DE2524476A1 - Aromatische uretdion-diisocyanat- disulfonsaeuren ein verfahren zu ihrer herstellung, sowie ihre verwendung - Google Patents
Aromatische uretdion-diisocyanat- disulfonsaeuren ein verfahren zu ihrer herstellung, sowie ihre verwendungInfo
- Publication number
- DE2524476A1 DE2524476A1 DE19752524476 DE2524476A DE2524476A1 DE 2524476 A1 DE2524476 A1 DE 2524476A1 DE 19752524476 DE19752524476 DE 19752524476 DE 2524476 A DE2524476 A DE 2524476A DE 2524476 A1 DE2524476 A1 DE 2524476A1
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- uretdione
- aromatic
- isocyanate
- uretdione diisocyanate
- 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.)
- Withdrawn
Links
- 238000000034 method Methods 0.000 title claims description 18
- 239000002253 acid Substances 0.000 title claims description 12
- 150000007513 acids Chemical class 0.000 title claims description 10
- 238000004519 manufacturing process Methods 0.000 title claims description 8
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 title description 19
- 125000005442 diisocyanate group Chemical group 0.000 claims description 22
- 238000006243 chemical reaction Methods 0.000 claims description 10
- 239000004814 polyurethane Substances 0.000 claims description 9
- 229920002635 polyurethane Polymers 0.000 claims description 8
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 claims description 8
- 150000001875 compounds Chemical class 0.000 claims description 6
- 239000012948 isocyanate Substances 0.000 claims description 6
- 150000002513 isocyanates Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 239000012442 inert solvent Substances 0.000 claims description 3
- 229920003023 plastic Polymers 0.000 claims description 3
- 239000004033 plastic Substances 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003545 alkoxy group Chemical group 0.000 claims description 2
- 229910052799 carbon Inorganic materials 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 239000011261 inert gas Substances 0.000 claims 1
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 12
- 125000003118 aryl group Chemical group 0.000 description 9
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 8
- 238000006277 sulfonation reaction Methods 0.000 description 8
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 7
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 5
- 239000007788 liquid Substances 0.000 description 5
- 239000000843 powder Substances 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 125000000542 sulfonic acid group Chemical group 0.000 description 4
- 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 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- 238000006471 dimerization reaction Methods 0.000 description 3
- 238000002329 infrared spectrum Methods 0.000 description 3
- 230000010354 integration Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- KDLIYVDINLSKGR-UHFFFAOYSA-N 1-isocyanato-4-(4-isocyanatophenoxy)benzene Chemical compound C1=CC(N=C=O)=CC=C1OC1=CC=C(N=C=O)C=C1 KDLIYVDINLSKGR-UHFFFAOYSA-N 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 238000005481 NMR spectroscopy Methods 0.000 description 2
- XYFCBTPGUUZFHI-UHFFFAOYSA-N Phosphine Chemical compound P XYFCBTPGUUZFHI-UHFFFAOYSA-N 0.000 description 2
- 229920002396 Polyurea Polymers 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- 231100000252 nontoxic Toxicity 0.000 description 2
- 230000003000 nontoxic effect Effects 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HVBSAKJJOYLTQU-UHFFFAOYSA-N 4-aminobenzenesulfonic acid Chemical class NC1=CC=C(S(O)(=O)=O)C=C1 HVBSAKJJOYLTQU-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- 241000551547 Dione <red algae> Species 0.000 description 1
- -1 Nitromathan Chemical compound 0.000 description 1
- 229920001944 Plastisol Polymers 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 230000002378 acidificating effect Effects 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical group 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- IJDKVJZZQBHKHI-UHFFFAOYSA-N bis(4-isocyanatophenyl)methanone Chemical compound C1=CC(N=C=O)=CC=C1C(=O)C1=CC=C(N=C=O)C=C1 IJDKVJZZQBHKHI-UHFFFAOYSA-N 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000010276 construction Methods 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229920000554 ionomer Polymers 0.000 description 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
- 229910000073 phosphorus hydride Inorganic materials 0.000 description 1
- 239000004999 plastisol Substances 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920003226 polyurethane urea Polymers 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 230000001105 regulatory effect Effects 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000012258 stirred mixture Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- IIACRCGMVDHOTQ-UHFFFAOYSA-N sulfamic acid Chemical class NS(O)(=O)=O IIACRCGMVDHOTQ-UHFFFAOYSA-N 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 238000003786 synthesis reaction Methods 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
- 239000003440 toxic substance Substances 0.000 description 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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
- C08G18/77—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
- C08G18/798—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing urethdione groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D229/00—Heterocyclic compounds containing rings of less than five members having two nitrogen atoms as the only ring hetero atoms
-
- 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
- C08G18/0804—Manufacture of polymers containing ionic or ionogenic groups
- C08G18/0819—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups
- C08G18/0828—Manufacture of polymers containing ionic or ionogenic groups containing anionic or anionogenic groups containing sulfonate groups or groups forming them
-
- 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
- C08G18/775—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur sulfur
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polyurethanes Or Polyureas (AREA)
Priority Applications (12)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752524476 DE2524476A1 (de) | 1975-06-03 | 1975-06-03 | Aromatische uretdion-diisocyanat- disulfonsaeuren ein verfahren zu ihrer herstellung, sowie ihre verwendung |
| ES448292A ES448292A1 (es) | 1975-06-03 | 1976-05-28 | Procedimiento para la obtencion de acidos uretdion-diisocia-natos-disulfonicos. |
| CH678776A CH628334A5 (en) | 1975-06-03 | 1976-05-31 | Process for the preparation of aromatic uretdione diisocyanate disulphonic acids, and the use thereof |
| AT401276A AT349031B (de) | 1975-06-03 | 1976-06-01 | Verfahren zur herstellung von neuen aromatischen uretdion-diisocyanat- disulfonsaeuren |
| IT49756/76A IT1061348B (it) | 1975-06-03 | 1976-06-01 | Acidi uretodion diisocianato disolfonici aromatici e procedimento per la loro produzione ed applicazione |
| JP51063679A JPS51146456A (en) | 1975-06-03 | 1976-06-02 | Preparation and use of aromatic uretodionee diisocyanateedisulphonic acid |
| BE167557A BE842493A (fr) | 1975-06-03 | 1976-06-02 | Acides uret-dione-diisocyanate-disulfoniques aromatiques, leur preparation et leurs utilisations |
| GB22753/76A GB1494467A (en) | 1975-06-03 | 1976-06-02 | Aromatic uretdione-diisocyanate-disulphonic acids a process for the preparation thereof and the use thereof |
| SE7606220A SE7606220L (sv) | 1975-06-03 | 1976-06-02 | Aromatiska uretdion-diisocyanat-disulfonsyror till anvendning vid framstellning av polyuretanplaster och sett att framstella dessa disulfonsyror |
| NL7606020A NL7606020A (nl) | 1975-06-03 | 1976-06-03 | Aromatische ureetdion-diisocyanaat-disulfon- zuren, werkwijze voor het bereiden ervan als- mede werkwijze voor het bereiden van polyurethan- -kunststoffen. |
| FR7616880A FR2313368A1 (fr) | 1975-06-03 | 1976-06-03 | Acides uret-dione-diisocyanate-disulfoniques aromatiques, leur preparation et leurs utilisations |
| US05/848,969 US4176118A (en) | 1975-06-03 | 1977-11-07 | Aromatic uretdione-diisocyanate-disulphonic acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19752524476 DE2524476A1 (de) | 1975-06-03 | 1975-06-03 | Aromatische uretdion-diisocyanat- disulfonsaeuren ein verfahren zu ihrer herstellung, sowie ihre verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2524476A1 true DE2524476A1 (de) | 1976-12-23 |
Family
ID=5948072
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19752524476 Withdrawn DE2524476A1 (de) | 1975-06-03 | 1975-06-03 | Aromatische uretdion-diisocyanat- disulfonsaeuren ein verfahren zu ihrer herstellung, sowie ihre verwendung |
Country Status (11)
| Country | Link |
|---|---|
| JP (1) | JPS51146456A (enExample) |
| AT (1) | AT349031B (enExample) |
| BE (1) | BE842493A (enExample) |
| CH (1) | CH628334A5 (enExample) |
| DE (1) | DE2524476A1 (enExample) |
| ES (1) | ES448292A1 (enExample) |
| FR (1) | FR2313368A1 (enExample) |
| GB (1) | GB1494467A (enExample) |
| IT (1) | IT1061348B (enExample) |
| NL (1) | NL7606020A (enExample) |
| SE (1) | SE7606220L (enExample) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074023A1 (de) * | 1981-09-08 | 1983-03-16 | Bayer Ag | Uretdiongruppen aufweisendes Diisocyanat, ein Verfahren zur Herstellung von hitzevernetzbaren Oligoadditionsprodukten und deren Verwendung zur Herstellung von hochmolekularen Kunststoffen |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2851341A1 (de) | 1978-11-28 | 1980-06-04 | Bayer Ag | Dispersionen aromatischer isocyanatosulfonsaeure-uretdione in organischen polyisocyanaten und ein verfahren zu ihrer herstellung |
| DE3232736A1 (de) * | 1982-09-03 | 1984-03-08 | Bayer Ag, 5090 Leverkusen | Aromatische uretdion-di-harnstoff-diamine, verfahren zu ihrer herstellung und ihre verwendung bei der polyurethansynthese |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR1530991A (fr) * | 1966-07-18 | 1968-06-28 | Uniroyal | Procédé de dimérisation de di-isocyanates aromatiques en dispersion aqueuse |
| FR2249873A1 (en) * | 1973-10-31 | 1975-05-30 | Bakhitov Mansur | 2,4-Toluylene diisocyanate dimer prepn. - catalysed by trialkyl phosphite under heat removal conditions opt in inert solvent |
| DE2452390C2 (de) * | 1974-11-05 | 1983-12-29 | Bayer Ag, 5090 Leverkusen | Verfahren zur kontinuierlichen Herstellung von aromatischen Uretdiongruppen aufweisenden Polyisocyanaten |
-
1975
- 1975-06-03 DE DE19752524476 patent/DE2524476A1/de not_active Withdrawn
-
1976
- 1976-05-28 ES ES448292A patent/ES448292A1/es not_active Expired
- 1976-05-31 CH CH678776A patent/CH628334A5/de not_active IP Right Cessation
- 1976-06-01 AT AT401276A patent/AT349031B/de not_active IP Right Cessation
- 1976-06-01 IT IT49756/76A patent/IT1061348B/it active
- 1976-06-02 BE BE167557A patent/BE842493A/xx unknown
- 1976-06-02 JP JP51063679A patent/JPS51146456A/ja active Pending
- 1976-06-02 GB GB22753/76A patent/GB1494467A/en not_active Expired
- 1976-06-02 SE SE7606220A patent/SE7606220L/xx unknown
- 1976-06-03 NL NL7606020A patent/NL7606020A/xx not_active Application Discontinuation
- 1976-06-03 FR FR7616880A patent/FR2313368A1/fr active Granted
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0074023A1 (de) * | 1981-09-08 | 1983-03-16 | Bayer Ag | Uretdiongruppen aufweisendes Diisocyanat, ein Verfahren zur Herstellung von hitzevernetzbaren Oligoadditionsprodukten und deren Verwendung zur Herstellung von hochmolekularen Kunststoffen |
Also Published As
| Publication number | Publication date |
|---|---|
| ATA401276A (de) | 1978-08-15 |
| ES448292A1 (es) | 1977-07-16 |
| FR2313368B1 (enExample) | 1982-01-08 |
| IT1061348B (it) | 1983-02-28 |
| SE7606220L (sv) | 1976-12-04 |
| AT349031B (de) | 1979-03-12 |
| FR2313368A1 (fr) | 1976-12-31 |
| GB1494467A (en) | 1977-12-07 |
| NL7606020A (nl) | 1976-12-07 |
| BE842493A (fr) | 1976-12-02 |
| JPS51146456A (en) | 1976-12-16 |
| CH628334A5 (en) | 1982-02-26 |
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