CA1109994A - Polyurethane catalyst - Google Patents
Polyurethane catalystInfo
- Publication number
- CA1109994A CA1109994A CA284,789A CA284789A CA1109994A CA 1109994 A CA1109994 A CA 1109994A CA 284789 A CA284789 A CA 284789A CA 1109994 A CA1109994 A CA 1109994A
- Authority
- CA
- Canada
- Prior art keywords
- catalyst
- polyol
- pdt
- urethane
- triamine
- 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
- 239000004814 polyurethane Substances 0.000 title abstract description 5
- 229920002635 polyurethane Polymers 0.000 title abstract description 5
- 239000003054 catalyst Substances 0.000 title description 22
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 150000003077 polyols Chemical class 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 13
- 229920005862 polyol Polymers 0.000 claims description 13
- 239000004604 Blowing Agent Substances 0.000 claims description 10
- 239000005056 polyisocyanate Substances 0.000 claims description 6
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims description 5
- 239000012975 dibutyltin dilaurate Substances 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 5
- 150000003606 tin compounds Chemical class 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 238000006116 polymerization reaction Methods 0.000 claims description 3
- 239000003426 co-catalyst Substances 0.000 claims description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims 1
- MUMVIYLVHVCYGI-UHFFFAOYSA-N n,n,n',n',n",n"-hexamethylmethanetriamine Chemical compound CN(C)C(N(C)C)N(C)C MUMVIYLVHVCYGI-UHFFFAOYSA-N 0.000 claims 1
- 239000011541 reaction mixture Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 abstract description 4
- 150000001875 compounds Chemical class 0.000 abstract description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 230000000694 effects Effects 0.000 abstract 1
- 239000000203 mixture Substances 0.000 description 14
- 239000006260 foam Substances 0.000 description 10
- 238000009472 formulation Methods 0.000 description 7
- 229920013701 VORANOL™ Polymers 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- -1 polyoxy propylene Polymers 0.000 description 5
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 229920001451 polypropylene glycol Polymers 0.000 description 3
- 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 3
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 3
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 2
- 239000000306 component Substances 0.000 description 2
- 239000000975 dye Substances 0.000 description 2
- 238000005187 foaming Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 235000019645 odor Nutrition 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 230000009257 reactivity Effects 0.000 description 2
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 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
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 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
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 229940052651 anticholinergic tertiary amines Drugs 0.000 description 1
- 125000003118 aryl group Chemical group 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- PNOXNTGLSKTMQO-UHFFFAOYSA-L diacetyloxytin Chemical compound CC(=O)O[Sn]OC(C)=O PNOXNTGLSKTMQO-UHFFFAOYSA-L 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
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000012974 tin catalyst Substances 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
- 150000003673 urethanes Chemical class 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
- 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
- C08G18/1808—Catalysts containing secondary or tertiary amines or salts thereof having alkylene polyamine groups
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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/725,229 US4080343A (en) | 1976-09-22 | 1976-09-22 | Polyurethane catalyst |
| US725,229 | 1976-09-22 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1109994A true CA1109994A (en) | 1981-09-29 |
Family
ID=24913695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA284,789A Expired CA1109994A (en) | 1976-09-22 | 1977-08-16 | Polyurethane catalyst |
Country Status (19)
| Country | Link |
|---|---|
| US (1) | US4080343A (en:Method) |
| JP (1) | JPS5339394A (en:Method) |
| AR (1) | AR218266A1 (en:Method) |
| AU (1) | AU504645B2 (en:Method) |
| BE (1) | BE858886A (en:Method) |
| BR (1) | BR7706207A (en:Method) |
| CA (1) | CA1109994A (en:Method) |
| DE (1) | DE2742510C3 (en:Method) |
| DK (1) | DK147975C (en:Method) |
| ES (1) | ES462526A1 (en:Method) |
| FR (1) | FR2365595B1 (en:Method) |
| GB (1) | GB1562160A (en:Method) |
| IT (1) | IT1085986B (en:Method) |
| MX (1) | MX147732A (en:Method) |
| NL (1) | NL183945C (en:Method) |
| NO (1) | NO146098C (en:Method) |
| NZ (1) | NZ184927A (en:Method) |
| SE (1) | SE437841B (en:Method) |
| ZA (1) | ZA774923B (en:Method) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2732292A1 (de) * | 1977-07-16 | 1979-02-01 | Bayer Ag | Verfahren zur herstellung von polyurethankunststoffen |
| DE2854384A1 (de) * | 1978-12-16 | 1980-07-03 | Bayer Ag | Verfahren zur herstellung von polyurethan-kunststoffen |
| CA1311478C (en) * | 1985-03-11 | 1992-12-15 | Edward A. Galla | Quaternary compounds for delayed action/enhanced curing catalysis inpolyurethane systems |
| US4707501A (en) * | 1987-02-13 | 1987-11-17 | Air Products And Chemicals, Inc. | Polyurethane foam catalysts that eliminate polyurea-containing polyol based masterbatch cure drift |
| US5039713A (en) * | 1991-02-07 | 1991-08-13 | Air Products And Chemicals, Inc. | Blowing reaction catalyst composition that provides cell opening of the resulting polyurethane foam |
| US5382602A (en) * | 1993-06-09 | 1995-01-17 | Duffy; Robert D. | Flexible slabstock polyurethane foam formulation for a rapid-cool process |
Family Cites Families (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1203948B (de) * | 1961-03-09 | 1965-10-28 | Bayer Ag | Verfahren zur Herstellung von Urethangruppen enthaltenden Schaumstoffen |
| NL283697A (en:Method) * | 1961-09-27 | |||
| BE624505A (en:Method) * | 1961-11-09 | |||
| DE1237777B (de) * | 1962-03-05 | 1967-03-30 | Kao Corp | Einstufiges Verfahren zur Herstellung von Polyurethanschaumstoffen |
| DE1694142C3 (de) * | 1967-03-25 | 1975-10-23 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Schaumstoffen |
| DE2029293C3 (de) * | 1970-06-13 | 1981-01-15 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanschaumstoffen Bayer AG, 5090 Leverkusen |
| DE2425448A1 (de) * | 1974-05-25 | 1975-12-04 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| DE2427273C2 (de) * | 1974-06-06 | 1982-10-07 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von formverschäumten Schaumstoffen mit selbsttrennenden Eigenschaften |
| FR2276333A1 (fr) * | 1974-06-28 | 1976-01-23 | Rhone Poulenc Ind | Procede de preparation de polyurethannes en presence de bis(dimethylaminohexyl-6)methylamine |
| GB1561618A (en) * | 1976-10-18 | 1980-02-27 | Texaco Development Corp | Polyurethane formation using high tertiary amine content catalysts |
-
1976
- 1976-09-22 US US05/725,229 patent/US4080343A/en not_active Expired - Lifetime
-
1977
- 1977-08-15 ZA ZA00774923A patent/ZA774923B/xx unknown
- 1977-08-16 MX MX170258A patent/MX147732A/es unknown
- 1977-08-16 NZ NZ184927A patent/NZ184927A/xx unknown
- 1977-08-16 CA CA284,789A patent/CA1109994A/en not_active Expired
- 1977-08-19 AU AU28046/77A patent/AU504645B2/en not_active Expired
- 1977-09-13 NL NLAANVRAGE7710030,A patent/NL183945C/xx not_active IP Right Cessation
- 1977-09-13 AR AR269175A patent/AR218266A1/es active
- 1977-09-16 BR BR7706207A patent/BR7706207A/pt unknown
- 1977-09-16 SE SE7710417A patent/SE437841B/xx not_active IP Right Cessation
- 1977-09-20 JP JP11227777A patent/JPS5339394A/ja active Granted
- 1977-09-20 IT IT27731/77A patent/IT1085986B/it active
- 1977-09-20 BE BE181063A patent/BE858886A/xx not_active IP Right Cessation
- 1977-09-21 DK DK417477A patent/DK147975C/da active
- 1977-09-21 ES ES462526A patent/ES462526A1/es not_active Expired
- 1977-09-21 NO NO773241A patent/NO146098C/no unknown
- 1977-09-21 GB GB39383/77A patent/GB1562160A/en not_active Expired
- 1977-09-21 FR FR7728487A patent/FR2365595B1/fr not_active Expired
- 1977-09-21 DE DE2742510A patent/DE2742510C3/de not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| DK147975C (da) | 1985-06-24 |
| NO146098C (no) | 1982-07-28 |
| US4080343A (en) | 1978-03-21 |
| FR2365595A1 (fr) | 1978-04-21 |
| NO146098B (no) | 1982-04-19 |
| IT1085986B (it) | 1985-05-28 |
| SE437841B (sv) | 1985-03-18 |
| NZ184927A (en) | 1978-11-13 |
| ZA774923B (en) | 1978-06-28 |
| JPS5339394A (en) | 1978-04-11 |
| AR218266A1 (es) | 1980-05-30 |
| MX147732A (es) | 1983-01-10 |
| DE2742510B2 (de) | 1980-01-03 |
| DE2742510A1 (de) | 1978-03-23 |
| FR2365595B1 (fr) | 1986-03-28 |
| DK417477A (da) | 1978-03-23 |
| NL183945C (nl) | 1989-03-01 |
| NL183945B (nl) | 1988-10-03 |
| AU2804677A (en) | 1979-02-22 |
| SE7710417L (sv) | 1978-03-23 |
| AU504645B2 (en) | 1979-10-18 |
| GB1562160A (en) | 1980-03-05 |
| DE2742510C3 (de) | 1986-11-13 |
| NL7710030A (nl) | 1978-03-28 |
| JPS5337399B2 (en:Method) | 1978-10-07 |
| NO773241L (no) | 1978-03-28 |
| ES462526A1 (es) | 1978-07-01 |
| BE858886A (fr) | 1978-03-20 |
| DK147975B (da) | 1985-01-21 |
| BR7706207A (pt) | 1978-05-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MKEX | Expiry |