12 Dow Global Technologies Llc Polyisocyanate polyaddition polyol manufacturing process and product
US10017599B2 (en) 2013-09-13 2018-07-10 Dow Global Technologies Llc Polyisocyanate polyaddition polyol manufacturing process using stabilizers

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