EP1551909A1 - Combinaison de catalyseurs pour ameliorer le contenu de trimeres dans une mousse - Google Patents

Combinaison de catalyseurs pour ameliorer le contenu de trimeres dans une mousse

Info

Publication number
EP1551909A1
EP1551909A1 EP02744874A EP02744874A EP1551909A1 EP 1551909 A1 EP1551909 A1 EP 1551909A1 EP 02744874 A EP02744874 A EP 02744874A EP 02744874 A EP02744874 A EP 02744874A EP 1551909 A1 EP1551909 A1 EP 1551909A1
Authority
EP
European Patent Office
Prior art keywords
catalyst
foam
group
isocyanate
trimer
Prior art date
Legal status (The legal status 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 status listed.)
Withdrawn
Application number
EP02744874A
Other languages
German (de)
English (en)
Other versions
EP1551909A4 (fr
Inventor
Robert A. Grigsby, Jr.
Robert L. Zimmerman
Ernest L. Rister, Jr.
Pierre Gilbert Henri Jean Chaffanjon
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Huntsman Petrochemical LLC
Original Assignee
Huntsman Specialty Chemicals Corp
Huntsman Petrochemical LLC
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 Huntsman Specialty Chemicals Corp, Huntsman Petrochemical LLC filed Critical Huntsman Specialty Chemicals Corp
Publication of EP1551909A1 publication Critical patent/EP1551909A1/fr
Publication of EP1551909A4 publication Critical patent/EP1551909A4/fr
Withdrawn legal-status Critical Current

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
    • C08G18/1825—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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/08—Processes
    • C08G18/09—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture
    • C08G18/092—Processes comprising oligomerisation of isocyanates or isothiocyanates involving reaction of a part of the isocyanate or isothiocyanate groups with each other in the reaction mixture oligomerisation to isocyanurate 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
    • C08G18/08—Processes
    • C08G18/16—Catalysts
    • C08G18/161—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22
    • C08G18/163—Catalysts containing two or more components to be covered by at least two of the groups C08G18/166, C08G18/18 or C08G18/22 covered by C08G18/18 and C08G18/22
    • 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
    • C08G18/225—Catalysts containing metal compounds of alkali or alkaline earth metals
    • 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
    • C08G2110/0025—Foam properties 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
    • C08G2110/0083—Foam properties prepared using water as the sole blowing agent

Definitions

  • This invention relates to catalyst combinations useful in the manufacture of
  • polyurethane-based foam products More particularly it relates to catalyst
  • foam products to promote the reaction between an isocyanate group in one or more
  • ethanolamine is available from Huntsman Petrochemical Corporation of Austin, Texas
  • JEFFCAT® Z- 110 under the tradename of JEFFCAT® Z- 110, and has the structure:
  • trimer groups present and form a trimer, for example the trimer of MDI.
  • the trimer of MDI for example the trimer of MDI.
  • this material is used as a "blowing catalyst" in a foam, and as such is employed primarily to enhance the foam
  • trimer groups in a foam should improve the burn properties of an isocyanurate foam.
  • one of the components does not itself promote trimer formation to a large extent.
  • the present invention provides a catalyst combination useful in the formation
  • an amine component that comprises N,N,N'-trimethylaminoethyl-
  • the invention also provides a process
  • an amine component comprising N,N,N'-trimethylaminoethyl-
  • FIG. 1 is a graphical representation of the trimer content in a plurality of foam-
  • FIG. 2 is a graphical representation of the increase in trimer content during the course
  • FIG. 3 is a graphical representation of the decrease in isocyanate content during the
  • FIG. 4A is a graphical representation of the increase in trimer content during the
  • FIG. 4B is a graphical representation of the increase in trimer content during the
  • FIG. 4C is a graphical representation of the increase in trimer content during the
  • FIG. 5A is a graphical representation of the decrease in isocyanate content during the
  • FIG. 5B is a graphical representation of the decrease in isocyanate content during the
  • FIG. 5C is a graphical representation of the decrease in isocyanate content during the
  • the present invention employs JEFFCAT® Z-l 10 with at least one
  • JEFFCAT® Z-l 10 can be used in combination with
  • blowing agents can also be present in the formulation, as the use of such
  • blowing agents is known to those skilled in the art, such as: non-CFC-containing
  • blowing agents water, HCFC's and CFC-containing blowing agents, with the
  • pentanes including: n-pentane, cyclopentane, neopentane, isopentane, and mixtures
  • blowing agent being especially-preferred as blowing agent.
  • the heated probe was started at room temperature, and
  • foam formulations were made and poured in identical fashion, except for the catalyst
  • base polyol, B-component was made by combining: 100 parts by weight (“pbw”) STEPHANOL® PS-2352 with 20 pbw EXXSOL® 1600, 2.5 pbw B-8477, and 0.5
  • B-8477 is a modified siloxane material sold by Goldschmidt AG of
  • the catalyst was added to the base polyol and mixed until homogeneous.
  • isocyanate-derived foam is expressed as the ratio of the number of isocyanate groups to
  • a master polyol blend was made using the following amounts of the specified
  • Catalyst A Catalyst B
  • “Cream Time” is the amount of time elapsed between initial mixing of the
  • the foam was mixed for seven seconds, and then poured on top of the
  • JEFFCAT® Z-l 10 makes more effective utilization of the isocyanate in the foam than
  • JEFFCAT® Z-l 10 significantly increases the trimer content of a foam, and increases the
  • EXXOL®1600 available from Exxon Chemical Corp., and which contains a mixture of
  • PIR polyisocyanurate
  • catalyst combination according to the invention may be employed can consist of any
  • RUBINATE® M RUBINATE ® 1850 RUBINATE®
  • Aromatic polyisocyanates such as toluene diisocyanate, diphenylmethane-4,4'-
  • polymeric MDI and the like aliphatic polyisocyanates such as
  • hexamethylenediisocyanate and the like hexamethylenediisocyanate and the like; alicyclic polyisocyanates such a
  • denatured isocyanate such as carbodiimide denatured substances
  • polyisocyanates thereof may include
  • aliphatic isocyanates of the type described in U.S. Pat. No. 4,748,192. These include
  • aliphatic diisocyanates and, more particularly, are the trimerized or the biuretic form
  • an aliphatic diisocyanate such as hexamethylene diisocyanate, or the bifunctional
  • Cyclohexane diisocyanate is also to be considered a useful aliphatic
  • isocyanate isocyanate.
  • Other useful aliphatic polyisocyanates are described in U.S. Pat. No.
  • 1,4-tetramethylene diisocyanate are also useful.
  • cycloaliphatic diisocyanates are also useful.
  • JEFFCAT® TAP JEFFCAT®
  • JEFFCAT® PM JEFFCAT® M-75, JEFFCAT® MM-20, JEFFCAT® MM-27,
  • TMR®2, TMR®3, TMR®4 or any material that is known to those skilled in the art as
  • TMR® is a registered trademark of Air Products and Chemicals, Inc., of Allentown,
  • Polyols useful in providing a foam according to the present invention include
  • aromatic polyesterpolyols amino polyols, mannich polyols, sucrose-derived polyols,
  • Polyetherpolyols include, for example,
  • polyhydric alcohols such as glycols, glycerin, pentaerythritol, and sucrose; aliphatic
  • amine compounds such as ammonia, and ethyleneamine; aromatic amine compounds
  • Polymer polyol is exemplified by a reaction product of said
  • polyetherpolyol with ethylenic unsaturated monomer such as butadiene, acrylonitrile
  • Polyesterpolyols include those which are produced from a dibasic acid and a
  • polyhydric alcohol such as, for example, polyethyleneadipate and
  • polyethyleneterephthalates which may include those products reclaimed from waste
  • Blowing agents useful in accordance with the present invention are:
  • low boiling point hydrocarbons such as pentane, halogenated
  • halogenated ethanes may be used as halogenated hydrocarbons.
  • halogenated hydrocarbons Among them,
  • chlorofluorocarbon compounds such as trichloromonofluoromethane (R-l l), dichlorotrifluoroethane (R-123), dichloromonofluoroethane (R-141b), R-
  • the amount of the foaming agent to be used is
  • the stabilizer is selected, for example, from non-ionic
  • surfactants such as organopolysiloxanepolyoxyalkylene copolymers, silicone-glycol
  • the amount of the stabilizer is not
  • invention may be flexible foam, HR foam, semi-rigid foam, rigid foam, microcellular
  • foaming agent which is processed in a combined form such as foil, coating, or border
  • resins such as polyvinylchloride resin, ABS resin, polycarbonate resin, and the like, metals, glasses, and the like.
  • articles of automobiles such as instrument panels, seats, head rests, arm rests, and
  • weight values include both the JEFFCAT® Z-l 10 catalyst and any other amine
  • organic carboxylic acid salts thereof and organo tin compounds which are usually
  • auxiliary catalysts used as co-catalysts may be employed as auxiliary catalysts.
  • trimer catalyst present in a composition from which a foam
  • trimer structure as such trimer structure is known to those skilled in the art as isocyanurates.
  • Trimer catalysts include alkali salts of an carboxylic acids, such as sodium,
  • trimer groups react with one another to form an isocyanurate structure.
  • catalysts include potassium octoate and potassium acetate.
  • certain amines may also function as trimer catalysts, some of which include: JEFFCAT® TR-52
  • TMR2® TMR3 which are available from Air Products and Chemicals, Inc.
  • Then it may be produced is any temperature in the range from about 25°C to about 200°C.
  • psi pound per square inch

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

L'invention concerne des compositions utilisées en tant que catalyseurs dans la production de mousse en polyisocyanurate. Les compositions de l'invention comprennent de la N, N, N'-triméthylaminoéthyl-éthanolamine en combinaison avec un autre catalyseur utilisé dans la réalisation de la trimérisation d'isocyanates. Lors de la réalisation de la trimérisation, le contenu isocyanate de la mousse diminue ce qui permet d'obtenir une mousse présentant de meilleures propriétés de combustion que la technique antérieure. La diminution du contenu isocyanate d'une mousse peut également permettre le démoulage plus rapide d'une mousse moulée, grâce à une adhésivité réduite.
EP02744874A 2002-07-18 2002-07-18 Combinaison de catalyseurs pour ameliorer le contenu de trimeres dans une mousse Withdrawn EP1551909A4 (fr)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
PCT/US2002/022807 WO2004009687A1 (fr) 2002-07-18 2002-07-18 Combinaison de catalyseurs pour ameliorer le contenu de trimeres dans une mousse

Publications (2)

Publication Number Publication Date
EP1551909A1 true EP1551909A1 (fr) 2005-07-13
EP1551909A4 EP1551909A4 (fr) 2007-12-26

Family

ID=30769016

Family Applications (1)

Application Number Title Priority Date Filing Date
EP02744874A Withdrawn EP1551909A4 (fr) 2002-07-18 2002-07-18 Combinaison de catalyseurs pour ameliorer le contenu de trimeres dans une mousse

Country Status (5)

Country Link
EP (1) EP1551909A4 (fr)
CN (1) CN1639240A (fr)
AU (1) AU2002346113A1 (fr)
CA (1) CA2493404A1 (fr)
WO (1) WO2004009687A1 (fr)

Families Citing this family (7)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102005034052A1 (de) * 2005-07-21 2007-01-25 Goldschmidt Gmbh Trimerisierungskatalysatoren
DE102005041763A1 (de) * 2005-09-01 2007-03-08 Basf Ag Polyisocyanurat Hartschaum und Verfahren zur Herstellung
CN101501092B (zh) * 2006-08-11 2011-09-28 东曹株式会社 用于制备聚氨酯树脂的催化剂组合物以及聚氨酯树脂的制备方法
US7872055B2 (en) 2008-12-11 2011-01-18 Air Products and Chenicals, Inc. Catalyst composition for water blown, low density, rigid polyurethane foam
CN102432813B (zh) * 2011-03-21 2014-04-30 江苏科泰绝热新材料有限公司 一种用离子液体催化制备pir材料的方法
US12157790B2 (en) 2019-01-22 2024-12-03 Covestro Intellectual Property Gmbh & Co. Kg Composite materials based on dual-cure urethane polymers and dual-cure isocyanurate polymers
CN110172132A (zh) * 2019-05-31 2019-08-27 绵阳彩馥兰科技有限责任公司 一种复合催化剂

Family Cites Families (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4217247A (en) * 1979-03-07 1980-08-12 Mobay Chemical Corporation Catalyst system for polyurethane foams
US4349638A (en) * 1981-11-02 1982-09-14 Basf Wyandotte Corporation Process for the preparation of foams characterized by isocyanurate, and/or urethane linkages involving the use of alkali metal ammonium carboxylate catalysts
DD236745A1 (de) * 1984-04-11 1986-06-18 Univ Dresden Tech Verfahren zur polymerisation von isocyanaten (iv)
GB8531180D0 (en) * 1985-12-18 1986-01-29 Ici Plc Cocatalyst systems
US4710521A (en) * 1986-07-25 1987-12-01 The Celotex Corporation Catalyst mixtures for polyisocyanurate foam
US5248646A (en) * 1991-09-20 1993-09-28 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5162379A (en) * 1991-09-20 1992-11-10 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5086081A (en) * 1991-09-20 1992-02-04 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5166223A (en) * 1991-09-20 1992-11-24 Air Products And Chemicals, Inc. Hydroxyl group-containing amine-boron adducts are reduced odor catalyst compositions for the production of polyurethanes
US5238894A (en) * 1991-09-20 1993-08-24 Air Products And Chemcials, Inc. Hydroxyl group-containing amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5177046A (en) * 1991-09-20 1993-01-05 Air Products And Chemicals, Inc. Amine-boron adducts as reduced odor catalyst compositions for the production of polyurethanes
US5454561A (en) * 1994-05-20 1995-10-03 Smith; Christopher L. Tethered baseball batting practice apparatus

Also Published As

Publication number Publication date
CN1639240A (zh) 2005-07-13
EP1551909A4 (fr) 2007-12-26
CA2493404A1 (fr) 2004-01-29
WO2004009687A1 (fr) 2004-01-29
AU2002346113A1 (en) 2004-02-09

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