DE2737211A1 - Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendung - Google Patents
Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendungInfo
- Publication number
- DE2737211A1 DE2737211A1 DE19772737211 DE2737211A DE2737211A1 DE 2737211 A1 DE2737211 A1 DE 2737211A1 DE 19772737211 DE19772737211 DE 19772737211 DE 2737211 A DE2737211 A DE 2737211A DE 2737211 A1 DE2737211 A1 DE 2737211A1
- Authority
- DE
- Germany
- Prior art keywords
- isocyanurate
- isocyanate
- weight
- free
- distillation
- 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.)
- Granted
Links
- 239000003054 catalyst Substances 0.000 title claims abstract description 25
- 239000012948 isocyanate Substances 0.000 title claims abstract description 8
- 150000002513 isocyanates Chemical class 0.000 title claims abstract description 6
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical group OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 claims abstract description 24
- 125000005442 diisocyanate group Chemical group 0.000 claims abstract description 16
- 229920001228 polyisocyanate Polymers 0.000 claims abstract description 8
- 239000005056 polyisocyanate Substances 0.000 claims abstract description 8
- 239000000853 adhesive Substances 0.000 claims abstract description 3
- 230000001070 adhesive effect Effects 0.000 claims abstract description 3
- 229920003052 natural elastomer Polymers 0.000 claims abstract description 3
- 229920001194 natural rubber Polymers 0.000 claims abstract description 3
- 239000004814 polyurethane Substances 0.000 claims abstract description 3
- 229920002635 polyurethane Polymers 0.000 claims abstract description 3
- 229920003051 synthetic elastomer Polymers 0.000 claims abstract description 3
- 239000005061 synthetic rubber Substances 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 27
- 238000005829 trimerization reaction Methods 0.000 claims description 21
- 239000011541 reaction mixture Substances 0.000 claims description 13
- 238000004821 distillation Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 3
- 230000003197 catalytic effect Effects 0.000 claims description 3
- 230000000996 additive effect Effects 0.000 claims description 2
- 238000009835 boiling Methods 0.000 claims description 2
- 239000007788 liquid Substances 0.000 claims description 2
- 239000003973 paint Substances 0.000 claims description 2
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 claims description 2
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims 1
- 239000002574 poison Substances 0.000 abstract description 8
- 231100000614 poison Toxicity 0.000 abstract description 8
- 230000009849 deactivation Effects 0.000 abstract description 5
- 238000006243 chemical reaction Methods 0.000 abstract description 3
- 239000004922 lacquer Substances 0.000 abstract 1
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 35
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 19
- RREANTFLPGEWEN-MBLPBCRHSA-N 7-[4-[[(3z)-3-[4-amino-5-[(3,4,5-trimethoxyphenyl)methyl]pyrimidin-2-yl]imino-5-fluoro-2-oxoindol-1-yl]methyl]piperazin-1-yl]-1-cyclopropyl-6-fluoro-4-oxoquinoline-3-carboxylic acid Chemical compound COC1=C(OC)C(OC)=CC(CC=2C(=NC(\N=C/3C4=CC(F)=CC=C4N(CN4CCN(CC4)C=4C(=CC=5C(=O)C(C(O)=O)=CN(C=5C=4)C4CC4)F)C\3=O)=NC=2)N)=C1 RREANTFLPGEWEN-MBLPBCRHSA-N 0.000 description 10
- 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 10
- 150000002989 phenols Chemical class 0.000 description 7
- 150000001299 aldehydes Chemical class 0.000 description 5
- 230000007717 exclusion Effects 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- SIKJAQJRHWYJAI-UHFFFAOYSA-N Indole Chemical compound C1=CC=C2NC=CC2=C1 SIKJAQJRHWYJAI-UHFFFAOYSA-N 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- -1 amino-benzyl group Chemical group 0.000 description 4
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 4
- 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 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- PZOUSPYUWWUPPK-UHFFFAOYSA-N indole Natural products CC1=CC=CC2=C1C=CN2 PZOUSPYUWWUPPK-UHFFFAOYSA-N 0.000 description 2
- RKJUIXBNRJVNHR-UHFFFAOYSA-N indolenine Natural products C1=CC=C2CC=NC2=C1 RKJUIXBNRJVNHR-UHFFFAOYSA-N 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- BGJSXRVXTHVRSN-UHFFFAOYSA-N 1,3,5-trioxane Chemical compound C1OCOCO1 BGJSXRVXTHVRSN-UHFFFAOYSA-N 0.000 description 1
- ZMSQRSUTMFYPLQ-UHFFFAOYSA-N 2-(8-methylnonyl)phenol Chemical class CC(C)CCCCCCCC1=CC=CC=C1O ZMSQRSUTMFYPLQ-UHFFFAOYSA-N 0.000 description 1
- WJQOZHYUIDYNHM-UHFFFAOYSA-N 2-tert-Butylphenol Chemical class CC(C)(C)C1=CC=CC=C1O WJQOZHYUIDYNHM-UHFFFAOYSA-N 0.000 description 1
- GZFGOTFRPZRKDS-UHFFFAOYSA-N 4-bromophenol Chemical compound OC1=CC=C(Br)C=C1 GZFGOTFRPZRKDS-UHFFFAOYSA-N 0.000 description 1
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 1
- 238000006683 Mannich reaction Methods 0.000 description 1
- QCOGKXLOEWLIDC-UHFFFAOYSA-N N-methylbutylamine Chemical compound CCCCNC QCOGKXLOEWLIDC-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-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
- 125000001246 bromo group Chemical group Br* 0.000 description 1
- 238000006555 catalytic reaction Methods 0.000 description 1
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical class OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/26—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hetero atoms directly attached to ring carbon atoms
- C07D251/30—Only oxygen atoms
- C07D251/34—Cyanuric or isocyanuric esters
-
- 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
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
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)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772737211 DE2737211A1 (de) | 1977-08-18 | 1977-08-18 | Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendung |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19772737211 DE2737211A1 (de) | 1977-08-18 | 1977-08-18 | Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendung |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2737211A1 true DE2737211A1 (de) | 1979-03-01 |
| DE2737211C2 DE2737211C2 (enrdf_load_stackoverflow) | 1990-09-06 |
Family
ID=6016693
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772737211 Granted DE2737211A1 (de) | 1977-08-18 | 1977-08-18 | Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendung |
Country Status (1)
| Country | Link |
|---|---|
| DE (1) | DE2737211A1 (enrdf_load_stackoverflow) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039864A1 (de) * | 1980-05-13 | 1981-11-18 | Bayer Ag | Neue Isocyanato-isocyanurate, ein Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Isocyanat-Komponente in Polyurethan-Lacken |
| EP0416338A3 (en) * | 1989-08-29 | 1991-09-04 | Bayer Ag | Process for the preparation of solutio2s of polyisocyanates containing isocyanurate groups in solvents for lacquers and their use |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325826A1 (de) * | 1973-05-22 | 1974-12-19 | Veba Chemie Ag | Lagerstabile polyisocyanate und deren herstellung |
-
1977
- 1977-08-18 DE DE19772737211 patent/DE2737211A1/de active Granted
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2325826A1 (de) * | 1973-05-22 | 1974-12-19 | Veba Chemie Ag | Lagerstabile polyisocyanate und deren herstellung |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0039864A1 (de) * | 1980-05-13 | 1981-11-18 | Bayer Ag | Neue Isocyanato-isocyanurate, ein Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Isocyanat-Komponente in Polyurethan-Lacken |
| EP0416338A3 (en) * | 1989-08-29 | 1991-09-04 | Bayer Ag | Process for the preparation of solutio2s of polyisocyanates containing isocyanurate groups in solvents for lacquers and their use |
| JPH06102709B2 (ja) | 1989-08-29 | 1994-12-14 | バイエル・アクチエンゲゼルシヤフト | イソシアヌレートポリイソシアネートを含有する組成物の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| DE2737211C2 (enrdf_load_stackoverflow) | 1990-09-06 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE1667309C3 (de) | Verfahren zur Herstellung von Isocyanattrimere!! | |
| DE2551634B2 (de) | Verfahren zur Herstellung von Isocyanuratgruppen aufweisenden Polyisocyanaten | |
| EP0017998A1 (de) | Verfahren zur kontinuierlichen Herstellung von Isocyanuratgruppen enhaltenden (cyclo)-aliphatischen Polyisocyanaten | |
| DE1215365B (de) | Verfahren zur Herstellung von hoehermolekularen Polyisocyanaten mit Biuret-Struktur | |
| DE3144672A1 (de) | Verfahren zur herstellung von mischtrimerisaten organischer isocyanate, die nach dem verfahren erhaltenen mischtrimerisate, sowie ihre verwendung zur herstellung von polyurethanen | |
| DE2452532A1 (de) | Verfahren zur herstellung von polyisocyanaten mit isocyanurat-struktur | |
| WO2007077058A1 (de) | Ionische flüssigkeiten enthaltene harze | |
| EP0193828A1 (de) | Isocyanuratgruppen aufweisende Polyisocyanate, ein Verfahren zu ihrer Herstellung und ihre Verwendung als Isocyanatkomponente in Polyurethanlacken | |
| DE1694214A1 (de) | Kunststoffe aus Isocyanatbasis und Verfahren zu ihrer Herstellung | |
| DE2342603B2 (de) | Verfahren zur Herstellung von Malonsäuredialkylesterblockierten Biuretpolyisocyanaten sowie deren Verwendung | |
| DE2534559A1 (de) | Verfahren zur herstellung kernalkylierter mehrkernphenole und ihre verwendung | |
| EP0082987B1 (de) | Neue Isocyanato-isocyanurate sowie ein Verfahren zu deren Herstellung | |
| DE1158492B (de) | Verfahren zur Herstellung von Urethanen | |
| DE2737211A1 (de) | Verfahren zur herstellung von polyisocyanaten mit isocyanuratstruktur sowie ihre verwendung | |
| DE2254930A1 (de) | Hexahydrotriazin-addukt und verfahren zu dessen herstellung | |
| DE1568494A1 (de) | Verfahren zur Herstellung von Mono- und Polycetessigsaeureestern | |
| DE2005693A1 (en) | Methylene-n-arylurethane-n'-amido cpds for cross-linking pol - with hydroxyl gps | |
| DE3610198A1 (de) | Polyisocyanat-zubereitungen, ein verfahren zu ihrer herstellung und ihrer verwendung zur herstellung von polyurethan-kunststoffen oder als lufttrocknende beschichtungs- oder klebemittel | |
| DE2166502C3 (de) | Verfahren zur Herstellung von neuen Enamingruppen enthaltenden Prepolymeren und ihre Verwendung | |
| DE3135065A1 (de) | N,n,n'-trimethyl-n'-2-hydroxyethyl-propylendiamin, verfahren zu seiner herstellung, polyurethane, die 0,01 bis 5 gew.-% n,n,n'-trimethyl-n'-2-hydroxyethyl-propylendiamin enthalten und seine verwendung als katalysator | |
| DE69224495T2 (de) | Verfahren zur selektiven Herstellung von 4,4-Methylen-bis-(N-phenylalkylcarbamate) | |
| DE2855505C3 (de) | Verfahren zur Herstellung von 2-Methylen-aldehyden | |
| DE3420923A1 (de) | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten, die nach diesem verfahren erhaeltlichen verbindungen und ihre verwendung zur herstellung von polyurethanen | |
| EP0082973B1 (de) | Neue biuretgruppenhaltige Polyisocyanate sowie ein Verfahren zu deren Herstellung | |
| EP0039864A1 (de) | Neue Isocyanato-isocyanurate, ein Verfahren zu ihrer Herstellung, sowie ihre Verwendung als Isocyanat-Komponente in Polyurethan-Lacken |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OD | Request for examination | ||
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2641380 Format of ref document f/p: P |
|
| 8176 | Proceedings suspended because of application no: |
Ref document number: 2641380 Country of ref document: DE Format of ref document f/p: P |
|
| 8178 | Suspension cancelled | ||
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2641380 Format of ref document f/p: P |
|
| AF | Is addition to no. |
Ref country code: DE Ref document number: 2641380 Format of ref document f/p: P |
|
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition | ||
| 8340 | Patent of addition ceased/non-payment of fee of main patent |