DE2118868A1 - Verfahren zur Herstellung von oxalkylierten Polyamino-1,3,5-triazinen - Google Patents
Verfahren zur Herstellung von oxalkylierten Polyamino-1,3,5-triazinenInfo
- Publication number
- DE2118868A1 DE2118868A1 DE19712118868 DE2118868A DE2118868A1 DE 2118868 A1 DE2118868 A1 DE 2118868A1 DE 19712118868 DE19712118868 DE 19712118868 DE 2118868 A DE2118868 A DE 2118868A DE 2118868 A1 DE2118868 A1 DE 2118868A1
- Authority
- DE
- Germany
- Prior art keywords
- parts
- triazines
- polyamino
- propylene oxide
- melamine
- 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.)
- Pending
Links
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 3
- 150000001408 amides Chemical class 0.000 claims description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims description 12
- 125000002947 alkylene group Chemical group 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 2
- 150000003918 triazines Chemical class 0.000 claims description 2
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 24
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 23
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
- 229920000877 Melamine resin Polymers 0.000 description 17
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 description 16
- 239000011541 reaction mixture Substances 0.000 description 13
- 239000002904 solvent Substances 0.000 description 13
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- -1 alkyl radical Chemical class 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000006227 byproduct Substances 0.000 description 7
- 238000004821 distillation Methods 0.000 description 7
- 239000000203 mixture Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 238000004519 manufacturing process Methods 0.000 description 5
- 239000012299 nitrogen atmosphere Substances 0.000 description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- FIDRAVVQGKNYQK-UHFFFAOYSA-N 1,2,3,4-tetrahydrotriazine Chemical compound C1NNNC=C1 FIDRAVVQGKNYQK-UHFFFAOYSA-N 0.000 description 3
- VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- RFFLAFLAYFXFSW-UHFFFAOYSA-N 1,2-dichlorobenzene Chemical compound ClC1=CC=CC=C1Cl RFFLAFLAYFXFSW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 2
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 2
- 229920005830 Polyurethane Foam Polymers 0.000 description 2
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 230000003472 neutralizing effect Effects 0.000 description 2
- 230000009965 odorless effect Effects 0.000 description 2
- 239000011496 polyurethane foam Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- 238000005303 weighing Methods 0.000 description 2
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- 150000000182 1,3,5-triazines Chemical class 0.000 description 1
- DVVGIUUJYPYENY-UHFFFAOYSA-N 1-methylpyridin-2-one Chemical compound CN1C=CC=CC1=O DVVGIUUJYPYENY-UHFFFAOYSA-N 0.000 description 1
- HTLUPUDQOUYHQS-UHFFFAOYSA-N 2-methyloxirane;1,3,5-triazine-2,4,6-triamine Chemical compound CC1CO1.NC1=NC(N)=NC(N)=N1 HTLUPUDQOUYHQS-UHFFFAOYSA-N 0.000 description 1
- IEFWDQQGFDLKFK-UHFFFAOYSA-N 2-n,2-n-dimethyl-1,3,5-triazine-2,4,6-triamine Chemical compound CN(C)C1=NC(N)=NC(N)=N1 IEFWDQQGFDLKFK-UHFFFAOYSA-N 0.000 description 1
- PUNBNIKEWSXOSK-UHFFFAOYSA-N 6-octadecyl-1,3,5-triazine-2,4-diamine Chemical compound C(CCCCCCCCCCCCCCCCC)C1=NC(=NC(=N1)N)N PUNBNIKEWSXOSK-UHFFFAOYSA-N 0.000 description 1
- GZVHEAJQGPRDLQ-UHFFFAOYSA-N 6-phenyl-1,3,5-triazine-2,4-diamine Chemical compound NC1=NC(N)=NC(C=2C=CC=CC=2)=N1 GZVHEAJQGPRDLQ-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-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
- APJJQIXJONEBHW-UHFFFAOYSA-N N,N-dimethylformamide 1,3,5-triazine-2,4,6-triamine Chemical compound C(=O)N(C)C.N1=C(N)N=C(N)N=C1N APJJQIXJONEBHW-UHFFFAOYSA-N 0.000 description 1
- SUAKHGWARZSWIH-UHFFFAOYSA-N N,N‐diethylformamide Chemical compound CCN(CC)C=O SUAKHGWARZSWIH-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- AWMVMTVKBNGEAK-UHFFFAOYSA-N Styrene oxide Chemical compound C1OC1C1=CC=CC=C1 AWMVMTVKBNGEAK-UHFFFAOYSA-N 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- GHVZOJONCUEWAV-UHFFFAOYSA-N [K].CCO Chemical compound [K].CCO GHVZOJONCUEWAV-UHFFFAOYSA-N 0.000 description 1
- 150000008043 acidic salts Chemical class 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910001854 alkali hydroxide Inorganic materials 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000004703 alkoxides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- AJFDBNQQDYLMJN-UHFFFAOYSA-N n,n-diethylacetamide Chemical compound CCN(CC)C(C)=O AJFDBNQQDYLMJN-UHFFFAOYSA-N 0.000 description 1
- YKOQQFDCCBKROY-UHFFFAOYSA-N n,n-diethylpropanamide Chemical compound CCN(CC)C(=O)CC YKOQQFDCCBKROY-UHFFFAOYSA-N 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- BDAWXSQJJCIFIK-UHFFFAOYSA-N potassium methoxide Chemical compound [K+].[O-]C BDAWXSQJJCIFIK-UHFFFAOYSA-N 0.000 description 1
- AWDMDDKZURRKFG-UHFFFAOYSA-N potassium;propan-1-olate Chemical compound [K+].CCC[O-] AWDMDDKZURRKFG-UHFFFAOYSA-N 0.000 description 1
- WQKGAJDYBZOFSR-UHFFFAOYSA-N potassium;propan-2-olate Chemical compound [K+].CC(C)[O-] WQKGAJDYBZOFSR-UHFFFAOYSA-N 0.000 description 1
- 150000003254 radicals Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
- SYXYWTXQFUUWLP-UHFFFAOYSA-N sodium;butan-1-olate Chemical compound [Na+].CCCC[O-] SYXYWTXQFUUWLP-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000011877 solvent mixture Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 150000004072 triols Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 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
- C07D251/40—Nitrogen atoms
- C07D251/54—Three nitrogen atoms
- C07D251/70—Other substituted melamines
-
- 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
- Y10S521/902—Cellular polymer containing an isocyanurate structure
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Polyethers (AREA)
Priority Applications (7)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712118868 DE2118868A1 (de) | 1971-04-19 | 1971-04-19 | Verfahren zur Herstellung von oxalkylierten Polyamino-1,3,5-triazinen |
| US24347672 US3812122A (en) | 1971-04-19 | 1972-04-12 | Process for making oxyalkylated polyamino-1,3,5-triazines |
| NL7205140A NL7205140A (enExample) | 1971-04-19 | 1972-04-17 | |
| GB1777072A GB1380958A (en) | 1971-04-19 | 1972-04-18 | Production of oxyalkylated polyamino -1,3,5-triazines |
| FR7213582A FR2144214A5 (enExample) | 1971-04-19 | 1972-04-18 | |
| BE782261A BE782261A (fr) | 1971-04-19 | 1972-04-18 | Procede de preparation de produits d'addition d'oxydes d'alkylene sur des polyamino-1,3,5-triazines |
| IT49723/72A IT954450B (it) | 1971-04-19 | 1972-04-18 | Procedimento per la produzione di poliammino 1 3 5 triazine ossialchilate |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19712118868 DE2118868A1 (de) | 1971-04-19 | 1971-04-19 | Verfahren zur Herstellung von oxalkylierten Polyamino-1,3,5-triazinen |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2118868A1 true DE2118868A1 (de) | 1972-10-26 |
Family
ID=5805106
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19712118868 Pending DE2118868A1 (de) | 1971-04-19 | 1971-04-19 | Verfahren zur Herstellung von oxalkylierten Polyamino-1,3,5-triazinen |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US3812122A (enExample) |
| BE (1) | BE782261A (enExample) |
| DE (1) | DE2118868A1 (enExample) |
| FR (1) | FR2144214A5 (enExample) |
| GB (1) | GB1380958A (enExample) |
| IT (1) | IT954450B (enExample) |
| NL (1) | NL7205140A (enExample) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0161424A1 (de) * | 1984-03-31 | 1985-11-21 | BASF Aktiengesellschaft | Verfahren zur Herstellung von s-Triazinreste enthaltenden Polyether-polyolmischungen |
| DE10136321C1 (de) * | 2001-07-26 | 2002-12-12 | Agrolinz Melamin Gmbh Linz | Polymere aus Triazinderivaten |
| EP1279669A3 (de) * | 2001-07-26 | 2003-12-10 | Agrolinz Melamin GmbH | Polyalkylenoxid-freie Gemische aus Triazinderivaten |
| WO2008022918A3 (de) * | 2006-08-23 | 2008-04-10 | Basf Ag | Verbindungen und ihre verwendung zur herstellung von leder und als dispergiermittel |
| EP2128144A1 (en) | 2008-05-30 | 2009-12-02 | Basf Se | Amphiphilic molecules with a triazine core |
| WO2009144274A3 (en) * | 2008-05-30 | 2010-05-14 | Basf Se | Amphiphilic molecules with a triazine core |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CH566294A5 (enExample) * | 1972-03-28 | 1975-09-15 | Ciba Geigy Ag | |
| US20040259967A1 (en) * | 2003-04-23 | 2004-12-23 | Neill Paul L. | Liquid hardness agent for open cell foams |
| WO2007047661A2 (en) * | 2005-10-18 | 2007-04-26 | Stepan Company | Prepolymer containing a liquid hardness agent for open cell foams |
| HUE032826T2 (en) | 2010-08-05 | 2017-11-28 | Basf Se | Process for the preparation of amino triazine alkoxylates |
| WO2021067553A1 (en) * | 2019-10-04 | 2021-04-08 | INVISTA North America S.à r.l. | Guanamines and bis-guanamines useful in polyols and foams |
| CN111363135B (zh) * | 2020-03-14 | 2022-11-08 | 浙江恒丰新材料有限公司 | 一种三聚氰胺-环氧乙烷/环氧丙烷共聚物聚醚多元醇的制备方法及应用 |
-
1971
- 1971-04-19 DE DE19712118868 patent/DE2118868A1/de active Pending
-
1972
- 1972-04-12 US US24347672 patent/US3812122A/en not_active Expired - Lifetime
- 1972-04-17 NL NL7205140A patent/NL7205140A/xx unknown
- 1972-04-18 GB GB1777072A patent/GB1380958A/en not_active Expired
- 1972-04-18 FR FR7213582A patent/FR2144214A5/fr not_active Expired
- 1972-04-18 BE BE782261A patent/BE782261A/xx unknown
- 1972-04-18 IT IT49723/72A patent/IT954450B/it active
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0161424A1 (de) * | 1984-03-31 | 1985-11-21 | BASF Aktiengesellschaft | Verfahren zur Herstellung von s-Triazinreste enthaltenden Polyether-polyolmischungen |
| DE10136321C1 (de) * | 2001-07-26 | 2002-12-12 | Agrolinz Melamin Gmbh Linz | Polymere aus Triazinderivaten |
| EP1279669A3 (de) * | 2001-07-26 | 2003-12-10 | Agrolinz Melamin GmbH | Polyalkylenoxid-freie Gemische aus Triazinderivaten |
| US6818726B2 (en) | 2001-07-26 | 2004-11-16 | Agrolinz Melamin Gmbh | Polymers from hydroxyalkyl amino triazines and polyfunctional compounds |
| US6818768B2 (en) | 2001-07-26 | 2004-11-16 | Agrolinz Melamin Gmbh | Mixtures of triazine derivatives free from polyalkylene oxide |
| WO2008022918A3 (de) * | 2006-08-23 | 2008-04-10 | Basf Ag | Verbindungen und ihre verwendung zur herstellung von leder und als dispergiermittel |
| US8211550B2 (en) | 2006-08-23 | 2012-07-03 | Basf Se | Compounds and their use for producing leather and as dispersants |
| EP2128144A1 (en) | 2008-05-30 | 2009-12-02 | Basf Se | Amphiphilic molecules with a triazine core |
| WO2009144274A3 (en) * | 2008-05-30 | 2010-05-14 | Basf Se | Amphiphilic molecules with a triazine core |
| CN102046611A (zh) * | 2008-05-30 | 2011-05-04 | 巴斯夫欧洲公司 | 具有三嗪核的两亲性分子 |
Also Published As
| Publication number | Publication date |
|---|---|
| FR2144214A5 (enExample) | 1973-02-09 |
| BE782261A (fr) | 1972-10-18 |
| US3812122A (en) | 1974-05-21 |
| GB1380958A (en) | 1975-01-22 |
| NL7205140A (enExample) | 1972-10-23 |
| IT954450B (it) | 1973-08-30 |
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