GB1120859A - Organo-aminomethyl-silicon compounds - Google Patents
Organo-aminomethyl-silicon compoundsInfo
- Publication number
- GB1120859A GB1120859A GB47285/66A GB4728566A GB1120859A GB 1120859 A GB1120859 A GB 1120859A GB 47285/66 A GB47285/66 A GB 47285/66A GB 4728566 A GB4728566 A GB 4728566A GB 1120859 A GB1120859 A GB 1120859A
- Authority
- GB
- United Kingdom
- Prior art keywords
- dimethyl
- carbon atoms
- radical
- alkyl
- amine
- 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
- -1 aralkyl radicals Chemical class 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 abstract 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 abstract 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 abstract 2
- 125000003277 amino group Chemical group 0.000 abstract 2
- 238000006243 chemical reaction Methods 0.000 abstract 2
- 239000012442 inert solvent Substances 0.000 abstract 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N monobenzene Natural products C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 2
- 150000003335 secondary amines Chemical class 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 abstract 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- OZAMSKAOXGIEME-UHFFFAOYSA-N bromomethyl-butoxy-dimethylsilane Chemical compound C[Si](OCCCC)(CBr)C OZAMSKAOXGIEME-UHFFFAOYSA-N 0.000 abstract 1
- SGEIZEOCYMDFJP-UHFFFAOYSA-N bromomethyl-methoxy-dimethylsilane Chemical compound CO[Si](C)(C)CBr SGEIZEOCYMDFJP-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- IGMQAYXTTRYCPZ-UHFFFAOYSA-N chloromethyl-ethoxy-dimethylsilane Chemical compound CCO[Si](C)(C)CCl IGMQAYXTTRYCPZ-UHFFFAOYSA-N 0.000 abstract 1
- 125000000753 cycloalkyl group Chemical group 0.000 abstract 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 abstract 1
- WEHWNAOGRSTTBQ-UHFFFAOYSA-N dipropylamine Chemical compound CCCNCCC WEHWNAOGRSTTBQ-UHFFFAOYSA-N 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 125000005842 heteroatom Chemical group 0.000 abstract 1
- 125000000623 heterocyclic group Chemical group 0.000 abstract 1
- 239000012433 hydrogen halide Substances 0.000 abstract 1
- 229910000039 hydrogen halide Inorganic materials 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 230000003301 hydrolyzing effect Effects 0.000 abstract 1
- RIWRFSMVIUAEBX-UHFFFAOYSA-N n-methyl-1-phenylmethanamine Chemical compound CNCC1=CC=CC=C1 RIWRFSMVIUAEBX-UHFFFAOYSA-N 0.000 abstract 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 abstract 1
- 239000011496 polyurethane foam Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 239000007858 starting material Substances 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- ORGHESHFQPYLAO-UHFFFAOYSA-N vinyl radical Chemical compound C=[CH] ORGHESHFQPYLAO-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 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
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
- C08G18/1883—Catalysts containing secondary or tertiary amines or salts thereof having heteroatoms other than oxygen and nitrogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0838—Compounds with one or more Si-O-Si sequences
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
- C07F7/02—Silicon compounds
- C07F7/08—Compounds having one or more C—Si linkages
- C07F7/18—Compounds having one or more C—Si linkages as well as one or more C—O—Si linkages
- C07F7/1804—Compounds having Si-O-C linkages
- C07F7/1872—Preparation; Treatments not provided for in C07F7/20
- C07F7/1892—Preparation; Treatments not provided for in C07F7/20 by reactions not provided for in C07F7/1876 - C07F7/1888
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Silicon Polymers (AREA)
Abstract
Novel compounds having the general formula R1R11NCH2Si(CH3)2O-Q wherein R1 and R11 can be the same or different and are each substituted or unsubstituted alkyl, cycloalkyl, alkenyl or aralkyl radicals of 1 to 8 carbon atoms or taken together with N can form a saturated heterocyclic ring with optional presence of other hetero atoms, and Q is an alkyl radical of 1 to 4 carbon atoms or a radical having the general formula -[YY1Si-O]nSi(CH3)2-CH2 -NR1R11 wherein Y and Y1 are each alkyl radicals of 1 to 8 carbon atoms or phenyl or a vinyl radical and n is 0 to 4 are prepared by reacting in an inert solvent a dimethyl-(halomethyl)-alkoxysilane X-CH2-Si(CH3)2-OR wherein X is Cl or Br and R is an alkyl radical of 1 to 4 carbon atoms with a secondary amine R1-NH-R11, and either isolating the resulting aminosubstituted organoalkoxysilane, or hydrolysing it with water or aqueous alkali metal hydroxide to form the siloxane. The inert solvent is preferably benzene or toluene, and the reaction may also be carried out in the presence of a tertiary amine to find the hydrogen halide released by the reaction. Before the hydrolysis step, a difunctional diorgano-silane YY1SiZ2, wherein Z is Cl or OR, may be mixed with the amino-substituted organoalkoxysilane. Preferred secondary amines HNR1R11 include dimethylamine, diethylamine, di-n-propylamine, N - methylcyclohexylamine, diallylamine, N-methylbenzylamine, bis - (b - trimethylsiloxyethyl)-amine, pyrrolidine, piperidine, morpholine and N-(b -hydroxyethyl)-piperazine. Preferred silane starting materials are dimethyl-(bromomethyl) - methoxysilane, dimethyl-(chloromethyl) - ethoxysilane and dimethyl-(bromomethyl)-n-butoxysilane. Also exemplified as a product of the invention is a compound of the formula (HO-CH2-CH2)2N-CH2-[Si(CH3) 2-O]p-Si(CH3)2 -CH2-N(CH2-CH2OH)2, where p is less than or equal to 5. The compounds of the invention may be used as catalysts for the production of polyurethane foams.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF47643A DE1244181B (en) | 1965-11-11 | 1965-11-11 | Process for the preparation of terminally aminomethyl-substituted diorganosiloxanes |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1120859A true GB1120859A (en) | 1968-07-24 |
Family
ID=7101755
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB47285/66A Expired GB1120859A (en) | 1965-11-11 | 1966-10-21 | Organo-aminomethyl-silicon compounds |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE689587A (en) |
| DE (1) | DE1244181B (en) |
| GB (1) | GB1120859A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004067605A1 (en) * | 2003-01-30 | 2004-08-12 | Consortium für elektrochemische Industrie GmbH | Aminomethylene functional siloxanes |
| CN116874521A (en) * | 2023-07-17 | 2023-10-13 | 东莞长联新材料科技股份有限公司 | A kind of tackifier, polyurethane self-adhesive screen printing silica gel and its preparation method and application |
| CN120025547A (en) * | 2025-04-23 | 2025-05-23 | 山东东岳有机硅材料股份有限公司 | Side chain amino silicone oil and preparation method thereof |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE102007016990A1 (en) * | 2007-04-11 | 2008-10-16 | Wacker Chemie Ag | Methylol-containing siloxanes |
-
1965
- 1965-11-11 DE DEF47643A patent/DE1244181B/en active Pending
-
1966
- 1966-10-21 GB GB47285/66A patent/GB1120859A/en not_active Expired
- 1966-11-10 BE BE689587D patent/BE689587A/xx unknown
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2004067605A1 (en) * | 2003-01-30 | 2004-08-12 | Consortium für elektrochemische Industrie GmbH | Aminomethylene functional siloxanes |
| CN116874521A (en) * | 2023-07-17 | 2023-10-13 | 东莞长联新材料科技股份有限公司 | A kind of tackifier, polyurethane self-adhesive screen printing silica gel and its preparation method and application |
| CN120025547A (en) * | 2025-04-23 | 2025-05-23 | 山东东岳有机硅材料股份有限公司 | Side chain amino silicone oil and preparation method thereof |
Also Published As
| Publication number | Publication date |
|---|---|
| BE689587A (en) | 1967-04-14 |
| DE1244181B (en) | 1967-07-13 |
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