DE1071329B - Ver fahren zur Herstellung von Polyurethan-Schaumstoffen - Google Patents
Ver fahren zur Herstellung von Polyurethan-SchaumstoffenInfo
- Publication number
- DE1071329B DE1071329B DENDAT1071329D DE1071329DA DE1071329B DE 1071329 B DE1071329 B DE 1071329B DE NDAT1071329 D DENDAT1071329 D DE NDAT1071329D DE 1071329D A DE1071329D A DE 1071329DA DE 1071329 B DE1071329 B DE 1071329B
- Authority
- DE
- Germany
- Prior art keywords
- castor oil
- polyurethane foams
- reaction product
- production
- product
- 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.)
- Pending
Links
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 7
- 239000011496 polyurethane foam Substances 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title claims description 5
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 claims description 18
- 229920001228 polyisocyanate Polymers 0.000 claims description 15
- 239000005056 polyisocyanate Substances 0.000 claims description 15
- 238000000034 method Methods 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000000047 product Substances 0.000 claims description 10
- 239000004359 castor oil Substances 0.000 claims description 9
- 235000019438 castor oil Nutrition 0.000 claims description 9
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 claims description 9
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 6
- 239000003054 catalyst Substances 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 claims description 4
- 238000006068 polycondensation reaction Methods 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 239000002253 acid Substances 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- CKDWPUIZGOQOOM-UHFFFAOYSA-N Carbamyl chloride Chemical compound NC(Cl)=O CKDWPUIZGOQOOM-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims description 2
- 239000012948 isocyanate Substances 0.000 claims description 2
- 150000002513 isocyanates Chemical class 0.000 claims description 2
- 239000006260 foam Substances 0.000 description 10
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 6
- 239000000243 solution Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 238000002156 mixing Methods 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 229920000768 polyamine Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- -1 (2-diethylaminoethyl) - hexahydro-s-triazine Chemical compound 0.000 description 1
- UGYQLLBBRLDEHY-UHFFFAOYSA-N 2-(diethylamino)propanamide Chemical compound CCN(CC)C(C)C(N)=O UGYQLLBBRLDEHY-UHFFFAOYSA-N 0.000 description 1
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
- 240000004307 Citrus medica Species 0.000 description 1
- SVYKKECYCPFKGB-UHFFFAOYSA-N N,N-dimethylcyclohexylamine Chemical compound CN(C)C1CCCCC1 SVYKKECYCPFKGB-UHFFFAOYSA-N 0.000 description 1
- HTLZVHNRZJPSMI-UHFFFAOYSA-N N-ethylpiperidine Chemical compound CCN1CCCCC1 HTLZVHNRZJPSMI-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- VWPHTOATEPXMCB-UHFFFAOYSA-N carbamoyl chloride;hydrochloride Chemical compound Cl.NC(Cl)=O VWPHTOATEPXMCB-UHFFFAOYSA-N 0.000 description 1
- 239000001569 carbon dioxide Substances 0.000 description 1
- 229910002092 carbon dioxide Inorganic materials 0.000 description 1
- 210000005056 cell body Anatomy 0.000 description 1
- XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000000706 filtrate Substances 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 1
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 238000002329 infrared spectrum Methods 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 231100000252 nontoxic Toxicity 0.000 description 1
- 230000003000 nontoxic effect Effects 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N toluene Substances CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/74—Polyisocyanates or polyisothiocyanates cyclic
- C08G18/76—Polyisocyanates or polyisothiocyanates cyclic aromatic
- C08G18/7657—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings
- C08G18/7664—Polyisocyanates or polyisothiocyanates cyclic aromatic containing two or more aromatic rings containing alkylene polyphenyl 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/36—Hydroxylated esters of higher fatty 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
- C08G2110/00—Foam properties
- C08G2110/0016—Foam properties semi-rigid
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)
- Cosmetics (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB14899/57A GB848672A (en) | 1957-05-10 | 1957-05-10 | Manufacture of foamed polymeric materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1071329B true DE1071329B (de) | 1959-12-17 |
Family
ID=10049501
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DENDAT1071329D Pending DE1071329B (de) | 1957-05-10 | Ver fahren zur Herstellung von Polyurethan-Schaumstoffen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US2950263A (OSRAM) |
| BE (1) | BE567550A (OSRAM) |
| DE (1) | DE1071329B (OSRAM) |
| FR (1) | FR1200377A (OSRAM) |
| GB (1) | GB848672A (OSRAM) |
| NL (1) | NL280259A (OSRAM) |
Families Citing this family (45)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3163666A (en) * | 1964-12-29 | x j jxx | ||
| US3152162A (en) * | 1959-07-29 | 1964-10-06 | Bayer Ag | Polyisocyanate-carbodiimide adducts and process for the production thereof |
| NL133349C (OSRAM) * | 1963-12-30 | |||
| US3362979A (en) * | 1964-01-02 | 1968-01-09 | Jefferson Chem Co Inc | Mixtures of methylene-bridged polyphenyl polyisocyanates |
| DE1242623B (de) * | 1964-02-28 | 1967-06-22 | Kaiser Aluminium Chem Corp | Verfahren zur Herstellung von primaeren Polyaminen |
| US4071558A (en) * | 1967-09-28 | 1978-01-31 | Texaco Development Corporation | Aromatic polyamines and their preparation |
| US3676497A (en) * | 1968-08-06 | 1972-07-11 | Upjohn Co | Process for preparing di(aminophenyl)-methanes |
| US4221877A (en) * | 1978-01-27 | 1980-09-09 | Texaco Development Corp. | Modified diphenylmethane diisocyanates useful in polyurethanes or polyisocyanurates |
| US4254069A (en) * | 1979-04-30 | 1981-03-03 | Texaco Development Corp. | Heat stable reaction injection molded elastomers |
| US4469657A (en) * | 1980-02-08 | 1984-09-04 | Texaco Inc. | Rim elastomers with improved catalyst efficiency |
| US4444703A (en) * | 1980-09-10 | 1984-04-24 | Texaco Inc. | Reinforced reaction injection molded elastomers |
| US4381353A (en) * | 1981-11-02 | 1983-04-26 | Texaco Inc. | Sprayed polyurethane foams employing reactive amines to improve the foam surface |
| US4463050A (en) * | 1982-09-30 | 1984-07-31 | Texaco Inc. | Polyurethane catalyst system additive which permits the use of relatively "cold" molds |
| US4442238A (en) * | 1982-11-22 | 1984-04-10 | Texaco Inc. | Aromatic amide polyols for rigid polyurethane foams |
| US4760100A (en) * | 1987-10-26 | 1988-07-26 | Arco Chemical Company | Terephthalic ester polyols modified with ethoxylated amines and amides and rigid foams therefrom |
| US4785026A (en) * | 1987-11-24 | 1988-11-15 | Arco Chemical Company | Polymer polyols with high solids content |
| US5192812A (en) * | 1991-02-12 | 1993-03-09 | Union Carbide Chemicals & Plastics Technology Corporation | Cell openers for urethane foam surfactants |
| DE19916946C1 (de) | 1999-04-15 | 2000-07-27 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| DE19916945C1 (de) * | 1999-04-15 | 2000-10-05 | Clariant Gmbh | Aromatische Aldehydharze und ihre Verwendung als Emulsionsspalter |
| US6462109B1 (en) | 1999-10-12 | 2002-10-08 | Eastman Chemical Company | Surfactantless latex compositions and methods of making polymer blends using these compositions |
| US6844390B2 (en) * | 2001-04-09 | 2005-01-18 | Eastman Chemical Company | Modified alkyd compositions comprising polyol latex compositions and processes of making them |
| US20090005476A1 (en) * | 2001-04-09 | 2009-01-01 | Eastman Chemical Company | Polyol latex compositions and process of making them |
| US6699931B2 (en) | 2001-04-09 | 2004-03-02 | Eastman Chemical Company | Modified alkyd compositions comprising diol latex compositions and processes of making the same |
| US7238840B2 (en) * | 2002-03-28 | 2007-07-03 | Huntsman International Llc | Process for the production of diaminodiphenylmethane and its higher homologues |
| BR0314423B1 (pt) | 2002-08-30 | 2013-04-30 | composiÇço de poliamida e processo para a preparaÇço de uma resina de epàxi curado (poli-eteralcanolamina) e de uma poliurÉia. | |
| US20070043197A1 (en) * | 2003-07-07 | 2007-02-22 | Huntsman Petrochemical Corporation | Polyurea polymers from secondary polyether polyamines |
| US8501828B2 (en) * | 2004-08-11 | 2013-08-06 | Huntsman Petrochemical Llc | Cure rebond binder |
| US20070066786A1 (en) * | 2005-09-22 | 2007-03-22 | The Hanson Group, Llc | Methods of preparing and using polyurea elastomers |
| US20070208157A1 (en) * | 2006-03-01 | 2007-09-06 | Huntsman Petrochemical Corporation | Polyurea polymers with improved flexibility using secondary polyetheramines |
| US20070208156A1 (en) * | 2006-03-01 | 2007-09-06 | Huntsman Petrochemical Corporation | Polyurea polymers with improved flexibility using secondary polyetheramines |
| AU2008224980B2 (en) | 2007-03-15 | 2012-11-08 | Huntsman Petrochemical Llc | High functionality amine compounds and uses therefor |
| US8290705B2 (en) * | 2007-04-25 | 2012-10-16 | Rio Sisa Idea Farm | Mobile navigation system with graphic crime-risk display |
| US8138378B2 (en) * | 2007-06-19 | 2012-03-20 | Huntsman Petrochemical Llc | Reactive amine catalysts for polyurethane foam |
| AU2008266219B2 (en) * | 2007-06-19 | 2013-05-23 | Huntsman Petrochemical Llc | Reactive amine catalysts for polyurethane foam |
| US20100272664A1 (en) * | 2007-11-28 | 2010-10-28 | Colgate-Palmolive Company | Alpha or Beta Hydroxy Acid Adducts of Oil |
| US8313809B2 (en) | 2007-12-11 | 2012-11-20 | Patrick Ilfrey | Same-day coatings and processes |
| WO2010053649A1 (en) | 2008-11-07 | 2010-05-14 | Huntsman Petrochemical Llc | Polyaminoacetonitriles, their methods of preparation and use |
| US20110132782A1 (en) | 2009-12-07 | 2011-06-09 | Patrick Ilfrey | Article and method for reactive mixtures |
| US9067865B2 (en) | 2009-12-22 | 2015-06-30 | Huntsman Petrochemical Llc | Etheramines and their use as intermediates for polymer synthesis |
| US9178156B2 (en) | 2009-12-23 | 2015-11-03 | Merck Patent Gmbh | Compositions comprising polymeric binders |
| US8865315B2 (en) | 2011-12-20 | 2014-10-21 | Huntsman International Llc | Self healing coating system for use with fuel tanks |
| AR098050A1 (es) | 2013-10-18 | 2016-04-27 | Huntsman Petrochemical Llc | Eteraminas con mayor estabilidad térmica y su uso como curativos o intermediarios para la síntesis de polímeros |
| JP6492070B2 (ja) | 2013-11-05 | 2019-03-27 | ハンツマン ペトロケミカル エルエルシーＨｕｎｔｓｍａｎ Ｐｅｔｒｏｃｈｅｍｉｃａｌ ＬＬＣ | エーテルアミンおよび、ポリマー合成のための硬化剤または中間体としてのそれらの使用 |
| CN107466304A (zh) | 2015-04-10 | 2017-12-12 | 巴斯夫欧洲公司 | 基于tdi液状残余物的绝热聚氨酯硬质泡沫 |
| KR102627551B1 (ko) | 2016-01-12 | 2024-01-23 | 헌츠만 페트로케미칼 엘엘씨 | 폴리에테르아민과 알킬렌 아민의 공-제조 |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2787601A (en) * | 1953-03-03 | 1957-04-02 | Du Pont | Cellular plastic materials which are condensation products of hydroxy containing fatty acid glycerides and arylene dhsocyanates |
-
0
- NL NL280259D patent/NL280259A/xx unknown
- DE DENDAT1071329D patent/DE1071329B/de active Pending
- BE BE567550D patent/BE567550A/xx unknown
-
1957
- 1957-05-10 GB GB14899/57A patent/GB848672A/en not_active Expired
-
1958
- 1958-05-02 US US732450A patent/US2950263A/en not_active Expired - Lifetime
- 1958-05-10 FR FR1200377D patent/FR1200377A/fr not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL280259A (OSRAM) | |
| BE567550A (OSRAM) | |
| US2950263A (en) | 1960-08-23 |
| GB848672A (en) | 1960-09-21 |
| FR1200377A (fr) | 1959-12-21 |
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