DE2529823C3 - Vernetzungsmittel für Polyurethanschaumstoffe - Google Patents
Vernetzungsmittel für PolyurethanschaumstoffeInfo
- Publication number
- DE2529823C3 DE2529823C3 DE2529823A DE2529823A DE2529823C3 DE 2529823 C3 DE2529823 C3 DE 2529823C3 DE 2529823 A DE2529823 A DE 2529823A DE 2529823 A DE2529823 A DE 2529823A DE 2529823 C3 DE2529823 C3 DE 2529823C3
- Authority
- DE
- Germany
- Prior art keywords
- methylenedianiline
- crosslinking agent
- polyurethane
- bis
- methylene
- 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
- 239000003431 cross linking reagent Substances 0.000 title claims description 23
- 239000011496 polyurethane foam Substances 0.000 title claims description 9
- 229920005830 Polyurethane Foam Polymers 0.000 title claims description 8
- YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 16
- 239000000047 product Substances 0.000 claims description 16
- 239000004814 polyurethane Substances 0.000 claims description 11
- 229920002635 polyurethane Polymers 0.000 claims description 11
- IBOFVQJTBBUKMU-UHFFFAOYSA-N 4,4'-methylene-bis-(2-chloroaniline) Chemical compound C1=C(Cl)C(N)=CC=C1CC1=CC=C(N)C(Cl)=C1 IBOFVQJTBBUKMU-UHFFFAOYSA-N 0.000 claims description 10
- 150000004985 diamines Chemical class 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 7
- 150000001875 compounds Chemical class 0.000 claims description 7
- 239000006260 foam Substances 0.000 claims description 7
- 230000015572 biosynthetic process Effects 0.000 claims description 5
- 230000001413 cellular effect Effects 0.000 claims description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 4
- -1 H. Ethylenediamine Chemical compound 0.000 claims description 4
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 229920005862 polyol Polymers 0.000 claims description 4
- 150000003077 polyols Chemical class 0.000 claims description 4
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 239000004615 ingredient Substances 0.000 claims description 3
- 230000009257 reactivity Effects 0.000 claims description 3
- 150000004984 aromatic diamines Chemical class 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 230000000711 cancerogenic effect Effects 0.000 claims description 2
- 238000004132 cross linking Methods 0.000 claims description 2
- 235000011187 glycerol Nutrition 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims 3
- 229920000233 poly(alkylene oxides) Polymers 0.000 claims 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims 2
- 230000000694 effects Effects 0.000 claims 2
- 229920000642 polymer Polymers 0.000 claims 2
- BFCFYVKQTRLZHA-UHFFFAOYSA-N 1-chloro-2-nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1Cl BFCFYVKQTRLZHA-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- XKXPBJBODVHDAW-UHFFFAOYSA-N 4-(4-amino-2-chlorophenyl)-3-chloroaniline Chemical compound ClC1=CC(N)=CC=C1C1=CC=C(N)C=C1Cl XKXPBJBODVHDAW-UHFFFAOYSA-N 0.000 claims 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 claims 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 claims 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 claims 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 claims 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims 1
- 229920005906 polyester polyol Polymers 0.000 claims 1
- 239000011148 porous material Substances 0.000 claims 1
- 239000000600 sorbitol Substances 0.000 claims 1
- 239000007858 starting material Substances 0.000 claims 1
- 239000000126 substance Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- 150000001412 amines Chemical class 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000000470 constituent Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
- HVCNXQOWACZAFN-UHFFFAOYSA-N 4-ethylmorpholine Chemical compound CCN1CCOCC1 HVCNXQOWACZAFN-UHFFFAOYSA-N 0.000 description 1
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 235000011089 carbon dioxide Nutrition 0.000 description 1
- 231100000357 carcinogen Toxicity 0.000 description 1
- 239000003183 carcinogenic agent Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- RTWNYYOXLSILQN-UHFFFAOYSA-N methanediamine Chemical compound NCN RTWNYYOXLSILQN-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000008961 swelling Effects 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
- 150000004998 toluenediamines Chemical class 0.000 description 1
- 238000011282 treatment Methods 0.000 description 1
- 239000000080 wetting agent Substances 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
- C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
- C08G18/6666—Compounds of group C08G18/48 or C08G18/52
- C08G18/667—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6681—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38
- C08G18/6688—Compounds of group C08G18/48 or C08G18/52 with compounds of group C08G18/32 or polyamines of C08G18/38 with compounds of group C08G18/32 or C08G18/3271 and/or polyamines of C08G18/38 with compounds of group C08G18/3271
-
- 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
- C08G18/32—Polyhydroxy compounds; Polyamines; Hydroxyamines
- C08G18/3271—Hydroxyamines
- C08G18/329—Hydroxyamines containing aromatic groups
-
- F—MECHANICAL ENGINEERING; LIGHTING; HEATING; WEAPONS; BLASTING
- F02—COMBUSTION ENGINES; HOT-GAS OR COMBUSTION-PRODUCT ENGINE PLANTS
- F02P—IGNITION, OTHER THAN COMPRESSION IGNITION, FOR INTERNAL-COMBUSTION ENGINES; TESTING OF IGNITION TIMING IN COMPRESSION-IGNITION ENGINES
- F02P9/00—Electric spark ignition control, not otherwise provided for
- F02P9/002—Control of spark intensity, intensifying, lengthening, suppression
- F02P9/007—Control of spark intensity, intensifying, lengthening, suppression by supplementary electrical discharge in the pre-ionised electrode interspace of the sparking plug, e.g. plasma jet ignition
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Physics & Mathematics (AREA)
- Plasma & Fusion (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- General Engineering & Computer Science (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/485,798 US3948825A (en) | 1974-07-05 | 1974-07-05 | Curing agent for use in making cellular polyurethane compositions |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2529823A1 DE2529823A1 (de) | 1976-01-15 |
| DE2529823B2 DE2529823B2 (de) | 1977-04-14 |
| DE2529823C3 true DE2529823C3 (de) | 1985-11-14 |
Family
ID=23929479
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2529823A Expired DE2529823C3 (de) | 1974-07-05 | 1975-07-04 | Vernetzungsmittel für Polyurethanschaumstoffe |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US3948825A (enExample) |
| AT (1) | AT343919B (enExample) |
| BE (1) | BE831052A (enExample) |
| CA (1) | CA1050048A (enExample) |
| CH (1) | CH601371A5 (enExample) |
| DE (1) | DE2529823C3 (enExample) |
| DK (1) | DK303175A (enExample) |
| ES (1) | ES439167A1 (enExample) |
| FR (1) | FR2277074A1 (enExample) |
| GB (1) | GB1478076A (enExample) |
| IT (1) | IT1036404B (enExample) |
| NL (1) | NL7508013A (enExample) |
| SE (1) | SE414930B (enExample) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4569952A (en) * | 1984-05-03 | 1986-02-11 | Mobay Chemical Corporation | Flexible polyurethane foams having improved load bearing characteristics and mixtures useful therein |
| US4743628A (en) * | 1986-08-06 | 1988-05-10 | Air Products And Chemicals, Inc. | Polyurethane foams incorporating alkoxylated aromatic diamine and acetylenic glycol |
| US4992484A (en) * | 1987-11-20 | 1991-02-12 | Air Products And Chemicals, Inc. | Polyurethane systems incorporating alkoxylated diethyltoluenediamine |
| US4876292A (en) * | 1988-10-06 | 1989-10-24 | Mobay Corporation | Isocyanate reactive mixture and the use thereof in the manufacture of flexible polyurethane foams |
| US5252624A (en) * | 1990-11-06 | 1993-10-12 | Miles Inc. | System for the production of toluene diisocyanate based flexible foams and the flexible foams produced therefrom |
| CA2052908A1 (en) * | 1990-11-06 | 1992-05-07 | Charles M. Milliren | System for the production of toluene diisocyanate based flexible foams and the flexible foams produced therefrom |
| US6376567B1 (en) * | 2000-12-07 | 2002-04-23 | Bayer Corporation | Polyisocyanate compositions and a process for the production of low-density flexible foams with low humid aged compression sets from these polyisocyanate compositions |
Family Cites Families (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| IT570070A (enExample) * | 1956-04-13 | |||
| IT699971A (enExample) * | 1958-08-15 | |||
| DE1112284B (de) * | 1959-01-16 | 1961-08-03 | Dunlop Rubber Co | Verfahren zur Herstellung von Schaumstoffen auf Polyurethangrundlage |
| BE619212A (enExample) * | 1961-06-22 | |||
| GB1049287A (en) * | 1962-07-16 | 1966-11-23 | Ici Ltd | New polyethers and polyurethanes |
| US3257339A (en) * | 1963-07-22 | 1966-06-21 | Union Carbide Corp | Reaction product of an organic polyiso-cyanate and an alkylene oxide adduct of a bis (aminophenyl) sulfone |
| US3314995A (en) * | 1963-12-09 | 1967-04-18 | Mobay Chemical Corp | Alkylene oxide adducts of bis(2, 4-diamino-5-methyl phenyl)methane |
| NL133349C (enExample) * | 1963-12-30 | |||
| US3438986A (en) * | 1965-05-21 | 1969-04-15 | Olin Mathieson | Oxyalkylated nitrogen compounds |
| GB1124799A (en) * | 1965-12-02 | 1968-08-21 | Ciba Ltd | Epoxide resin compositions |
| US3493525A (en) * | 1967-03-30 | 1970-02-03 | Mobay Chemical Corp | Polymethane foams prepared from alkylene oxide adducts of arylamines |
| DE2231529A1 (de) * | 1972-06-28 | 1974-01-10 | Bayer Ag | Verfahren zur herstellung von polyurethanschaumstoffen |
| IT1016145B (it) * | 1973-06-26 | 1977-05-30 | Dai Ichi Kogyo Seiyaku Co Ltd | Poliuretano espanso resistente alla fiamma e procedimento per preparar lo |
-
1974
- 1974-07-05 US US05/485,798 patent/US3948825A/en not_active Expired - Lifetime
-
1975
- 1975-05-15 CA CA227,065A patent/CA1050048A/en not_active Expired
- 1975-07-01 IT IT68687/75A patent/IT1036404B/it active
- 1975-07-02 AT AT508475A patent/AT343919B/de not_active IP Right Cessation
- 1975-07-03 GB GB2808775A patent/GB1478076A/en not_active Expired
- 1975-07-04 SE SE7507730A patent/SE414930B/xx not_active IP Right Cessation
- 1975-07-04 BE BE158032A patent/BE831052A/xx not_active IP Right Cessation
- 1975-07-04 DK DK303175A patent/DK303175A/da unknown
- 1975-07-04 NL NL7508013A patent/NL7508013A/xx not_active Application Discontinuation
- 1975-07-04 CH CH877775A patent/CH601371A5/xx not_active IP Right Cessation
- 1975-07-04 DE DE2529823A patent/DE2529823C3/de not_active Expired
- 1975-07-04 ES ES439167A patent/ES439167A1/es not_active Expired
- 1975-07-04 FR FR7521032A patent/FR2277074A1/fr active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| SE414930B (sv) | 1980-08-25 |
| AT343919B (de) | 1978-06-26 |
| SE7507730L (sv) | 1976-01-07 |
| GB1478076A (en) | 1977-06-29 |
| ES439167A1 (es) | 1977-06-16 |
| FR2277074B1 (enExample) | 1979-04-27 |
| DK303175A (da) | 1976-01-06 |
| DE2529823A1 (de) | 1976-01-15 |
| IT1036404B (it) | 1979-10-30 |
| DE2529823B2 (de) | 1977-04-14 |
| CH601371A5 (enExample) | 1978-07-14 |
| ATA508475A (de) | 1977-10-15 |
| US3948825A (en) | 1976-04-06 |
| BE831052A (fr) | 1976-01-05 |
| NL7508013A (nl) | 1976-01-07 |
| CA1050048A (en) | 1979-03-06 |
| FR2277074A1 (fr) | 1976-01-30 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8281 | Inventor (new situation) |
Free format text: PRAY, EDWARD RAWSON, DEARBORN, MICH., US |
|
| C3 | Grant after two publication steps (3rd publication) |