GB1062418A - New nitrogen-containing siloxanes - Google Patents
New nitrogen-containing siloxanesInfo
- Publication number
- GB1062418A GB1062418A GB3356/64A GB335664A GB1062418A GB 1062418 A GB1062418 A GB 1062418A GB 3356/64 A GB3356/64 A GB 3356/64A GB 335664 A GB335664 A GB 335664A GB 1062418 A GB1062418 A GB 1062418A
- Authority
- GB
- United Kingdom
- Prior art keywords
- siloxanes
- formula
- aminoaryl
- aro
- organosiloxanyl
- 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 nitrogen-containing siloxanes Chemical class 0.000 title abstract 9
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 abstract 3
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 abstract 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 abstract 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 abstract 2
- 125000005001 aminoaryl group Chemical group 0.000 abstract 2
- 150000001875 compounds Chemical class 0.000 abstract 2
- 239000000314 lubricant Substances 0.000 abstract 2
- 238000000034 method Methods 0.000 abstract 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 abstract 2
- 125000004999 nitroaryl group Chemical group 0.000 abstract 2
- 229920001296 polysiloxane Polymers 0.000 abstract 2
- 150000003254 radicals Chemical class 0.000 abstract 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical class C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 abstract 1
- WZJUBBHODHNQPW-UHFFFAOYSA-N 2,4,6,8-tetramethyl-1,3,5,7,2$l^{3},4$l^{3},6$l^{3},8$l^{3}-tetraoxatetrasilocane Chemical compound C[Si]1O[Si](C)O[Si](C)O[Si](C)O1 WZJUBBHODHNQPW-UHFFFAOYSA-N 0.000 abstract 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 1
- 239000007868 Raney catalyst Substances 0.000 abstract 1
- 229910000564 Raney nickel Inorganic materials 0.000 abstract 1
- 125000003545 alkoxy group Chemical group 0.000 abstract 1
- 125000002877 alkyl aryl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 125000004104 aryloxy group Chemical group 0.000 abstract 1
- 229910052799 carbon Inorganic materials 0.000 abstract 1
- 238000010531 catalytic reduction reaction Methods 0.000 abstract 1
- 125000005843 halogen group Chemical group 0.000 abstract 1
- 229910052759 nickel Inorganic materials 0.000 abstract 1
- HMMGMWAXVFQUOA-UHFFFAOYSA-N octamethylcyclotetrasiloxane Chemical compound C[Si]1(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O1 HMMGMWAXVFQUOA-UHFFFAOYSA-N 0.000 abstract 1
- MUMZUERVLWJKNR-UHFFFAOYSA-N oxoplatinum Chemical compound [Pt]=O MUMZUERVLWJKNR-UHFFFAOYSA-N 0.000 abstract 1
- 150000002989 phenols Chemical class 0.000 abstract 1
- 229910003446 platinum oxide Inorganic materials 0.000 abstract 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract 1
- 238000006722 reduction reaction Methods 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 239000010703 silicon Substances 0.000 abstract 1
- 159000000000 sodium salts Chemical class 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M107/00—Lubricating compositions characterised by the base-material being a macromolecular compound
- C10M107/50—Lubricating compositions characterised by the base-material being a macromolecular compound containing silicon
-
- 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
- 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
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M3/00—Liquid compositions essentially based on lubricating components other than mineral lubricating oils or fatty oils and their use as lubricants; Use as lubricants of single liquid substances
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2229/00—Organic macromolecular compounds containing atoms of elements not provided for in groups C10M2205/00, C10M2209/00, C10M2213/00, C10M2217/00, C10M2221/00 or C10M2225/00 as ingredients in lubricant compositions
- C10M2229/04—Siloxanes with specific structure
- C10M2229/05—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon
- C10M2229/052—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen
- C10M2229/0525—Siloxanes with specific structure containing atoms other than silicon, hydrogen, oxygen or carbon containing nitrogen used as base material
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2070/00—Specific manufacturing methods for lubricant compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Photoreceptors In Electrophotography (AREA)
Abstract
Lubricants comprise siloxanes containing the group ArO-CaH2a-Si\sZ, where Ar is an aminoaryl, nitroaryl, aminonitroaryl, or amido-aryl radical, and a is an integer. In Example 3, a lubricant of formula <FORM:1062418/C4-C5/1> is prepared, where n is 1,2,3.ALSO:The invention comprises siloxanes of the formula ArO-CaH2a-Si\sZ, where Ar is an aminoaryl, nitroaryl, aminonitroaryl, or amidoaryl radical and a is an integer. Two of the remaining valency bonds to silicon may be occupied by halogen atoms, alkyl, aryl, aralkyl, alkaryl, alkoxy, aryloxy, or organosiloxanyl groups or substituted derivatives therefrom, the remaining bond being occupied by an organosiloxanyl or substituted organosiloxanyl group. The compounds may be prepared by (1) reacting a sodium salt of a suitably substituted phenol or naphthol with a haloalkyl siloxane or (2) in the case of aminoaryl siloxanes, the reduction of the corresponding nitro product. Such siloxanes may be subsequently copolymerized with one or more organopolysiloxanes. Preferred values for a are 1 to 8 and preferred Ar radicals are amino, nitro, aminonitro or amido phenyl or naphthyl radicals. Haloalkyl siloxanes of method (1) include: bis-1,3 (g -chloropropyl) - tetramethylolisiloxane, 1,3,5,7-tetra (g -iodopropyl) tetramethylcyclotetrasiloxane, and bis - 1,3(g - iodopropyl) - tetramethyldisiloxane. Method (2) may be effected by direct catalytic reduction using e.g. palladium on carbon, platinum oxide on carbon, or Ranye nickel, or by using hydrazine and Raney nickel. The examples prepare a number of compounds of formula: Ar.O(CH2)3 Si Si (CH3)2O. Si (CH3)2.(CH2)3.O.Ar and, by reacting wit octamethylcyclotetrasiloxane, several of the corresponding polysiloxanes of formula: ArO (CH2)3[Si(CH3)2O]n Si(CH3)2(CH2)3.O.Ar are formed, where n is between 104 and 132.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3356/64A GB1062418A (en) | 1964-01-27 | 1964-01-27 | New nitrogen-containing siloxanes |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB3356/64A GB1062418A (en) | 1964-01-27 | 1964-01-27 | New nitrogen-containing siloxanes |
Publications (1)
Publication Number | Publication Date |
---|---|
GB1062418A true GB1062418A (en) | 1967-03-22 |
Family
ID=9756767
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB3356/64A Expired GB1062418A (en) | 1964-01-27 | 1964-01-27 | New nitrogen-containing siloxanes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB1062418A (en) |
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2915072A1 (en) * | 1978-04-26 | 1979-11-08 | M & T Chemicals Inc | PHENOXYALKYL, THIOPHENOXYALKYL AND PYRIDYLOXYALKYLSILANES AND METHOD FOR THEIR PRODUCTION |
EP0014599A2 (en) * | 1979-02-13 | 1980-08-20 | M & T Chemicals, Inc. | Process for the production of silicones |
DE3025034A1 (en) * | 1979-08-08 | 1981-02-26 | M & T Chemicals Inc | SILANES AND METHOD FOR THEIR PRODUCTION |
USRE30677E (en) | 1978-05-17 | 1981-07-14 | M&T Chemicals Inc. | Silicone containing bis-thioether aromatic amines |
EP0054426A2 (en) * | 1980-12-15 | 1982-06-23 | M & T Chemicals, Inc. | Improvements in or relating to siloxanes |
EP0104590A1 (en) * | 1982-09-20 | 1984-04-04 | Kabushiki Kaisha Toshiba | Photocurable silicon compound composition |
US4480009A (en) * | 1980-12-15 | 1984-10-30 | M&T Chemicals Inc. | Siloxane-containing polymers |
US4499149A (en) * | 1980-12-15 | 1985-02-12 | M&T Chemicals Inc. | Siloxane-containing polymers |
WO2018186860A1 (en) * | 2017-04-06 | 2018-10-11 | GE Oil & Gas, Inc. | Absorbent compositions including amino-siloxanes |
-
1964
- 1964-01-27 GB GB3356/64A patent/GB1062418A/en not_active Expired
Cited By (15)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2915072A1 (en) * | 1978-04-26 | 1979-11-08 | M & T Chemicals Inc | PHENOXYALKYL, THIOPHENOXYALKYL AND PYRIDYLOXYALKYLSILANES AND METHOD FOR THEIR PRODUCTION |
US4395527A (en) | 1978-05-17 | 1983-07-26 | M & T Chemicals Inc. | Siloxane-containing polymers |
USRE30677E (en) | 1978-05-17 | 1981-07-14 | M&T Chemicals Inc. | Silicone containing bis-thioether aromatic amines |
EP0014599A2 (en) * | 1979-02-13 | 1980-08-20 | M & T Chemicals, Inc. | Process for the production of silicones |
JPS55129293A (en) * | 1979-02-13 | 1980-10-06 | M & T Chemicals Inc | Functional group contained siloxane and its manufacture |
EP0014599A3 (en) * | 1979-02-13 | 1981-07-01 | M & T Chemicals, Inc. | Silicones and process for their production |
DE3025034A1 (en) * | 1979-08-08 | 1981-02-26 | M & T Chemicals Inc | SILANES AND METHOD FOR THEIR PRODUCTION |
EP0054426A2 (en) * | 1980-12-15 | 1982-06-23 | M & T Chemicals, Inc. | Improvements in or relating to siloxanes |
EP0054426A3 (en) * | 1980-12-15 | 1982-08-11 | M & T Chemicals, Inc. | Improvements in or relating to siloxanes |
US4480009A (en) * | 1980-12-15 | 1984-10-30 | M&T Chemicals Inc. | Siloxane-containing polymers |
US4499149A (en) * | 1980-12-15 | 1985-02-12 | M&T Chemicals Inc. | Siloxane-containing polymers |
JPH0680782A (en) * | 1980-12-15 | 1994-03-22 | M & T Chem Inc | Preparation of siloxane and disiloxane |
JP2589895B2 (en) * | 1980-12-15 | 1997-03-12 | エム・アンド・テイ・ケミカルス・インコーポレイテツド | Siloxane |
EP0104590A1 (en) * | 1982-09-20 | 1984-04-04 | Kabushiki Kaisha Toshiba | Photocurable silicon compound composition |
WO2018186860A1 (en) * | 2017-04-06 | 2018-10-11 | GE Oil & Gas, Inc. | Absorbent compositions including amino-siloxanes |
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