GB786452A - Improvements in or relating to organosilicon compounds - Google Patents
Improvements in or relating to organosilicon compoundsInfo
- Publication number
- GB786452A GB786452A GB25645/55A GB2564555A GB786452A GB 786452 A GB786452 A GB 786452A GB 25645/55 A GB25645/55 A GB 25645/55A GB 2564555 A GB2564555 A GB 2564555A GB 786452 A GB786452 A GB 786452A
- Authority
- GB
- United Kingdom
- Prior art keywords
- hcl
- carbon atoms
- hydrocarbon radical
- radical containing
- mesi
- 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
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 abstract 10
- 239000004215 Carbon black (E152) Substances 0.000 abstract 10
- 229930195733 hydrocarbon Natural products 0.000 abstract 10
- 125000004432 carbon atom Chemical group C* 0.000 abstract 9
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 9
- -1 wool Polymers 0.000 abstract 8
- 239000007864 aqueous solution Substances 0.000 abstract 4
- 239000011521 glass Substances 0.000 abstract 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 abstract 3
- 229910052801 chlorine Inorganic materials 0.000 abstract 3
- 125000001309 chloro group Chemical group Cl* 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 229910052739 hydrogen Inorganic materials 0.000 abstract 3
- 239000001257 hydrogen Substances 0.000 abstract 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- 229920001296 polysiloxane Polymers 0.000 abstract 3
- 150000003839 salts Chemical class 0.000 abstract 3
- 229910000077 silane Inorganic materials 0.000 abstract 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 abstract 2
- 229920000742 Cotton Polymers 0.000 abstract 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 2
- 239000004677 Nylon Substances 0.000 abstract 2
- 229920000297 Rayon Polymers 0.000 abstract 2
- 125000003545 alkoxy group Chemical group 0.000 abstract 2
- 239000002184 metal Substances 0.000 abstract 2
- 229920001778 nylon Polymers 0.000 abstract 2
- 239000004033 plastic Substances 0.000 abstract 2
- 229920003023 plastic Polymers 0.000 abstract 2
- 239000002964 rayon Substances 0.000 abstract 2
- 239000005871 repellent Substances 0.000 abstract 2
- 150000004756 silanes Chemical class 0.000 abstract 2
- 239000002023 wood Substances 0.000 abstract 2
- 210000002268 wool Anatomy 0.000 abstract 2
- 229910004373 HOAc Inorganic materials 0.000 abstract 1
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 1
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 abstract 1
- 125000003342 alkenyl group Chemical group 0.000 abstract 1
- 125000000217 alkyl group Chemical group 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 150000001414 amino alcohols 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
- 239000005357 flat glass Substances 0.000 abstract 1
- 239000003365 glass fiber Substances 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 239000003960 organic solvent Substances 0.000 abstract 1
- 239000000123 paper Substances 0.000 abstract 1
- 239000003208 petroleum Substances 0.000 abstract 1
- 238000006748 scratching Methods 0.000 abstract 1
- 230000002393 scratching effect Effects 0.000 abstract 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical class [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 abstract 1
- 238000004513 sizing Methods 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 239000002904 solvent Substances 0.000 abstract 1
- 239000004753 textile Substances 0.000 abstract 1
- ZQTYRTSKQFQYPQ-UHFFFAOYSA-N trisiloxane Chemical compound [SiH3]O[SiH2]O[SiH3] ZQTYRTSKQFQYPQ-UHFFFAOYSA-N 0.000 abstract 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/4922—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane
- C04B41/4944—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as monomers, i.e. as organosilanes RnSiX4-n, e.g. alkyltrialkoxysilane, dialkyldialkoxysilane containing atoms other than carbon, hydrogen, oxygen, silicon, alkali metals or halogens, e.g. N-silyldisilazane: Image
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C25/00—Surface treatment of fibres or filaments made from glass, minerals or slags
- C03C25/10—Coating
- C03C25/24—Coatings containing organic materials
- C03C25/40—Organo-silicon compounds
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/495—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers
- C04B41/4961—Polyorganosiloxanes, i.e. polymers with a Si-O-Si-O-chain; "silicones"
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Ceramic Engineering (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Structural Engineering (AREA)
- General Life Sciences & Earth Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Geochemistry & Mineralogy (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
A composition for sizing glass fibres or for treating cotton, wool, nylon, rayon and acrylonitrile fibres comprises an aqueous solution of a salt of an aminoalkoxy silane of the formula RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof (i.e. polysiloxane), where R is a monovalent hydrocarbon radical, a hydrogen atom or an alkoxy group, at least one R being a hydrocarbon radical, n is from 1 to 3, R11 is hydrogen or a methyl group, R1 is a hydrocarbon radical containing less than 11 carbon atoms, a hydrogen atom or a hydroxy-alkyl radical containing 2 or 3 carbon atoms, and Y is a chlorine atom or an acyloxy radical containing less than 4 carbon atoms. The solutions may be stabilized by addition of acetic acid to a pH of about 6. Specifications 654,450, [Group IV (b)], and 686,068 are referred to.ALSO:A composition for treating glass and other surfaces to render them water-repellent or to act as a lubricant comprises a salt of an aminoalkoxy silane of the formula RnSi(OCHR11CH2NR12.HY)4-n or a partial condensate thereof (i.e. polysiloxane), where R is a monovalent hydrocarbon radical, a hydrogen atom or an alkoxy group, at least one R being a hydrocarbon radical, n is from 1 to 3, R11 is hydrogen or a methyl group, R1 is a hydrocarbon radical containing less than 11 carbon atoms, a hydrogen atom or a hydroxyalkyl radical containing 2 or 3 carbon atoms, and Y is a chlorine atom or an acyloxy radical containing less than 4 carbon atoms. The compounds are preferably applied as an aqueous solution, which may be stabilized by acetic acid, the concentration for glass being from 0.1 to 1 per cent, but they may be applied undiluted or in organic solvents. After treatment, the glass is air-dried or heated at say 150 DEG C. Other surfaces mentioned include wood, metal and organic plastics. In an example, pieces of flat glass are dipped into 0.2 per cent aqueous solutions of the compound C17H38Si(OCH2CH2NMe2.HCl)3. One piece is not heated but is water-repellent; the other is heated at 150 DEG C. and is resistant to scratching. Specifications 654,540, [Group IV (b)], and 686,068 are referred to.ALSO:The invention comprises salts of aminoalkoxy silanes of the formula RnSi(OCHR11CH2NR12.HY)4-n, and partial condensates thereof, where R is a monovalent hydrocarbon radical, a hydrogen atom or an alkoxy radical, at least one R being a hydrocarbon radical, n is from 1 to 3, R11 is hydrogen or a methyl group, R1 is a hydrocarbon radical containing less than 11 carbon atoms, a hydrogen atom or a hydroxy-alkyl radical containing 2 or 3 carbon atoms, and Y is a chlorine atom or an acyloxy radical containing less than 4 carbon atoms. The silanes are best prepared by reacting silanes of the formula RnSiY4-n with amines of the formula R12NCH2CHR11OH. Solvents such as benzene, toluene, petroleum ether, methylene chloride and tertiary butanol may be present. The partial condensates may be prepared by partial hydrolysis of the aminosilanes or by reacting the amino-alcohols with halo- or acyloxy-siloxanes, e.g. of the formula RCl2SiOSiCl2R or RSi(OAc)0.5O. As hydrocarbon radicals, R and R1 may be alkyl, aryl, aralkyl, alkenyl or cycloaliphatic. The compounds are useful for treating glass surfaces, textiles, e.g. of cotton, wool, nylon, rayon and acrylonitrile fibres, paper, wood, metal, masonry and organic plastics. Aqueous solutions may be stabilized by adding a small amount of acetic acid to a pH of about 6. The examples describe the preparation of: (1) C18H37Si(OCH2CH2NMe2.HCl)3 (2) C3H7Si(OCH2CH2NMe2.HCl)3; (3) MeSi(OCH2CH2NMe2.HCl)3; (4) MeSi(OCH2CH2NH2.HCl)3; (5) Me3SiOCH2CH2NMe2.HCl; (6) C6H5Si(OCH2CH2NMe2.HCl)3; (7) Et2Si(OCH2CH2NMe2.HCl)2; (8) C18H37Si(OCH2CH2NEt2.HCl)3 (9) C18H37(OCH2CH2NHEt.HCl)3; (10) MeSi(OCH2CH2NH.C6H5.HCl)3; (11) MeSi(OCH2CH2NEt.Ph.HCl)3; <FORM:0786452/IV (a)/1> (13) CH2=CH.Si(OCH2CH2NMe2.CHl)3; (14) CH2=CH.Si(OCH2CH2NMe2.HOAc)3; <FORM:0786452/IV (a)/2> where x, y and z are not determined; (16) MeSi(OEt)2.(OCH2CH2NMe2.HCl); <FORM:0786452/IV (a)/3> (18) C18H37.Me2SiOCH2CH2NMe2.HCl; (19) MeHSi(OCH2CH2NMe2.HCl)2; <FORM:0786452/IV (a)/4> <FORM:0786452/IV (a)/5> <FORM:0786452/IV (a)/6> (24) A mixture of [HCl.Me2NCH2CH2O)2.-MeSi]2O, a trisiloxane, higher insoluble polysiloxanes, containing some original silane. Specifications 654,450, [Group IV (b)], and 686,068 are referred to.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US786452XA | 1954-09-10 | 1954-09-10 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB786452A true GB786452A (en) | 1957-11-20 |
Family
ID=22145373
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB25645/55A Expired GB786452A (en) | 1954-09-10 | 1955-09-07 | Improvements in or relating to organosilicon compounds |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB786452A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018848A1 (en) * | 1990-06-07 | 1991-12-12 | Daussan Et Compagnie | Method for producing a noise and/or heat protection covering, and covering thereby obtained |
| EP1088939A1 (en) * | 1999-09-29 | 2001-04-04 | Dow Corning Toray Silicone Co., Ltd. | Printing paper sizing agent composition |
| DE102005052762A1 (en) * | 2005-11-04 | 2007-05-10 | Wacker Chemie Ag | Novel alkanolamine-functional polyorganosiloxanes useful in corrosion protection of concrete-reinforcing steel and other uses have the silicon in a repeating unit bonded to three oxygens |
| JP2017014140A (en) * | 2015-06-30 | 2017-01-19 | 信越化学工業株式会社 | Aminoalkylalkoxydisiloxane compound and method for producing the same |
-
1955
- 1955-09-07 GB GB25645/55A patent/GB786452A/en not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO1991018848A1 (en) * | 1990-06-07 | 1991-12-12 | Daussan Et Compagnie | Method for producing a noise and/or heat protection covering, and covering thereby obtained |
| EP1088939A1 (en) * | 1999-09-29 | 2001-04-04 | Dow Corning Toray Silicone Co., Ltd. | Printing paper sizing agent composition |
| DE102005052762A1 (en) * | 2005-11-04 | 2007-05-10 | Wacker Chemie Ag | Novel alkanolamine-functional polyorganosiloxanes useful in corrosion protection of concrete-reinforcing steel and other uses have the silicon in a repeating unit bonded to three oxygens |
| DE102005052762B4 (en) * | 2005-11-04 | 2008-04-24 | Wacker Chemie Ag | Alkanolamine-functional polyorganosiloxanes |
| JP2017014140A (en) * | 2015-06-30 | 2017-01-19 | 信越化学工業株式会社 | Aminoalkylalkoxydisiloxane compound and method for producing the same |
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