GB999123A - New organosilicon compounds and their use - Google Patents
New organosilicon compounds and their useInfo
- Publication number
- GB999123A GB999123A GB8079/64A GB807964A GB999123A GB 999123 A GB999123 A GB 999123A GB 8079/64 A GB8079/64 A GB 8079/64A GB 807964 A GB807964 A GB 807964A GB 999123 A GB999123 A GB 999123A
- Authority
- GB
- United Kingdom
- Prior art keywords
- silane
- diorganopolysiloxane
- composition
- optionally
- inert
- 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
- 150000003961 organosilicon compounds Chemical class 0.000 title 1
- 239000000203 mixture Substances 0.000 abstract 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 abstract 7
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 abstract 6
- -1 hydrocarbon radicals Chemical class 0.000 abstract 6
- 229920005645 diorganopolysiloxane polymer Polymers 0.000 abstract 5
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 abstract 4
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- AYGODUQVENJZAS-UHFFFAOYSA-N ethyl-tri(piperidin-1-yloxy)silane Chemical compound C(C)[Si](ON1CCCCC1)(ON1CCCCC1)ON1CCCCC1 AYGODUQVENJZAS-UHFFFAOYSA-N 0.000 abstract 3
- 239000000377 silicon dioxide Substances 0.000 abstract 3
- 239000004215 Carbon black (E152) Substances 0.000 abstract 2
- XLOMVQKBTHCTTD-UHFFFAOYSA-N Zinc monoxide Chemical compound [Zn]=O XLOMVQKBTHCTTD-UHFFFAOYSA-N 0.000 abstract 2
- 229910000019 calcium carbonate Inorganic materials 0.000 abstract 2
- 235000010216 calcium carbonate Nutrition 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000004205 dimethyl polysiloxane Substances 0.000 abstract 2
- 235000013870 dimethyl polysiloxane Nutrition 0.000 abstract 2
- 125000000623 heterocyclic group Chemical group 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- WOFLNHIWMZYCJH-UHFFFAOYSA-N n-[bis(diethylaminooxy)-methylsilyl]oxy-n-ethylethanamine Chemical compound CCN(CC)O[Si](C)(ON(CC)CC)ON(CC)CC WOFLNHIWMZYCJH-UHFFFAOYSA-N 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 abstract 2
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 abstract 2
- 229920002554 vinyl polymer Polymers 0.000 abstract 2
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 239000000853 adhesive Substances 0.000 abstract 1
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 239000006229 carbon black Substances 0.000 abstract 1
- 239000011248 coating agent Substances 0.000 abstract 1
- 239000008199 coating composition Substances 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000007799 cork Substances 0.000 abstract 1
- 239000011521 glass Substances 0.000 abstract 1
- 125000003106 haloaryl group Chemical group 0.000 abstract 1
- 125000005347 halocycloalkyl group Chemical group 0.000 abstract 1
- 150000005826 halohydrocarbons Chemical class 0.000 abstract 1
- 150000002443 hydroxylamines Chemical class 0.000 abstract 1
- 239000012442 inert solvent Substances 0.000 abstract 1
- YADFUWUAMJZLRK-UHFFFAOYSA-N n-[bis(diethylaminooxy)-phenylsilyl]oxy-n-ethylethanamine Chemical compound CCN(CC)O[Si](ON(CC)CC)(ON(CC)CC)C1=CC=CC=C1 YADFUWUAMJZLRK-UHFFFAOYSA-N 0.000 abstract 1
- 125000000587 piperidin-1-yl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C([H])([H])C1([H])[H] 0.000 abstract 1
- 125000003386 piperidinyl group Chemical group 0.000 abstract 1
- 229920001296 polysiloxane Polymers 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 239000010453 quartz Substances 0.000 abstract 1
- 150000003254 radicals Chemical class 0.000 abstract 1
- 229910000077 silane Inorganic materials 0.000 abstract 1
- 150000004756 silanes Chemical class 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- 239000011787 zinc oxide Substances 0.000 abstract 1
Classifications
-
- 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
- C07F7/0834—Compounds having one or more O-Si linkage
- C07F7/0892—Compounds with a Si-O-N linkage
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/22—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
- C08G77/26—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen nitrogen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/045—Polysiloxanes containing less than 25 silicon 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/16—Polysiloxanes containing silicon bound to oxygen-containing groups to hydroxyl groups
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention comprises (1) organoaminoxysilanes of the formula {R1R11N-O-}3SiR, wherein R, R1 and R11 represent inert, optionally substituted, hydrocarbon radicals, R1 and R11 being optionally joined to form, with the adjacent nitrogen, a heterocyclic ring, and (2) compositions comprising (a) organoaminoxy silanes (1), and (b) a diorganopolysiloxane of the formula HO-(SiR2-O)n-H, wherein n is 5 to 10,000. Specified R, R1 and R11 groups are alkyl, alkenyl, aryl, aralkyl, halocycloalkyl, haloaryl and haloaralkyl. The radical -NR1R11 may, in addition, be pyrrolidin-1-yl, piperidin-1-yl (lower alkyl) piperidinyl, and 4-(lower alkyl) - 1 - piperazinyl. Compounds (1) are prepared by reacting a trihalosilane, Hal3SiR, with 3 moles of a substituted hydroxylamine R1R11NOH, preferably in the presence of an inert solvent and an acid neutralizer, e.g. CaCO3, MgO or a tertiary amine. The composition (2) preferably contains 1 to 10% by weight of the silane based on the diorganopolysiloxane, and is cured by exposure to moisture, optionally in the presence of a catalyst. The composition may contain additives, e.g. inert polysiloxanes, selica, quartz alumina, titania, zinc oxide, calcium carbonate, carbon black, P.V.C., or powdered cork, and may be used in solution, e.g. in aromatic hydrocarbons, halohydrocarbons or aliphatic ethers. The examples describe the preparation of (1) methyltri-(diethylaminoxy) silane, (2) tris-(diethylaminoxy) phenyl silane, and (3) ethyl tri-(piperidine-1-yloxy)-silane; compositions are prepared from methyl tri-(diethylaminoxy) silane and dimethyl polysiloxane both alone, (4) and admixed with silica and an end-blocked low viscosity dimethylpolysiloxane (5), and from (6) ethyl tri-(piperidin-1-yloxy)-silane, silica, titania and a diorganopolysiloxane having methyl and vinyl radicals; the compositions are all cured. Uses: Doping, coating, caulking and adhesives.ALSO:A coating composition comprises (1) an organoaminoxysilanes [R1R11NO-]3SiR in which R, R1 and R11 are inert optionally substituted hydrocarbon radicals, R1 and R11 being optionally joined to form with the adjacent nitrogen a heterocyclic ring, and (2) a diorganopolysiloxane of the formula HO-(SiR2-O-]-H wherein n is 5-10,000. The composition is cured by exposure to air at ambient temperature, optionally in the presence of a catalyst, e.g. amines or organo-tin compounds. In Example 6 glass is coated with a composition comprising ethyl tri(piperidin-1-yloxy)silane, a diorganopolysiloxane containing methyl and vinyl radicals, silica and titania.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR926020A FR1359240A (en) | 1963-02-26 | 1963-02-26 | Organosilicon compounds containing aminoxy groups |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB999123A true GB999123A (en) | 1965-07-21 |
Family
ID=8797890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB8079/64A Expired GB999123A (en) | 1963-02-26 | 1964-02-26 | New organosilicon compounds and their use |
Country Status (7)
| Country | Link |
|---|---|
| BE (1) | BE644376A (en) |
| CH (1) | CH437786A (en) |
| FR (1) | FR1359240A (en) |
| GB (1) | GB999123A (en) |
| LU (1) | LU45514A1 (en) |
| NL (1) | NL142190B (en) |
| SE (1) | SE302362B (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0098911A1 (en) * | 1982-07-13 | 1984-01-25 | Union Carbide Corporation | Improved process for the preparation of oximatohydridosilanes and aminoxyhydridosilanes |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3441583A (en) * | 1965-01-04 | 1969-04-29 | Gen Electric | Aminoxyorganosilicon materials |
| US3484471A (en) * | 1967-12-26 | 1969-12-16 | Gen Electric | Aminoxycyclopolysiloxanes |
-
1963
- 1963-02-26 FR FR926020A patent/FR1359240A/en not_active Expired
-
1964
- 1964-02-24 NL NL646401732A patent/NL142190B/en unknown
- 1964-02-25 LU LU45514A patent/LU45514A1/xx unknown
- 1964-02-25 SE SE2293/64A patent/SE302362B/xx unknown
- 1964-02-25 CH CH229964A patent/CH437786A/en unknown
- 1964-02-26 BE BE644376A patent/BE644376A/xx unknown
- 1964-02-26 GB GB8079/64A patent/GB999123A/en not_active Expired
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0098911A1 (en) * | 1982-07-13 | 1984-01-25 | Union Carbide Corporation | Improved process for the preparation of oximatohydridosilanes and aminoxyhydridosilanes |
Also Published As
| Publication number | Publication date |
|---|---|
| CH437786A (en) | 1967-06-15 |
| FR1359240A (en) | 1964-04-24 |
| BE644376A (en) | 1964-08-26 |
| LU45514A1 (en) | 1964-04-25 |
| NL142190B (en) | 1974-05-15 |
| NL6401732A (en) | 1964-08-27 |
| SE302362B (en) | 1968-07-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US3364160A (en) | Organo-polysiloxane composition convertible at room temperature | |
| CA1219396A (en) | Integrated cross-linkers and scavengers for rtv silicone rubber compositions | |
| EP0104179A1 (en) | Scavengers for one-component alkoxy-functional rtv compositions and processes. | |
| US4499234A (en) | Non-corrosive silicone RTV compositions | |
| GB1273907A (en) | Non-corrosive siloxane vulcanisable at room temperature | |
| JPH03193792A (en) | Composition for accelerating adhesion of curable silicon to substrate | |
| JPS6213452A (en) | Rtv silicone paste having short curing time | |
| US5180771A (en) | Room temperature curable organopolysiloxane composition | |
| GB1064462A (en) | Process for the manufacture of elastomeric cellular sponge and foamed material from organosiloxane polymers | |
| GB1265098A (en) | ||
| US4578492A (en) | Non-corrosive silicone RTV compositions | |
| GB1123729A (en) | Siloxane block co-polymers and the preparation thereof | |
| GB586956A (en) | Improvements in and relating to organo-silicon compounds | |
| US3318898A (en) | Organosilicon compounds and their use | |
| GB1306810A (en) | Preparation of linear halosiloxanes and compounds derived therefrom | |
| GB999123A (en) | New organosilicon compounds and their use | |
| GB971233A (en) | Improvements in or relating to nitrogen-containing organosilicon compounds | |
| GB999847A (en) | Organosiloxane primer compositions and a process for making them | |
| GB1035492A (en) | Organopolysiloxane elastomers | |
| CA1246277A (en) | One-component rtv silicone rubber compositions with good self-bonding properties to acrylate plastics | |
| JPS6241264A (en) | Room temperature curing organopolysiloxane composition | |
| US4644074A (en) | Stabilized organopolysiloxanes and a process for stabilizing the same | |
| JP3149190B2 (en) | Organopolysiloxane materials capable of crosslinking to form elastomers with elimination of alcohol | |
| US3364175A (en) | Polydiorganosiloxanes cured with alkoxysilyl carbamates | |
| GB1083737A (en) | Improvements in substituted silanes |