DE2420774C2 - Quartärer Hydroxyalkylammoniumphenolat-Katalysator zur Herstellung von Polyurethan- und Polyurethan-Polyisocyanurat-Schäumen - Google Patents
Quartärer Hydroxyalkylammoniumphenolat-Katalysator zur Herstellung von Polyurethan- und Polyurethan-Polyisocyanurat-SchäumenInfo
- Publication number
- DE2420774C2 DE2420774C2 DE19742420774 DE2420774A DE2420774C2 DE 2420774 C2 DE2420774 C2 DE 2420774C2 DE 19742420774 DE19742420774 DE 19742420774 DE 2420774 A DE2420774 A DE 2420774A DE 2420774 C2 DE2420774 C2 DE 2420774C2
- Authority
- DE
- Germany
- Prior art keywords
- polyurethane
- catalyst
- udf54
- udf53
- quaternary
- 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.)
- Expired
Links
- 239000003054 catalyst Substances 0.000 title claims description 40
- 239000006260 foam Substances 0.000 title claims description 10
- ISWSIDIOOBJBQZ-UHFFFAOYSA-M phenolate Chemical compound [O-]C1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-M 0.000 title claims description 9
- 229940031826 phenolate Drugs 0.000 title claims description 9
- 229920000582 polyisocyanurate Polymers 0.000 title claims description 7
- 239000011495 polyisocyanurate Substances 0.000 title claims description 7
- 229920002635 polyurethane Polymers 0.000 title claims description 7
- 239000004814 polyurethane Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 6
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 claims description 7
- 229960002887 deanol Drugs 0.000 claims description 7
- 239000012972 dimethylethanolamine Substances 0.000 claims description 7
- 150000003512 tertiary amines Chemical class 0.000 claims description 7
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 4
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 239000002904 solvent Substances 0.000 claims description 3
- ZUHBJQKHDGXUFS-UHFFFAOYSA-N 1-amino-2-methylicos-3-en-2-ol Chemical compound CC(O)(CN)C=CCCCCCCCCCCCCCCCC ZUHBJQKHDGXUFS-UHFFFAOYSA-N 0.000 claims 1
- JSAVNAHQPCVCQJ-UHFFFAOYSA-N 1-amino-2-methylicosan-2-ol Chemical compound CC(O)(CN)CCCCCCCCCCCCCCCCCC JSAVNAHQPCVCQJ-UHFFFAOYSA-N 0.000 claims 1
- LUPIFLARJQGECT-UHFFFAOYSA-N 1-amino-4-phenylbutan-2-ol Chemical compound NCC(O)CCC1=CC=CC=C1 LUPIFLARJQGECT-UHFFFAOYSA-N 0.000 claims 1
- NDLNTMNRNCENRZ-UHFFFAOYSA-N 2-[2-hydroxyethyl(octadecyl)amino]ethanol Chemical compound CCCCCCCCCCCCCCCCCCN(CCO)CCO NDLNTMNRNCENRZ-UHFFFAOYSA-N 0.000 claims 1
- MIZIOHLLYXVEHJ-UHFFFAOYSA-N 2-[benzyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)CC1=CC=CC=C1 MIZIOHLLYXVEHJ-UHFFFAOYSA-N 0.000 claims 1
- GVNHOISKXMSMPX-UHFFFAOYSA-N 2-[butyl(2-hydroxyethyl)amino]ethanol Chemical compound CCCCN(CCO)CCO GVNHOISKXMSMPX-UHFFFAOYSA-N 0.000 claims 1
- HHPDFYDITNAMAM-UHFFFAOYSA-N 2-[cyclohexyl(2-hydroxyethyl)amino]ethanol Chemical compound OCCN(CCO)C1CCCCC1 HHPDFYDITNAMAM-UHFFFAOYSA-N 0.000 claims 1
- BFSVOASYOCHEOV-UHFFFAOYSA-N 2-diethylaminoethanol Chemical compound CCN(CC)CCO BFSVOASYOCHEOV-UHFFFAOYSA-N 0.000 claims 1
- AKNUHUCEWALCOI-UHFFFAOYSA-N N-ethyldiethanolamine Chemical compound OCCN(CC)CCO AKNUHUCEWALCOI-UHFFFAOYSA-N 0.000 claims 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 claims 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 claims 1
- 230000000694 effects Effects 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- 230000000052 comparative effect Effects 0.000 description 5
- 230000032683 aging Effects 0.000 description 4
- 239000002243 precursor Substances 0.000 description 4
- -1 N,N-dimethyl-N-2-hydroxyethyl-N-2-hydroxypropyl ammonium phenolate Chemical compound 0.000 description 3
- 150000001412 amines Chemical group 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- 125000002947 alkylene group Chemical group 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 239000012973 diazabicyclooctane Substances 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 1
- 239000004604 Blowing Agent Substances 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical class NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- AFYPFACVUDMOHA-UHFFFAOYSA-N chlorotrifluoromethane Chemical compound FC(F)(F)Cl AFYPFACVUDMOHA-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-M hydroxide Chemical compound [OH-] XLYOFNOQVPJJNP-UHFFFAOYSA-M 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920006389 polyphenyl polymer Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- 229940029284 trichlorofluoromethane Drugs 0.000 description 1
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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/04—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers only
- C08G65/06—Cyclic ethers having no atoms other than carbon and hydrogen outside the ring
- C08G65/08—Saturated oxiranes
- C08G65/10—Saturated oxiranes characterised by the catalysts used
- C08G65/105—Onium compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/04—Methanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/08—Ethanol
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C31/00—Saturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C31/02—Monohydroxylic acyclic alcohols
- C07C31/10—Monohydroxylic acyclic alcohols containing three carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C33/00—Unsaturated compounds having hydroxy or O-metal groups bound to acyclic carbon atoms
- C07C33/18—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part
- C07C33/20—Monohydroxylic alcohols containing only six-membered aromatic rings as cyclic part monocyclic
- C07C33/22—Benzylalcohol; phenethyl alcohol
-
- 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
- C08G18/1875—Catalysts containing secondary or tertiary amines or salts thereof containing ammonium salts or mixtures of secondary of tertiary amines and 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
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2642—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds characterised by the catalyst used
- C08G65/2669—Non-metals or compounds thereof
- C08G65/2672—Nitrogen or compounds thereof
-
- 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
- C08G8/00—Condensation polymers of aldehydes or ketones with phenols only
- C08G8/04—Condensation polymers of aldehydes or ketones with phenols only of aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US37744673A | 1973-07-09 | 1973-07-09 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2420774A1 DE2420774A1 (de) | 1975-01-30 |
| DE2420774C2 true DE2420774C2 (de) | 1987-05-14 |
Family
ID=23489142
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19742420774 Expired DE2420774C2 (de) | 1973-07-09 | 1974-04-29 | Quartärer Hydroxyalkylammoniumphenolat-Katalysator zur Herstellung von Polyurethan- und Polyurethan-Polyisocyanurat-Schäumen |
Country Status (8)
| Country | Link |
|---|---|
| JP (1) | JPS5946938B2 (enrdf_load_stackoverflow) |
| BE (1) | BE814850A (enrdf_load_stackoverflow) |
| CA (1) | CA1029899A (enrdf_load_stackoverflow) |
| DE (1) | DE2420774C2 (enrdf_load_stackoverflow) |
| FR (1) | FR2236841B1 (enrdf_load_stackoverflow) |
| GB (1) | GB1465812A (enrdf_load_stackoverflow) |
| IT (1) | IT1009906B (enrdf_load_stackoverflow) |
| NL (1) | NL179294C (enrdf_load_stackoverflow) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS545425B2 (enrdf_load_stackoverflow) * | 1973-11-07 | 1979-03-16 | ||
| DE2806731A1 (de) | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
| JPS5921653A (ja) * | 1982-07-05 | 1984-02-03 | ビ−エ−エス エフ アクチエンゲゼルシヤフト | 第四アンモニウム塩の製造方法 |
| JPS61163248U (enrdf_load_stackoverflow) * | 1985-03-30 | 1986-10-09 | ||
| WO2006098251A1 (ja) | 2005-03-15 | 2006-09-21 | Polyplastics Co., Ltd. | 不安定末端基分解処理剤、それを用いた安定化ポリアセタール樹脂、製造方法、組成物及び成形体 |
| US20090176907A1 (en) | 2008-01-08 | 2009-07-09 | Ramesh Subramanian | Direct-to-metal radiation curable compositions |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| BE539515A (enrdf_load_stackoverflow) * | ||||
| US2689833A (en) * | 1951-09-21 | 1954-09-21 | Rohm & Haas | Resinous quaternary ammonium alkoxides |
| US3010963A (en) * | 1959-05-21 | 1961-11-28 | Houdry Process Corp | Quaternary hydroxyalkyl tertiary heterocyclic amine bases and salts |
| CH480788A (de) * | 1967-10-16 | 1969-12-31 | Ciba Geigy | Verwendung eines quaternären Ammonium-Pentachlorphenolates zum antimikrobiellen Ausrüsten bzw. zum Schützen von textilem Material gegen schädliche Mirkoorganismen |
-
1974
- 1974-04-01 CA CA196,440A patent/CA1029899A/en not_active Expired
- 1974-04-10 NL NL7404934A patent/NL179294C/xx not_active IP Right Cessation
- 1974-04-10 GB GB1596874A patent/GB1465812A/en not_active Expired
- 1974-04-18 IT IT2159474A patent/IT1009906B/it active
- 1974-04-24 JP JP49046397A patent/JPS5946938B2/ja not_active Expired
- 1974-04-29 DE DE19742420774 patent/DE2420774C2/de not_active Expired
- 1974-05-09 FR FR7416052A patent/FR2236841B1/fr not_active Expired
- 1974-05-10 BE BE144171A patent/BE814850A/xx not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| CA1029899A (en) | 1978-04-18 |
| FR2236841B1 (enrdf_load_stackoverflow) | 1977-10-21 |
| BE814850A (fr) | 1974-09-02 |
| NL7404934A (nl) | 1975-01-13 |
| JPS5946938B2 (ja) | 1984-11-15 |
| DE2420774A1 (de) | 1975-01-30 |
| IT1009906B (it) | 1976-12-20 |
| FR2236841A1 (enrdf_load_stackoverflow) | 1975-02-07 |
| GB1465812A (en) | 1977-03-02 |
| NL179294B (nl) | 1986-03-17 |
| JPS5025510A (enrdf_load_stackoverflow) | 1975-03-18 |
| NL179294C (nl) | 1986-08-18 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |