DE2239645C3 - Verfahren zur Herstellung von flüssigen, carbodiimidhaltigen organischen Polyisocyanaten - Google Patents
Verfahren zur Herstellung von flüssigen, carbodiimidhaltigen organischen PolyisocyanatenInfo
- Publication number
- DE2239645C3 DE2239645C3 DE2239645A DE2239645A DE2239645C3 DE 2239645 C3 DE2239645 C3 DE 2239645C3 DE 2239645 A DE2239645 A DE 2239645A DE 2239645 A DE2239645 A DE 2239645A DE 2239645 C3 DE2239645 C3 DE 2239645C3
- Authority
- DE
- Germany
- Prior art keywords
- carbodiimide
- chloromethyl
- tris
- organic
- liquid
- 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
- 239000005056 polyisocyanate Substances 0.000 title claims description 35
- 229920001228 polyisocyanate Polymers 0.000 title claims description 35
- 150000001718 carbodiimides Chemical class 0.000 title claims description 22
- 239000007788 liquid Substances 0.000 title claims description 19
- 238000000034 method Methods 0.000 title claims description 16
- 238000002360 preparation method Methods 0.000 title claims description 8
- 239000012948 isocyanate Substances 0.000 claims description 33
- 150000002513 isocyanates Chemical class 0.000 claims description 30
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 238000004519 manufacturing process Methods 0.000 claims description 15
- -1 carbodiimide isocyanate Chemical class 0.000 claims description 14
- 150000001875 compounds Chemical class 0.000 claims description 14
- 230000015572 biosynthetic process Effects 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 7
- GGECNORVQSLCLI-UHFFFAOYSA-N bis(chloromethyl)phosphoryl-chloromethane Chemical compound ClCP(=O)(CCl)CCl GGECNORVQSLCLI-UHFFFAOYSA-N 0.000 claims description 7
- 229910052698 phosphorus Inorganic materials 0.000 claims description 6
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims description 5
- 239000011574 phosphorus Substances 0.000 claims description 5
- 238000001816 cooling Methods 0.000 claims description 4
- 239000006260 foam Substances 0.000 claims description 4
- 238000010438 heat treatment Methods 0.000 claims description 3
- 239000004814 polyurethane Substances 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims 6
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims 3
- 238000005755 formation reaction Methods 0.000 claims 3
- AUONHKJOIZSQGR-UHFFFAOYSA-N oxophosphane Chemical compound P=O AUONHKJOIZSQGR-UHFFFAOYSA-N 0.000 claims 3
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 claims 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 claims 2
- 239000007983 Tris buffer Substances 0.000 claims 2
- RAABOESOVLLHRU-UHFFFAOYSA-N diazene Chemical compound N=N RAABOESOVLLHRU-UHFFFAOYSA-N 0.000 claims 2
- 229910000071 diazene Inorganic materials 0.000 claims 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 claims 2
- 230000009257 reactivity Effects 0.000 claims 2
- RPAJSBKBKSSMLJ-DFWYDOINSA-N (2s)-2-aminopentanedioic acid;hydrochloride Chemical class Cl.OC(=O)[C@@H](N)CCC(O)=O RPAJSBKBKSSMLJ-DFWYDOINSA-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
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- AVCYPPTVQFMAGG-UHFFFAOYSA-N ClC[PH2]=O Chemical compound ClC[PH2]=O AVCYPPTVQFMAGG-UHFFFAOYSA-N 0.000 claims 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims 1
- 229910002092 carbon dioxide Inorganic materials 0.000 claims 1
- 239000001569 carbon dioxide Substances 0.000 claims 1
- 230000003197 catalytic effect Effects 0.000 claims 1
- 238000006555 catalytic reaction Methods 0.000 claims 1
- USJRLGNYCQWLPF-UHFFFAOYSA-N chlorophosphane Chemical compound ClP USJRLGNYCQWLPF-UHFFFAOYSA-N 0.000 claims 1
- 239000003063 flame retardant Substances 0.000 claims 1
- 125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 claims 1
- AIRPJJGSWHWBKS-UHFFFAOYSA-N hydroxymethylphosphanium;chloride Chemical compound [Cl-].OC[PH3+] AIRPJJGSWHWBKS-UHFFFAOYSA-N 0.000 claims 1
- 150000003949 imides Chemical class 0.000 claims 1
- 150000002989 phenols Chemical class 0.000 claims 1
- 125000004437 phosphorous atom Chemical group 0.000 claims 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 claims 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 claims 1
- 239000011734 sodium Substances 0.000 claims 1
- 229910052708 sodium Inorganic materials 0.000 claims 1
- 238000005829 trimerization reaction Methods 0.000 claims 1
- LENZDBCJOHFCAS-UHFFFAOYSA-N tris Chemical compound OCC(N)(CO)CO LENZDBCJOHFCAS-UHFFFAOYSA-N 0.000 claims 1
- WKIBACLZWXDUMC-UHFFFAOYSA-N tris(chloromethyl)phosphane Chemical compound ClCP(CCl)CCl WKIBACLZWXDUMC-UHFFFAOYSA-N 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 18
- 239000000047 product Substances 0.000 description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 10
- 229920005862 polyol Polymers 0.000 description 9
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 8
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 description 7
- 229920000728 polyester Polymers 0.000 description 7
- 150000007513 acids Chemical class 0.000 description 6
- 125000002947 alkylene group Chemical group 0.000 description 6
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 6
- 150000003077 polyols Chemical class 0.000 description 6
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
- 229920001281 polyalkylene Polymers 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 238000004448 titration Methods 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 239000012467 final product Substances 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 238000004458 analytical method Methods 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- 150000005846 sugar alcohols Polymers 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 2
- 150000001913 cyanates Chemical class 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 150000004985 diamines Chemical class 0.000 description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 description 2
- 238000002329 infrared spectrum Methods 0.000 description 2
- 229920006324 polyoxymethylene Polymers 0.000 description 2
- 229920006295 polythiol Polymers 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- JIABEENURMZTTI-UHFFFAOYSA-N 1-isocyanato-2-[(2-isocyanatophenyl)methyl]benzene Chemical compound O=C=NC1=CC=CC=C1CC1=CC=CC=C1N=C=O JIABEENURMZTTI-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- 229930182556 Polyacetal Natural products 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- VGNXHRVCGURILB-UHFFFAOYSA-N isocyanic acid;phenol Chemical compound N=C=O.OC1=CC=CC=C1 VGNXHRVCGURILB-UHFFFAOYSA-N 0.000 description 1
- 239000012263 liquid product Substances 0.000 description 1
- 230000014759 maintenance of location Effects 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- 150000003016 phosphoric acids Chemical class 0.000 description 1
- 229920001748 polybutylene Polymers 0.000 description 1
- 229920006149 polyester-amide block copolymer Polymers 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
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 150000003573 thiols Chemical class 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
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 230000004580 weight loss Effects 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
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C267/00—Carbodiimides
-
- 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
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S521/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S521/901—Cellular polymer containing a carbodiimide structure
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 |
|---|---|---|---|
| US17172571A | 1971-08-13 | 1971-08-13 |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2239645A1 DE2239645A1 (de) | 1973-03-01 |
| DE2239645B2 DE2239645B2 (de) | 1975-01-16 |
| DE2239645C3 true DE2239645C3 (de) | 1975-09-04 |
Family
ID=22624888
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2239645A Expired DE2239645C3 (de) | 1971-08-13 | 1972-08-11 | Verfahren zur Herstellung von flüssigen, carbodiimidhaltigen organischen Polyisocyanaten |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US3761502A (OSRAM) |
| JP (1) | JPS5037172B2 (OSRAM) |
| BE (1) | BE787395A (OSRAM) |
| CA (1) | CA999301A (OSRAM) |
| DE (1) | DE2239645C3 (OSRAM) |
| FR (1) | FR2150099A5 (OSRAM) |
| GB (1) | GB1359619A (OSRAM) |
| IT (1) | IT961977B (OSRAM) |
| NL (1) | NL149516B (OSRAM) |
| ZA (1) | ZA725280B (OSRAM) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1397469A (en) * | 1973-01-15 | 1975-06-11 | Ici Ltd | Process for converting isocyanate groups to carbodiimide groups |
| DE2504400A1 (de) * | 1975-02-01 | 1976-08-05 | Bayer Ag | Lagerstabile, carbodiimidgruppen enthaltende polyisocyanate |
| DE2504334A1 (de) * | 1975-02-01 | 1976-08-05 | Bayer Ag | Hochmolekulare, unloesliche carbodiimidisierungskatalysatoren |
| GB1483957A (en) * | 1975-05-19 | 1977-08-24 | Ici Ltd | Diphenylmethane diisocyanate compositions |
| GB1567713A (en) * | 1977-01-31 | 1980-05-21 | Upjohn Co | Process for preparing carbodiimide-containing polyisocyanates |
| US4154752A (en) * | 1978-05-05 | 1979-05-15 | Mobay Chemical Corporation | Preparation of partially carbodiimidized methylenebis (phenyl isocyanate) |
| US4198489A (en) * | 1978-10-30 | 1980-04-15 | Basf Wyandotte Corporation | Polyurethane foams prepared from highly stable liquid carbodiimide-containing 4,4'-diphenylmethane diisocyanate |
| US4199524A (en) * | 1978-10-30 | 1980-04-22 | Basf Wyandotte Corporation | Stable liquid carbodiimide-containing polyisocyanate compositions |
| US4177205A (en) * | 1978-11-20 | 1979-12-04 | Basf Wyandotte Corporation | Process for the preparation of highly stable liquid carbodiimide-containing polyisocyanate compositions |
| US4294951A (en) * | 1980-07-14 | 1981-10-13 | Mitsui-Nisso Corporation | Rapid curing polyurethane elastomer prepared from a diphenylmethanediisocyanate based liquid prepolymer and a curing agent containing a polytetramethylene ether glycol, a diol and an organometallic catalyst |
| US4306052A (en) * | 1980-09-25 | 1981-12-15 | The Upjohn Company | Thermoplastic polyester polyurethanes |
| DE3609687A1 (de) * | 1985-03-29 | 1986-10-02 | Nisshinbo Industries, Inc., Tokio/Tokyo | Duroplastisches harz und verfahren zu seiner erzeugung |
| DE102009027246A1 (de) * | 2009-06-26 | 2010-12-30 | Evonik Degussa Gmbh | Katalysatorarme Carbodiimidgruppen und/oder Uretonimingruppen aufweisende Isocyanatmischungen |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3152162A (en) * | 1959-07-29 | 1964-10-06 | Bayer Ag | Polyisocyanate-carbodiimide adducts and process for the production thereof |
| DE1156401B (de) * | 1960-05-24 | 1963-10-31 | Bayer Ag | Verfahren zur Herstellung von Carbodiimiden |
| US3522303A (en) * | 1964-08-12 | 1970-07-28 | Upjohn Co | Phosphorous compounds |
| US3635947A (en) * | 1967-01-10 | 1972-01-18 | Olin Mathieson | Catalytic process for the preparation of monocarbodiimides and isocyanate-monocarbodiimide adducts |
-
0
- BE BE787395D patent/BE787395A/xx unknown
-
1971
- 1971-08-13 US US00171725A patent/US3761502A/en not_active Expired - Lifetime
-
1972
- 1972-08-01 GB GB3593072A patent/GB1359619A/en not_active Expired
- 1972-08-01 ZA ZA725280A patent/ZA725280B/xx unknown
- 1972-08-01 CA CA148,413A patent/CA999301A/en not_active Expired
- 1972-08-08 NL NL727210861A patent/NL149516B/xx not_active IP Right Cessation
- 1972-08-11 IT IT52132/72A patent/IT961977B/it active
- 1972-08-11 FR FR7229146A patent/FR2150099A5/fr not_active Expired
- 1972-08-11 DE DE2239645A patent/DE2239645C3/de not_active Expired
- 1972-08-14 JP JP47080819A patent/JPS5037172B2/ja not_active Expired
Also Published As
| Publication number | Publication date |
|---|---|
| NL7210861A (OSRAM) | 1973-02-15 |
| BE787395A (fr) | 1973-02-12 |
| AU4534172A (en) | 1973-09-06 |
| CA999301A (en) | 1976-11-02 |
| DE2239645B2 (de) | 1975-01-16 |
| IT961977B (it) | 1973-12-10 |
| JPS5037172B2 (OSRAM) | 1975-12-01 |
| US3761502A (en) | 1973-09-25 |
| NL149516B (nl) | 1976-05-17 |
| DE2239645A1 (de) | 1973-03-01 |
| ZA725280B (en) | 1973-04-25 |
| GB1359619A (en) | 1974-07-10 |
| JPS4828450A (OSRAM) | 1973-04-14 |
| FR2150099A5 (OSRAM) | 1973-03-30 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2502330C2 (de) | Verfahren zur Herstellung eines zelligen Polymeren, dessen hauptsächlich wiederkehrende Einheit aus einer Isocyanurateinheit besteht | |
| DE2239645C3 (de) | Verfahren zur Herstellung von flüssigen, carbodiimidhaltigen organischen Polyisocyanaten | |
| DE2456469C2 (de) | Verfahren zur Herstellung von in Wasser löslichen bzw. dispergierbaren blockierten Polyisocyanaten und ihre Verwendung als Beschichtungsmittel | |
| DE3103757C2 (OSRAM) | ||
| DE3629560A1 (de) | Polyepichlorhydrin mit endstaendigen hydroxylgruppen und seine derivate | |
| DE1170628B (de) | Verfahren zur Herstellung von, gegebenenfalls verschaeumten, Polyurethanen | |
| DE2527242A1 (de) | Cokatalysatorsystem zur trimerisierung eines polyisocyanats und verfahren zur herstellung eines zelligen polymeren mit vornehmlich wiederkehrenden isocyanurateinheiten | |
| DE1923936A1 (de) | Esterhaltige Polyole,ihre Herstellung und Verwendung | |
| DE2733087A1 (de) | Verfahren zur herstellung von urethan-modifizierten polyisocyanurat- hartschaeumen | |
| DE2658391A1 (de) | Verfahren zur herstellung von urethan-modifizierten polyisocyanurat- hartschaeumen | |
| DE2726779A1 (de) | Verfahren zur umsetzung von isocyanaten | |
| DE3883854T2 (de) | Verfahren zur Herstellung von Hartschäumen. | |
| DE69129434T2 (de) | Kontinuierliches Verfahren zur Herstellung von Isocyanat enthaltenden Präpolymeren und daraus hergestellte Polyurethan-Schäume | |
| DE2539982A1 (de) | Polyurethane und verfahren zu ihrer herstellung | |
| DE2752419A1 (de) | Urethanmodifizierte isocyanurat- schaumstoffe mit verbesserten physikalischen eigenschaften | |
| EP0001800A1 (de) | Polyätherpolyole, Verfahren zu ihrer Herstellung und Verfahren zur Herstellung von Polyurethanschaumstoffen | |
| DE2513741C3 (de) | Verfahren zur Herstellung eines flammfesten rauchbeständigen Polyurethan-Weichschaumstoffs | |
| DE2102604B2 (de) | Verfahren zur Herstellung von Polymerschaumstoffen mit Carb-odiimid-Isocyanurat- und NCO-Gruppen | |
| DE1191098B (de) | Verfahren zur Herstellung von Polyurethanschaumstoffen | |
| DE2649226A1 (de) | Polyole, verfahren zu ihrer herstellung und ihre verwendung bei der herstellung feuerhemmender schaumstoffe | |
| DE2543114A1 (de) | Herstellung von isocyanuratschaeumen | |
| DE2257273A1 (de) | Starrer schaumstoff und verfahren zu dessen herstellung | |
| DE1243865B (de) | Polyisocyanatmischungen zur Herstellung von Kunststoffen | |
| DE2648594A1 (de) | Verfahren zur herstellung eines kunststoff-schaums und eine zur katalysierung dieses verfahrens geeignete verbindung | |
| DE1720953B2 (de) | Verfahren zur Herstellung von harten, Isocyanuratringstrukturen enthaltenden Schaumstoffen |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| C3 | Grant after two publication steps (3rd publication) | ||
| E77 | Valid patent as to the heymanns-index 1977 | ||
| 8339 | Ceased/non-payment of the annual fee |