EP1551909A1 - Katalysatorkombinationen zur erh hung des trimergehalts in schaumstoff - Google Patents
Katalysatorkombinationen zur erh hung des trimergehalts in schaumstoffInfo
- 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- Withdrawn
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)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2002/022807 WO2004009687A1 (en) | 2002-07-18 | 2002-07-18 | Catalyst combinations for increasing trimer content in foam |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1551909A1 true EP1551909A1 (de) | 2005-07-13 |
| EP1551909A4 EP1551909A4 (de) | 2007-12-26 |
Family
ID=30769016
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP02744874A Withdrawn EP1551909A4 (de) | 2002-07-18 | 2002-07-18 | Katalysatorkombinationen zur erh hung des trimergehalts in schaumstoff |
Country Status (5)
| Country | Link |
|---|---|
| EP (1) | EP1551909A4 (de) |
| CN (1) | CN1639240A (de) |
| AU (1) | AU2002346113A1 (de) |
| CA (1) | CA2493404A1 (de) |
| WO (1) | WO2004009687A1 (de) |
Families Citing this family (7)
| 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)
| 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 |
-
2002
- 2002-07-18 CN CNA028293312A patent/CN1639240A/zh active Pending
- 2002-07-18 WO PCT/US2002/022807 patent/WO2004009687A1/en not_active Ceased
- 2002-07-18 AU AU2002346113A patent/AU2002346113A1/en not_active Abandoned
- 2002-07-18 EP EP02744874A patent/EP1551909A4/de not_active Withdrawn
- 2002-07-18 CA CA002493404A patent/CA2493404A1/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| CN1639240A (zh) | 2005-07-13 |
| EP1551909A4 (de) | 2007-12-26 |
| CA2493404A1 (en) | 2004-01-29 |
| WO2004009687A1 (en) | 2004-01-29 |
| AU2002346113A1 (en) | 2004-02-09 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| 17P | Request for examination filed |
Effective date: 20050111 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AT BE BG CH CY CZ DE DK EE ES FI FR GB GR IE IT LI LU MC NL PT SE SK TR |
|
| AX | Request for extension of the european patent |
Extension state: AL LT LV MK RO SI |
|
| DAX | Request for extension of the european patent (deleted) | ||
| A4 | Supplementary search report drawn up and despatched |
Effective date: 20071128 |
|
| RIC1 | Information provided on ipc code assigned before grant |
Ipc: C08G 18/00 20060101ALI20071119BHEP Ipc: B01J 31/00 20060101ALI20071119BHEP Ipc: C08J 9/00 20060101AFI20040210BHEP |
|
| RAP1 | Party data changed (applicant data changed or rights of an application transferred) |
Owner name: HUNTSMAN PETROCHEMICAL LLC |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE APPLICATION IS DEEMED TO BE WITHDRAWN |
|
| 18D | Application deemed to be withdrawn |
Effective date: 20100202 |