WO1994002525A1 - Amines a modification isocyanate utilisees a titre de catalyseurs pour la preparation de matieres polyurethanes - Google Patents

Amines a modification isocyanate utilisees a titre de catalyseurs pour la preparation de matieres polyurethanes Download PDF

Info

Publication number
WO1994002525A1
WO1994002525A1 PCT/EP1993/001845 EP9301845W WO9402525A1 WO 1994002525 A1 WO1994002525 A1 WO 1994002525A1 EP 9301845 W EP9301845 W EP 9301845W WO 9402525 A1 WO9402525 A1 WO 9402525A1
Authority
WO
WIPO (PCT)
Prior art keywords
polyol
amine
isocyanate
catalyst
reactive
Prior art date
Application number
PCT/EP1993/001845
Other languages
English (en)
Inventor
Francois Marie Casati
Reinold RISTEMA VAN ECK
Original Assignee
Polyol International B.V.
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 Polyol International B.V. filed Critical Polyol International B.V.
Priority to AU45687/93A priority Critical patent/AU4568793A/en
Publication of WO1994002525A1 publication Critical patent/WO1994002525A1/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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • C08G18/1841—Catalysts containing secondary or tertiary amines or salts thereof having carbonyl groups which may be linked to one or more nitrogen or oxygen atoms
    • 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
    • C08G18/1825—Catalysts containing secondary or tertiary amines or salts thereof having hydroxy or primary amino 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
    • C08G2110/00—Foam properties
    • C08G2110/0008—Foam properties flexible
    • 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
    • C08G2110/0016—Foam properties semi-rigid
    • 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
    • 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 relates to a method of producing polyurethane materials by employing as a catalyst or co-catalyst an isocyanate modified amine which is prepared by reacting a tertiary amine containing a reactive hydrogen, a polyisocyanate and a polyol.
  • the present invention also relates to polyurethane materials produced by the above method.
  • Tertiary amines are widely used as catalysts for the production of polyurethane foams, elastomers and coatings because they act to accelerate both water- isocyanate and polyol-isocyanate reactions.
  • Parameters to consider in selecting a tertiary amine catalyst are : basicity, steric hindrance of the amine nitrogen(s), volatility, hydrophylicity and solubility in the other raw materials used for the production of polyurethane materials.
  • tertiary amines which do not contain active hydrogen sites (non-reactive tertiary amines) is often associated with problems of odor, toxicity, and staining of polyvinyl chloride (PVC) material molded against polyurethane foam. These tertiary amines have a strong odor which is carried over to the final polyurethane material. Potential inhalation toxicity of tertiary amines is also well known.
  • Tertiary amines containing active hydrogen sites were thought to offer solution to the problems of odor, toxicity, and staining of the PVC material associated with non-reactive tertiary amines.
  • amine catalysts containing hydroxyl groups and/or secondary or primary amines are generally less active than the corresponding alkyl substituted derivatives. Furthermore, studies of 0 reactive amine catalysts containing hydroxyl groups have shown that amines with primary hydroxyl groups are more effective catalysts than those with secondary hydroxyl groups and those in turn are more effective than the analogous catalysts with tertiary hydroxyl groups.
  • amine catalysts containing a primary or secondary amine group are not effective in reducing staining of PVC. This is surprising because reactive amine catalysts were expected to react with the isocyanate component and become part of the polyurethane backbone. Thus, it appears that reactive amine catalysts are not totally bound to the polyurethane backbone during the isocyanate-water and isocyanate-polyol reactions but rather form, in the same way as their corresponding alkyl derivatives, complexes with isocyanates and water, and are released when polyurethane reactions proceed.
  • Plasticized PVC and Polyurethane Foam by A.S. Wilson, et al., Plastics and Rubber International, Vol. 13 No. 1, February 1988.
  • US Patent 3,325,421 E. Muller
  • US Patent 4,089,835 K. K ⁇ nig et al
  • US Patent 4,093,569 A. Reiscril et al
  • US Patent 4,089,835 also mentions the potential use of monofunctional amines or alkanolamines but only as chain terminators.
  • US Patent 4,041,019 and US Patent 4,007,140 describe polyurethane catalysts obtained by a modification of an amine with an isocyanate.
  • the modified amines are 2-methylimidazole and 3-dimethyl- amino propylamine, respectively.
  • no polyol is present and therefore no linkage with a high molecular weight chain is disclosed or hinted.
  • European Patent 0,376 602 describes the alkoxylation of triamines and their use as polyurethane catalysts.
  • US Patent 4,040,992 discloses reactive amines modified by quaternarization.
  • isocyanate modified amines produced by reacting a tertiary amine containing a reactive hydrogen, a polyisocyanate and a polyol show comparable or enhanced catalytic activity compared with the corresponding non-modified amines.
  • the present invention concerns an isocyanate modified amine catalyst prepared by intimately mixing under reaction conditions a reactive tertiary amine, a polyol, and an organic isocyanate compound.
  • the present invention concerns a process for the preparation of a polyurethane material whic-h comprises intimately mixing under reaction conditions a polyol, an organic isocyanate compound, at least one catalyst for the urethane forming reaction and, optionally, a blowing agent and/or one or more additives wherein said at least one urethane forming catalyst comprises an isocyanate modified reactive amine prepared by the aforementioned process.
  • the present invention concerns a polyurethane material prepared by aforementioned process.
  • the isocyanate modified amine useful -as a catalyst or co-catalyst in the process of the present invention is prepared by blending, in a suitable reaction vessel, a polyol and a reactive amine for a period of time from about several seconds to about several minutes, preferably from about 10 seconds to about 1 minute, most preferably from about 20 seconds to about 30 seconds, while stirring the blend. Then, while stirring the blend, a polyisocyanate is slowly added to the blend and the resulting reaction mixture is stirred for additional period of time of from about several seconds to about several minutes, preferably from about
  • the resultant isocyanate modified amine can be a liquid of various viscosity or a gel. If this blending is made with a mixing head, these times can be reduced to a couple of seconds.
  • any amine containing both tertiary nitrogen(s) and active hydrogen(s) can be employed in the present invention as the reactive amine.
  • these amines contain at least one dialkyl, preferably dimethyl, amino group or one amidine function.
  • the chain between the active hydrogen and the nitrogen(s) can be of any length, preferably between 2 and 5 carbons with or without ether functions between them.
  • the active hydrogen is derived from an -OH group, a -NH group, or any chemical structure listed by Saunders and Frisch in “Polyurethanes” , Part I, pages 65 to 88.
  • the active hydrogen is derived from an -OH or a -NH group.
  • Suitable amines containing a reactive hydrogen are, for example, N,N-dimethylamino ethanol; N,N-dimethylamino propanol; N,N,N'-trimethyl- N'-( 2-hydroxyethyl)ethylene diamine; 2-methyl-8-( 3- hydroxypropyl)-2,8-diaza-5-oxanonane; N,N,N'-trimethyl- '-(hydroxypropyl)ethylene diamine; 2-methyl-8-(2- hydroxypropyl)ethylene diamine; 2-methyl-8-(2- hydroxyethyl)-2,8-diaza-5-oxanonane; N,N,N'-t imethy1- N'-(ethoxyethanol)-ethylene diamine; 2- ⁇ N,N- dimethylamino)ethyoxyethanol; 1, 5,7-triazabicyclo- (4,4,0)-dec-5-ene; N,N-dimethylaminopropyl amine;
  • the isocyanates which can be used in the preparation of the modified amine useful in the present invention are polyfunctional isocyanates well known to those skilled in the art. Suitable polyisocyanates include aliphatic, cycloaliphatic and aromatic polyfunctional, particularly bifunctional , isocyanates.
  • aliphatic diisocyanates having between 2 and 18 carbon atoms, preferably between 4 and 12 carbon atoms, such as ethylene diisocyanate, 1,4-tetramethylene diisocyanate, 1,6-hexa-methylene diisocyanate and 1,12- dodecane diisocyanate; cycloaliphatic diisocyanates having between 2 and 18 carbon atoms, preferably between 4 and 12 carbon atoms, such as cyclohexane-1,3- diisocyanate, cyclohexane-l,4-diisocyanate as well as any desired mixture thereof, l-isocyanato-3,3,5-tri- methyl-5-isocyanatomethylcyclohexane; 2,4- and 2,6-hexa- hydrotoluene diisocyanate as well as any desired mixture of these isomers; 4,4'- and 2,4 '-diisocyanatodicyclo- hexylme
  • the reactive amine and the isocyanate are employed in a molar ratio of 0.1 to 10.
  • Polyols which are suitable for use in the preparation of the modified amine useful in the present invention are polyether polyols and polyester polyols. These polyols are well known and are readily available. Polyether polyols are preferred.
  • the term polyether polyol includes alkylene oxide adducts of low molecular weight diols or triols of naturally occurring polyols and non-reducing sugars and derivatives thereof, having molecular weight between 500 and 15,000, preferably 1,000 to 6,000.
  • Suitable polyether polyols can be prepared by adding an alkylene oxide to an initiator containing at least one and preferably two or more active hydrogen atoms.
  • polyether polyols suitable for use in the present invention include those products sold by The Dow Chemical Company under the trademarks VORANOL and VORALUX such as, for example, VORANOL CP-6001, VORANOL CP-3322, VORANOL CP-4702, VORALUX HF-500, and the like.
  • Other suitable polyols for use in the present invention include PHD -, PIPA - or SAN - type copolymer polyols. These polyols known as polymer polyols are commercially available.
  • Illustrative of commercially available SAN - type copolymer polyols suitable for use in the present invention include those products sold by The Dow Chemical Company under the trademark SPECFLEX such as, for example, SPECFLEX NM 800.
  • Mixtures of one or more polyether polyols 10 and/or one or more polymer polyols are also suitable for use in the present invention.
  • the isocyanate modified amines prepared as described hereinabove have good heat stability and once ic incorporated in the polyurethane matrix do not migrate with time or under high temperature conditions.
  • the polyol(s), polyisocyanate, the hereinbefore described modified amine catalyst and, optionally, foaming agent and/or other components are contacted, thoroughly mixed and permitted to react and to expand and cure into a polyurethane material.
  • the particular mixing apparatus is not critical, and various types of mixing head and spray apparatus are conveniently used. It is often convenient, but not necessary, to preblend certain of the raw materials prior to reacting the polyisocyanate and polyol components. For example, it is often useful to blend the polyol(s), a suitable foaming agent, catalyst (s) and other components except for polyisocyanate(s) , and then contact this mixture with the polyisocyanate.
  • all components can be introduced individually to the mixing zone where the polyisocyanate(s) and polyol(s) are contacted. It is also possible to prereact all or a portion of the polyol(s) with the polyisocyanate(s) to form a prepolymer.
  • Suitable polyols and/or polymer polyols which can be used to produce the polyurethane materials of the present invention are well known in the art and include those hereinbefore described and any other commercially available polyol and/or polymer polyol. Mixtures of one or more polyols and/or one or more polymer polyols may also be used. to produce the polyurethane materials according to the present invention.
  • the hereinbefore described modified reactive amine catalyst can be used alone or in combination with known urethane catalysts.
  • Exemplary of known catalysts which can be used in combination with the modified reactive amines of the present invention are amines, reactive or non- reactive, with aminated crosslinkers such as for instance urea, triethanolamine, and methyl diethanolamine or organometallic compounds such as tin, bismuth, or zinc compounds and the like.
  • the levels of urethane catalysts used are conventional, but typically, depending on the specific catalyst, will be present in an amount of from 0.001 to 10.0, preferably from 0.01 to 5.0, most preferably 0.05 to 3.0 parts by weight.
  • Foaming agents which can be used to prepare polyurethane materials according to the present
  • exemplary of physical foaming agents which may be used include, for example, the halogenated hydrocarbons such as methylene chloride, -.5 trichlorofluoromethane, dichlorotrifluoroethane, chlorodifluoroethane; hydrocarbons such is pentane and hexane; and entrained gases such as air, nitrogen and carbon dioxide.
  • halogenated hydrocarbons such as methylene chloride, -.5 trichlorofluoromethane, dichlorotrifluoroethane, chlorodifluoroethane
  • hydrocarbons such is pentane and hexane
  • entrained gases such as air, nitrogen and carbon dioxide.
  • the foaming agent when used may be present in an amount to provide the resulting polyurethane foam with an overall density of from 15 to 500 kg/m3.
  • surfactants such as, for example, Silicone Union Carbide SH-209 product sold by Union Carbide Corporation
  • chain extending agents such as, for example, ethylene glycol, 30 1 ,4-butanediol, diethanolamine, diisopropanolamine and polyamine
  • fillers such as, for example, melamine; pigments and dyes; and the like.
  • the polyurethane materials prepared according to the present invention can be foams, with densities ranging between 15 and 500 kg/m.3, molded or free rise, flexible, semi-flexible or rigid, integral skin, or microcellular foams, elastomers or coatings.
  • DEOA is diethanolamine
  • BDMPA is bis(dimethylaminopropyl) amine.
  • TMHED is N, N, N'-trimethyl-N'-(2-hydroxyethyl) ethylene diamine.
  • DMAEE is 2-(dimethylaminoethoxy)ethanol.
  • MHEDON is 2-methyl-8-(2-hydroxyethyl)-2,8- diaza-5-oxanonane.
  • TDI is toluene diisocyanate.
  • TDI 80/20 is a mixture of 2,4- and 2,6- TDI in 80% - 20% ratio.
  • MDI is diphenylmethane diisocyanate.
  • PMDI is polymeric MDI.
  • M-309 is liquid MDI derivative having functionality of 2.2 and an isocyanate content of 32.3% sold by The Dow Chemical Company under the trademark ISONATE M-309.
  • M-220 is polymeric MDI having an average functionality of 2.7 and isocyanate content of 30.9% sold by The Dow Chemical Company under the trademark VORANATE M-220.
  • VM-50 is a blend of polymeric MDIs sold by Imperial Chemical Industries under the trademark SUPRASEC VM-50.
  • CP-3322 is a polyol having OH number of 48 and Average Molecular Weight of 3500 sold by The Dow Chemical Company under the trademark VORANOL CP-3332.
  • CP-1421 is a polyol having OH number of 33 and Average Molecular Weight of 5000 sold by The Dow Chemical Company under the trademark VORANOL CP-1421.
  • CP-4702 is a polyol having OH number of 35 and Average Molecular Weight of 4800 sold by The Dow Chemical Company under the trademark VORANOL CP-4702.
  • CP-6001 is a polyol having OH number of 27 and Average Molecular Weight of 6200 sold by The Dow Chemical Company under the trademark VORANOL CP-6001.
  • HF-500 is a polyol having OH number of 35 and Average Molecular Weight of 4800 sold by- The Dow Chemical Company under the trademark VORALUX HF 500.
  • CA-560-1 is a polyol sold by Shell Chemicals under the trademark CARADOL 560-1.
  • NM-800 is a SAN copolymer polyol sold by The Dow Chemical Company under the trademark SPECFLEX NM- 800.
  • NC-604 is a SAN copolymer polyol sold by The Dow Chemical Company under the trademark SPECFLEX NC- 604.
  • 33LV is a 33 percent solution of triethylene diamine in dipropylene glycol sold by Air Products and Chemicals Inc. under the trademark DABCO 33LV.
  • A-l is 70% bis(2-dimethylaminoethyl)ether solution in DPG, an amine catalyst, sold by Union Carbide Corporation under the trademark NIAX A-l.
  • SH-210 and SH-209 are silicone surfactants sold by Union Carbide Corporation under the trademark Union Carbide SH-210 and Union Carbide SH-209 silicones.
  • DA-660 is a mold release agent sold by Grace Teroson under the trademark DARALESE 660.
  • LK-260 is a mold release agent sold by Th. Goldschmidt.
  • CT cream time in seconds.
  • GT gel time in seconds.
  • wet CS is wet compression set at 70% CD with skin determined according to Renault test RP-16.37-81.
  • HACS is humid aged compression set at 75% CT determined according to ISO, BS 4443,79.
  • Catalyst A In a 250 ml glass bottle equipped with a magnetic stirrer CP-3322 (100 grams) and BDMPA (50 grams) were blended together for 30 seconds with stirring. Then, without stopping the stirring, TDI 80/20 (23.2 grams) was added slowly for 7 seconds to the blend and stirring was continued for another 30 seconds. Temperature rose to 66° C after 1 minute and then decreased to 35° C after 12 minutes. The resulting catalyst is designated as Catalyst A.
  • High resilience polyurethane foam was prepared by employing the following procedure:
  • Free-Rise Reactivity cream time gel time (s) rise time (s) settle (mm)
  • the prepared modified amine catalysts were left at room temperature for several days before using them in the preparation of polyurethane foams.
  • the prepared modified amine catalysts were left at room temperature for several days before using them in the preparation of polyurethane foams.
  • CP-3322 (10 grams) and TDI 80/20 (2.3 grams) were mixed together with stirring for 30 seconds and then BDMPA (2.5 grams) was added while stirring was continued. The resulting solution became quickly viscous and a gel was formed after cooling.
  • a sample of unaged Catalyst AE was also subjected to infrared spectroscopy to determine the existence of free isocyanate groups. No > presence of any free isocyanate group was detected in unaged Catalyst AE by infrared spectroscopy.
  • High resilience molded polyurethane foams were prepared according to the procedure described in Example IB using the formulation given in Table 8 below. Demold time was 5 minutes.
  • Semi-rigid molded polyurethane foam was prepared using Kraus Maffei machine model KM-40. The foam formulation and foaming conditions are given in Table 10 below. DA-660 was used as the mold release agent. Demold time was 5 minutes. Table 10
  • Cream time (s) 6 Gel time (s) 62 Rise time (s) 120 Free rise density 39.2 kg/m 3 Molded density 120 kg/m3
  • Foam B a piece of foam produced using conventional reactive amine catalyst was also wrapped in a PVC foil which was then welded around it. This PVC wrapped foam is designated Foam B. Ageing tests were run on both Foam A and Foam B in an oven for 500 hours at 80° C. Then using a Minolta Chromometer CR 200 and taking an unaged PVC sample as reference the change in color and lightness of the PVC sample, in contact with Foam A and Foam B was measured. Results are given in Table 11 below.

Landscapes

  • 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

Un catalyseur sous forme d'amine à modification isocyanate est préparé en effectuant le mélange intime, dans des conditions de réaction, d'une amine tertiaire réactive, d'un polyol et d'un composé d'isocyanate organique. Ladite amine à modification d'isocyanate est utilisée pour la préparation de matières polyuréthanes, par exemple les mousses à masse volumique comprise entre 15 et 500 kg/m3, moulées ou à foisonnement libre, souples, semi-souples ou rigides, à peau intégrale, ou des mousses microcellulaires, des élastomères ou des enrobages.
PCT/EP1993/001845 1992-07-21 1993-07-14 Amines a modification isocyanate utilisees a titre de catalyseurs pour la preparation de matieres polyurethanes WO1994002525A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU45687/93A AU4568793A (en) 1992-07-21 1993-07-14 Isocyanate modified amines as catalysts useful for the preparation of polyurethane materials

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB929215488A GB9215488D0 (en) 1992-07-21 1992-07-21 Isocyanate modified amines as catalysts useful for the preparation of polyurethane materials
GB9215488.9 1992-07-21

Publications (1)

Publication Number Publication Date
WO1994002525A1 true WO1994002525A1 (fr) 1994-02-03

Family

ID=10719055

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP1993/001845 WO1994002525A1 (fr) 1992-07-21 1993-07-14 Amines a modification isocyanate utilisees a titre de catalyseurs pour la preparation de matieres polyurethanes

Country Status (3)

Country Link
AU (1) AU4568793A (fr)
GB (1) GB9215488D0 (fr)
WO (1) WO1994002525A1 (fr)

Cited By (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996006873A1 (fr) * 1994-08-31 1996-03-07 Smith & Nephew Plc Catalyseurs integres par liaison chimique
WO1997010275A1 (fr) * 1995-09-13 1997-03-20 Smith & Nephew Plc Compositions durcissables
US6387972B1 (en) 2001-02-15 2002-05-14 Crompton Corporation Process to enhance polyurethane foam performance
WO2002048229A2 (fr) * 2000-11-10 2002-06-20 Crompton Corporation Procede pour ameliorer les performances d'une mousse de polyurethanne
US6762274B2 (en) 2000-02-10 2004-07-13 Dow Global Technologies Inc. Low emission polyurethane polymers made with autocatalytic polyols
US6818675B2 (en) 2002-08-06 2004-11-16 General Electric Company Process for preparing polyurethane foam
US6924321B2 (en) 2001-08-16 2005-08-02 Dow Global Technologies Inc. Polyols with autocatalytic characteristics and polyurethane products made therefrom
US7361695B2 (en) 2001-08-15 2008-04-22 Dow Global Technologies Inc. Process to manufacture flexible polyurethane foams
EP3190133A1 (fr) 2005-11-14 2017-07-12 Dow Global Technologies Llc Procede de moulage de mousses polyurethane rigides avec une meilleure conductivite thermique

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1040233B (de) * 1955-11-18 1958-10-02 Hudson Foam Plastics Corp Verfahren zum Herstellen eines elastischen Schaumstoffes mit im wesentlichen offenen Zellen auf Polyester-Isocyanat-Basis
FR2080960A1 (fr) * 1970-02-05 1971-11-26 Bayer Ag
FR2085965A1 (fr) * 1970-04-09 1971-12-31 Dow Chemical Co

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1040233B (de) * 1955-11-18 1958-10-02 Hudson Foam Plastics Corp Verfahren zum Herstellen eines elastischen Schaumstoffes mit im wesentlichen offenen Zellen auf Polyester-Isocyanat-Basis
FR2080960A1 (fr) * 1970-02-05 1971-11-26 Bayer Ag
FR2085965A1 (fr) * 1970-04-09 1971-12-31 Dow Chemical Co

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1996006873A1 (fr) * 1994-08-31 1996-03-07 Smith & Nephew Plc Catalyseurs integres par liaison chimique
WO1997010275A1 (fr) * 1995-09-13 1997-03-20 Smith & Nephew Plc Compositions durcissables
AU711469B2 (en) * 1995-09-13 1999-10-14 Bsn Medical, Inc. Curable compositions
US6353077B2 (en) * 1995-09-13 2002-03-05 Michael Francis Shelvey Curable compositions
CN1100076C (zh) * 1995-09-13 2003-01-29 史密夫及内修公开有限公司 可固化组合物
US6756467B2 (en) * 1995-09-13 2004-06-29 Bsn Medical, Inc. Curable compositions
US6762274B2 (en) 2000-02-10 2004-07-13 Dow Global Technologies Inc. Low emission polyurethane polymers made with autocatalytic polyols
KR100850128B1 (ko) 2000-11-10 2008-08-04 제너럴 일렉트릭 캄파니 폴리우레탄 발포체의 성능을 개선시키는 방법
WO2002048229A2 (fr) * 2000-11-10 2002-06-20 Crompton Corporation Procede pour ameliorer les performances d'une mousse de polyurethanne
WO2002048229A3 (fr) * 2000-11-10 2002-12-27 Crompton Corp Procede pour ameliorer les performances d'une mousse de polyurethanne
CN1478111B (zh) * 2000-11-10 2012-10-17 通用电气公司 改进聚氨酯泡沫体性能的方法
CN100509901C (zh) * 2000-11-10 2009-07-08 通用电气公司 改进聚氨酯泡沫体性能的方法
US6387972B1 (en) 2001-02-15 2002-05-14 Crompton Corporation Process to enhance polyurethane foam performance
US7361695B2 (en) 2001-08-15 2008-04-22 Dow Global Technologies Inc. Process to manufacture flexible polyurethane foams
US6924321B2 (en) 2001-08-16 2005-08-02 Dow Global Technologies Inc. Polyols with autocatalytic characteristics and polyurethane products made therefrom
US6818675B2 (en) 2002-08-06 2004-11-16 General Electric Company Process for preparing polyurethane foam
EP3190133A1 (fr) 2005-11-14 2017-07-12 Dow Global Technologies Llc Procede de moulage de mousses polyurethane rigides avec une meilleure conductivite thermique

Also Published As

Publication number Publication date
GB9215488D0 (en) 1992-09-02
AU4568793A (en) 1994-02-14

Similar Documents

Publication Publication Date Title
EP1878492B2 (fr) N,N,N'-triméthyl-bis-(aminoéthyl) éther et ses dérivés en tant que catalyseurs pour polyuréthanes
EP1534766B1 (fr) Procede pour preparer une mousse de polyurethanne
JP3168457B2 (ja) ポリウレタン製造のためのｎ，ｎ，ｎ′−トリメチルビス（アミノエチル）エーテル置換尿素組成物
KR0141440B1 (ko) 폴리우레탄 폼을 제조하기 위한 제한된 활성 촉매로서의 4차 암모늄 카르복실레이트 분자내염 조성물
JPH07233234A (ja) ポリウレタン・フォームの製造方法の改良
EP1249461A2 (fr) Catalyseur amine bloqué par un acide pour la préparation de polyurethanes
JPH10324728A (ja) 水発泡ポリウレタンフォームの性能を改善するための反応性触媒組成物
EP1714989A1 (fr) Mousses de polyuréthane, fabriquées à partir de compositions de catalyseurs favorisant la formation de dioxyde de carbone et comportant des groupes hydroxyles primaires et une chaîne principale ethylène diamine.
EP1332167B1 (fr) Procede pour ameliorer les performances d'une mousse de polyurethane
KR970001537B1 (ko) 폴리우레탄 포움의 제조를 위한 3-퀴누클리디놀 촉매 조성물
EP0879837B1 (fr) Compositions de catalyseurs de polyuréthane pour améliorer la performance des mousses
US5288766A (en) Poyurea based dispersions, foams prepared therefrom, and a process for the preparation therein
JPH0343408A (ja) ウレタン触媒
EP1518872B1 (fr) Compositions de catalyseur de polyuréthane pour améliorer la performance de mousses rigides
US6156814A (en) Amido functional amine catalysts for the production of polyurethanes
WO1994002525A1 (fr) Amines a modification isocyanate utilisees a titre de catalyseurs pour la preparation de matieres polyurethanes
US5134217A (en) Use of n-(aminoalkyl) pyrrolidines as catalysts for the polyisocyanate polyaddition process
EP0877017B1 (fr) Composés de urée aminométhylpyrrolidine pour la préparation des polyuréthanes
EP0799821B1 (fr) Procédé de synthèse de polyuréthanes utilisant des catalyseurs aminés
US5194609A (en) 3-quinuclidinol catalyst compositions for making polyurethane foams
US6077877A (en) Reactive amine catalysts for use in polyurethane polymers
US6600001B1 (en) Alkylamino oxamides as low odor, non-fugitive catalysts for the production of polyurethanes
JP2885896B2 (ja) ウレタン発泡体用触媒
JP3994740B2 (ja) ポリウレタン樹脂を製造するためのイミダゾール触媒
EP1038894A2 (fr) Compositions de catalyseurs pour la préparation de polyuréthanes

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AU BR CA JP KR US

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): AT BE CH DE DK ES FR GB GR IE IT LU MC NL PT SE

DFPE Request for preliminary examination filed prior to expiration of 19th month from priority date (pct application filed before 20040101)
121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: CA

122 Ep: pct application non-entry in european phase