DE2025900C3 - Verfahren zur Herstellung von Polyurethanelastomeren - Google Patents
Verfahren zur Herstellung von PolyurethanelastomerenInfo
- Publication number
- DE2025900C3 DE2025900C3 DE2025900A DE2025900A DE2025900C3 DE 2025900 C3 DE2025900 C3 DE 2025900C3 DE 2025900 A DE2025900 A DE 2025900A DE 2025900 A DE2025900 A DE 2025900A DE 2025900 C3 DE2025900 C3 DE 2025900C3
- Authority
- DE
- Germany
- Prior art keywords
- diisocyanate
- din
- polyurethane elastomers
- diisocyanates
- diamines
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 229920003225 polyurethane elastomer Polymers 0.000 title claims description 9
- 238000004519 manufacturing process Methods 0.000 title claims description 6
- 239000004970 Chain extender Substances 0.000 claims description 14
- 125000005442 diisocyanate group Chemical group 0.000 claims description 13
- 150000001875 compounds Chemical class 0.000 claims description 8
- 150000004985 diamines Chemical class 0.000 claims description 7
- 150000004984 aromatic diamines Chemical class 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 15
- 239000000203 mixture Substances 0.000 description 15
- 229920002635 polyurethane Polymers 0.000 description 11
- 239000004814 polyurethane Substances 0.000 description 11
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 7
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 6
- 235000019589 hardness Nutrition 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 5
- 239000000155 melt Substances 0.000 description 5
- 229920003023 plastic Polymers 0.000 description 5
- 239000004033 plastic Substances 0.000 description 5
- 229920000728 polyester Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 4
- 125000004432 carbon atom Chemical group C* 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
- QCESOQYTNNRNNY-UHFFFAOYSA-N 4-bromo-3,5-difluorobenzenesulfonyl chloride Chemical compound FC1=CC(S(Cl)(=O)=O)=CC(F)=C1Br QCESOQYTNNRNNY-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- -1 aromatic compounds Diamines Chemical class 0.000 description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005842 heteroatom Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- FWJFNQHPFXHOAC-UHFFFAOYSA-N methyl 2,4-diaminobenzoate Chemical compound COC(=O)C1=CC=C(N)C=C1N FWJFNQHPFXHOAC-UHFFFAOYSA-N 0.000 description 3
- IYWLDOMAEQHKJZ-UHFFFAOYSA-N methyl 3,5-diaminobenzoate Chemical compound COC(=O)C1=CC(N)=CC(N)=C1 IYWLDOMAEQHKJZ-UHFFFAOYSA-N 0.000 description 3
- 229910052760 oxygen Inorganic materials 0.000 description 3
- 239000001301 oxygen Substances 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- 229910052717 sulfur Inorganic materials 0.000 description 3
- 239000011593 sulfur Substances 0.000 description 3
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- YXQZUZIULOEMPI-UHFFFAOYSA-N 2-methylpropyl 3,5-diaminobenzoate Chemical compound CC(C)COC(=O)C1=CC(N)=CC(N)=C1 YXQZUZIULOEMPI-UHFFFAOYSA-N 0.000 description 2
- VYWYYJYRVSBHJQ-UHFFFAOYSA-N 3,5-dinitrobenzoic acid Chemical class OC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 VYWYYJYRVSBHJQ-UHFFFAOYSA-N 0.000 description 2
- ZIIGSRYPZWDGBT-UHFFFAOYSA-N 610-30-0 Chemical compound OC(=O)C1=CC=C([N+]([O-])=O)C=C1[N+]([O-])=O ZIIGSRYPZWDGBT-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 2
- 239000007868 Raney catalyst Substances 0.000 description 2
- 229910000564 Raney nickel Inorganic materials 0.000 description 2
- NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001414 amino alcohols Chemical class 0.000 description 2
- 239000003054 catalyst Substances 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 238000001816 cooling Methods 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 150000002009 diols Chemical class 0.000 description 2
- FZWBABZIGXEXES-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O FZWBABZIGXEXES-UHFFFAOYSA-N 0.000 description 2
- UVSDPQBAKJACCV-UHFFFAOYSA-N ethene;hexanedioic acid Chemical group C=C.OC(=O)CCCCC(O)=O UVSDPQBAKJACCV-UHFFFAOYSA-N 0.000 description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910000041 hydrogen chloride Inorganic materials 0.000 description 2
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
- 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 2
- ZTNJGMFHJYGMDR-UHFFFAOYSA-N 1,2-diisocyanatoethane Chemical compound O=C=NCCN=C=O ZTNJGMFHJYGMDR-UHFFFAOYSA-N 0.000 description 1
- PQDIQKXGPYOGDI-UHFFFAOYSA-N 1,3,5-triisocyanatobenzene Chemical compound O=C=NC1=CC(N=C=O)=CC(N=C=O)=C1 PQDIQKXGPYOGDI-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- OVBFMUAFNIIQAL-UHFFFAOYSA-N 1,4-diisocyanatobutane Chemical compound O=C=NCCCCN=C=O OVBFMUAFNIIQAL-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- SINBGNJPYWNUQI-UHFFFAOYSA-N 2,2,2-trifluoro-1-imidazol-1-ylethanone Chemical compound FC(F)(F)C(=O)N1C=CN=C1 SINBGNJPYWNUQI-UHFFFAOYSA-N 0.000 description 1
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- FJVMXRNBCDETRE-UHFFFAOYSA-N CC1CCCCC1.CC(C)(C1)CC(C)(CN=C=O)CC1N=C=O.N=C=O.N=C=O Chemical compound CC1CCCCC1.CC(C)(C1)CC(C)(CN=C=O)CC1N=C=O.N=C=O.N=C=O FJVMXRNBCDETRE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 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 description 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 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 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
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 230000006735 deficit Effects 0.000 description 1
- 229920001971 elastomer Polymers 0.000 description 1
- 239000000806 elastomer Substances 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 150000002440 hydroxy compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- POGCCFLNFPIIGW-UHFFFAOYSA-N methyl 3,5-dinitrobenzoate Chemical compound COC(=O)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1 POGCCFLNFPIIGW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- APDDGKXWCXEDKS-UHFFFAOYSA-N octadecyl 3,5-diaminobenzoate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)C1=CC(N)=CC(N)=C1 APDDGKXWCXEDKS-UHFFFAOYSA-N 0.000 description 1
- GSYWWZYVHLJHCW-UHFFFAOYSA-N octyl 3,5-diaminobenzoate Chemical compound CCCCCCCCOC(=O)C1=CC(N)=CC(N)=C1 GSYWWZYVHLJHCW-UHFFFAOYSA-N 0.000 description 1
- 229920001521 polyalkylene glycol ether Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920006295 polythiol Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000003672 processing method Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 230000000630 rising effect Effects 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 229960004793 sucrose Drugs 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 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
- 125000005628 tolylene group Chemical group 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 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
- C08G18/28—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
- C08G18/6505—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen the low-molecular compounds being compounds of group C08G18/32 or polyamines of C08G18/38
- C08G18/6523—Compounds of group C08G18/3225 or C08G18/3271 or polyamines of C08G18/38
- C08G18/6529—Compounds of group C08G18/3225 or polyamines of C08G18/38
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C205/00—Compounds containing nitro groups bound to a carbon skeleton
- C07C205/49—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups
- C07C205/57—Compounds containing nitro groups bound to a carbon skeleton the carbon skeleton being further substituted by carboxyl groups having nitro groups and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
-
- 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
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
- C08G18/3821—Carboxylic acids; Esters thereof with monohydroxyl compounds
-
- 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
- Y10S528/00—Synthetic resins or natural rubbers -- part of the class 520 series
- Y10S528/906—Fiber or elastomer prepared from an isocyanate reactant
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)
Priority Applications (11)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2025900A DE2025900C3 (de) | 1970-05-27 | 1970-05-27 | Verfahren zur Herstellung von Polyurethanelastomeren |
| CH643671A CH549070A (de) | 1970-05-27 | 1971-04-30 | Verfahren zur herstellung neuer polyurethanelastomere. |
| US00145480A US3794621A (en) | 1970-05-27 | 1971-05-20 | Polyurethane elastomers prepared from diamino-benzoic acid esters |
| GB1619171*[A GB1354523A (en) | 1970-05-27 | 1971-05-21 | Polyurethane elastomers and a process for their preparation |
| CA113,719A CA965195A (en) | 1970-05-27 | 1971-05-21 | Polyurethane elastomers and a process for their preparation |
| SE7106807A SE378111B (https=) | 1970-05-27 | 1971-05-26 | |
| JP46035592A JPS5110279B1 (https=) | 1970-05-27 | 1971-05-26 | |
| NL7107259A NL7107259A (https=) | 1970-05-27 | 1971-05-26 | |
| AT459871A AT316870B (de) | 1970-05-27 | 1971-05-27 | Verfahren zur Herstellung von neuen Polyurethan-Elastomeren |
| BE767746A BE767746A (fr) | 1970-05-27 | 1971-05-27 | Nouveaux elastomeres de polyurethanes et leur procede de preparation |
| FR7119343A FR2090331B1 (https=) | 1970-05-27 | 1971-05-27 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2025900A DE2025900C3 (de) | 1970-05-27 | 1970-05-27 | Verfahren zur Herstellung von Polyurethanelastomeren |
Publications (3)
| Publication Number | Publication Date |
|---|---|
| DE2025900A1 DE2025900A1 (de) | 1971-12-02 |
| DE2025900B2 DE2025900B2 (de) | 1979-03-15 |
| DE2025900C3 true DE2025900C3 (de) | 1979-10-31 |
Family
ID=5772247
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2025900A Expired DE2025900C3 (de) | 1970-05-27 | 1970-05-27 | Verfahren zur Herstellung von Polyurethanelastomeren |
Country Status (11)
| Country | Link |
|---|---|
| US (1) | US3794621A (https=) |
| JP (1) | JPS5110279B1 (https=) |
| AT (1) | AT316870B (https=) |
| BE (1) | BE767746A (https=) |
| CA (1) | CA965195A (https=) |
| CH (1) | CH549070A (https=) |
| DE (1) | DE2025900C3 (https=) |
| FR (1) | FR2090331B1 (https=) |
| GB (1) | GB1354523A (https=) |
| NL (1) | NL7107259A (https=) |
| SE (1) | SE378111B (https=) |
Families Citing this family (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3991023A (en) * | 1971-12-07 | 1976-11-09 | Bayer Aktiengesellschaft | Polyurethanes wherein the chain-lengthening agents are benzoic ester diamines |
| US4039514A (en) * | 1972-09-15 | 1977-08-02 | E. I. Du Pont De Nemours And Company | Polyurethanes cured with derivatives of 2,4-diamino-benzamide |
| US4054556A (en) * | 1972-09-15 | 1977-10-18 | E. I. Du Pont De Nemours And Company | Polyurethanes cured with derivatives of 2,4-diamino-benzoic acid |
| DE2301408A1 (de) * | 1973-01-12 | 1974-07-25 | Bayer Ag | Verfahren zur herstellung von harten, ueberwiegend isocyanuratringstrukturen aufweisenden schaumstoffen |
| US4107152A (en) * | 1974-12-17 | 1978-08-15 | Bayer Aktiengesellschaft | Polyurethanes produced from phosphorus containing flame retarding agents which are reactive with isocyanates |
| DE2720166C2 (de) * | 1977-05-05 | 1985-09-19 | Bayer Ag, 5090 Leverkusen | Verfahren zur Herstellung von Polyurethanelastomeren |
| DE2933165A1 (de) * | 1979-08-16 | 1981-03-26 | Bayer Ag, 51373 Leverkusen | Verfahren zur herstellung von dynamisch besonders belastbaren luftreifen |
| DE3405679A1 (de) * | 1984-02-17 | 1985-08-22 | Basf Ag, 6700 Ludwigshafen | Verfahren zur herstellung von gegebenenfalls zelligen polyurethan-polyharnstoff-formkoerpern |
| US4745223A (en) * | 1984-10-11 | 1988-05-17 | Air Products And Chemicals, Inc. | Mono-tertiary-alkylated toluenediamine and derivatives |
| DE3640855A1 (de) * | 1986-11-29 | 1988-06-09 | Bayer Ag | Verfahren zur herstellung von uretdionringen enthaltenden polyurethanen |
| US4810769A (en) * | 1987-06-05 | 1989-03-07 | Air Products And Chemicals, Inc. | Process of preparing polyurethanes cured with 2,6-idaminobenzoic acid derivatives and blends of the 2, 4 and 2,6 isomers |
| US5034426A (en) * | 1987-07-20 | 1991-07-23 | Air Products And Chemicals, Inc. | Aromatic diamine catalytic chain extenders |
| EP0300349A1 (en) * | 1987-07-20 | 1989-01-25 | Air Products And Chemicals, Inc. | Non-fugitive diaminobenzoate catalytic chain extenders |
| US4908394A (en) * | 1987-07-20 | 1990-03-13 | Air Products And Chemicals, Inc. | Diaminobenzoate catalytic chain extenders |
| US4937306A (en) * | 1987-07-20 | 1990-06-26 | Air Products And Chemicals, Inc. | Aromatic diamine catalytic chain extenders |
| US5538679A (en) * | 1988-11-29 | 1996-07-23 | Bayer Aktiengesellschaft | Process of making molded products |
| DE3840167A1 (de) * | 1988-11-29 | 1990-05-31 | Bayer Ag | Verfahren zur herstellung von formkoerpern und die nach diesem verfahren erhaeltlichen formkoerper |
| DE4433437A1 (de) | 1994-09-20 | 1996-03-21 | Bayer Ag | Vernetzer für Textildruck-Bindemittel |
| CN117776942A (zh) * | 2023-12-11 | 2024-03-29 | 清源创新实验室 | 一种基于二硝基苯甲酸制备二氨基苯甲酸的方法 |
-
1970
- 1970-05-27 DE DE2025900A patent/DE2025900C3/de not_active Expired
-
1971
- 1971-04-30 CH CH643671A patent/CH549070A/xx not_active IP Right Cessation
- 1971-05-20 US US00145480A patent/US3794621A/en not_active Expired - Lifetime
- 1971-05-21 GB GB1619171*[A patent/GB1354523A/en not_active Expired
- 1971-05-21 CA CA113,719A patent/CA965195A/en not_active Expired
- 1971-05-26 SE SE7106807A patent/SE378111B/xx unknown
- 1971-05-26 NL NL7107259A patent/NL7107259A/xx unknown
- 1971-05-26 JP JP46035592A patent/JPS5110279B1/ja active Pending
- 1971-05-27 FR FR7119343A patent/FR2090331B1/fr not_active Expired
- 1971-05-27 BE BE767746A patent/BE767746A/xx unknown
- 1971-05-27 AT AT459871A patent/AT316870B/de not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5110279B1 (https=) | 1976-04-02 |
| GB1354523A (en) | 1974-06-05 |
| DE2025900B2 (de) | 1979-03-15 |
| CA965195A (en) | 1975-03-25 |
| CH549070A (de) | 1974-05-15 |
| FR2090331A1 (https=) | 1972-01-14 |
| AT316870B (de) | 1974-07-25 |
| NL7107259A (https=) | 1971-11-30 |
| DE2025900A1 (de) | 1971-12-02 |
| SE378111B (https=) | 1975-08-18 |
| FR2090331B1 (https=) | 1976-03-19 |
| BE767746A (fr) | 1971-10-18 |
| US3794621A (en) | 1974-02-26 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| BI | Miscellaneous see part 2 | ||
| C3 | Grant after two publication steps (3rd publication) | ||
| 8339 | Ceased/non-payment of the annual fee |