GB858445A - Improvements in or relating to silanes - Google Patents
Improvements in or relating to silanesInfo
- Publication number
- GB858445A GB858445A GB40195/58A GB4019558A GB858445A GB 858445 A GB858445 A GB 858445A GB 40195/58 A GB40195/58 A GB 40195/58A GB 4019558 A GB4019558 A GB 4019558A GB 858445 A GB858445 A GB 858445A
- Authority
- GB
- United Kingdom
- Prior art keywords
- carbon
- meo
- nitrogen
- amine groups
- carbon atoms
- 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
- 150000004756 silanes Chemical class 0.000 title abstract 2
- 229910052799 carbon Inorganic materials 0.000 abstract 6
- 125000004432 carbon atom Chemical group C* 0.000 abstract 6
- 239000011521 glass Substances 0.000 abstract 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 5
- 239000007864 aqueous solution Substances 0.000 abstract 5
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 5
- 125000004433 nitrogen atom Chemical group N* 0.000 abstract 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 abstract 4
- -1 aliphatic hydrocarbon radical Chemical group 0.000 abstract 4
- 150000003254 radicals Chemical class 0.000 abstract 4
- CNPURSDMOWDNOQ-UHFFFAOYSA-N 4-methoxy-7h-pyrrolo[2,3-d]pyrimidin-2-amine Chemical group COC1=NC(N)=NC2=C1C=CN2 CNPURSDMOWDNOQ-UHFFFAOYSA-N 0.000 abstract 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 abstract 3
- 125000000217 alkyl group Chemical group 0.000 abstract 3
- 125000003277 amino group Chemical group 0.000 abstract 3
- 150000001875 compounds Chemical class 0.000 abstract 3
- 239000004744 fabric Substances 0.000 abstract 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 abstract 2
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 abstract 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 abstract 2
- 229910052739 hydrogen Inorganic materials 0.000 abstract 2
- 239000001257 hydrogen Substances 0.000 abstract 2
- 229910052757 nitrogen Inorganic materials 0.000 abstract 2
- 239000003960 organic solvent Substances 0.000 abstract 2
- 150000003961 organosilicon compounds Chemical class 0.000 abstract 2
- 229920000768 polyamine Polymers 0.000 abstract 2
- 229910000077 silane Inorganic materials 0.000 abstract 2
- PEAGNRWWSMMRPZ-UHFFFAOYSA-L woodstain scarlet Chemical compound [Na+].[Na+].OC1=CC=C2C=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1N=NC(C=C1)=CC=C1N=NC1=CC=CC=C1 PEAGNRWWSMMRPZ-UHFFFAOYSA-L 0.000 abstract 2
- XXJGBENTLXFVFI-UHFFFAOYSA-N 1-amino-methylene Chemical compound N[CH2] XXJGBENTLXFVFI-UHFFFAOYSA-N 0.000 abstract 1
- RXVPXYLWGITCJV-UHFFFAOYSA-N 3-(2-aminoethyl)hexane-1,6-diamine Chemical compound NCCCC(CCN)CCN RXVPXYLWGITCJV-UHFFFAOYSA-N 0.000 abstract 1
- MCGBIXXDQFWVDW-UHFFFAOYSA-N 4,5-dihydro-1h-pyrazole Chemical compound C1CC=NN1 MCGBIXXDQFWVDW-UHFFFAOYSA-N 0.000 abstract 1
- VVYWUQOTMZEJRJ-UHFFFAOYSA-N 4-n-methylbenzene-1,4-diamine Chemical compound CNC1=CC=C(N)C=C1 VVYWUQOTMZEJRJ-UHFFFAOYSA-N 0.000 abstract 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 abstract 1
- 239000000980 acid dye Substances 0.000 abstract 1
- HAMNKKUPIHEESI-UHFFFAOYSA-N aminoguanidine Chemical compound NNC(N)=N HAMNKKUPIHEESI-UHFFFAOYSA-N 0.000 abstract 1
- RUOKPLVTMFHRJE-UHFFFAOYSA-N benzene-1,2,3-triamine Chemical compound NC1=CC=CC(N)=C1N RUOKPLVTMFHRJE-UHFFFAOYSA-N 0.000 abstract 1
- NHOWLEZFTHYCTP-UHFFFAOYSA-N benzylhydrazine Chemical compound NNCC1=CC=CC=C1 NHOWLEZFTHYCTP-UHFFFAOYSA-N 0.000 abstract 1
- 150000001721 carbon Chemical group 0.000 abstract 1
- 238000000576 coating method Methods 0.000 abstract 1
- 238000007598 dipping method Methods 0.000 abstract 1
- 238000001035 drying Methods 0.000 abstract 1
- 125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 abstract 1
- NHWGPUVJQFTOQX-UHFFFAOYSA-N ethyl-[2-[2-[ethyl(dimethyl)azaniumyl]ethyl-methylamino]ethyl]-dimethylazanium Chemical compound CC[N+](C)(C)CCN(C)CC[N+](C)(C)CC NHWGPUVJQFTOQX-UHFFFAOYSA-N 0.000 abstract 1
- 229910052736 halogen Inorganic materials 0.000 abstract 1
- 150000002367 halogens Chemical class 0.000 abstract 1
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 abstract 1
- 230000007062 hydrolysis Effects 0.000 abstract 1
- 238000006460 hydrolysis reaction Methods 0.000 abstract 1
- 150000002466 imines Chemical class 0.000 abstract 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- HDZGCSFEDULWCS-UHFFFAOYSA-N monomethylhydrazine Chemical compound CNN HDZGCSFEDULWCS-UHFFFAOYSA-N 0.000 abstract 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 abstract 1
- 238000002360 preparation method Methods 0.000 abstract 1
- 229920005989 resin Polymers 0.000 abstract 1
- 239000011347 resin Substances 0.000 abstract 1
- 229910052710 silicon Inorganic materials 0.000 abstract 1
- 150000003377 silicon compounds Chemical class 0.000 abstract 1
- 239000000243 solution Substances 0.000 abstract 1
- 238000005507 spraying Methods 0.000 abstract 1
- 235000011149 sulphuric acid Nutrition 0.000 abstract 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 210000002268 wool Anatomy 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
- C07F7/18—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)
- Paints Or Removers (AREA)
- Silicon Polymers (AREA)
Abstract
The invention comprises aminohydrocarbon trialkoxy silanes of the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n + 1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond and is composed of carbon, hydrogen and nitrogen atoms, all the nitrogen being present as amine groups, the ratio of carbon to nitrogen atoms in R1Zn being less than 6:1. The radical R1 includes any number and combination of <FORM:0858445/IV(a)/1> vinylene and methylene groups which may contain methyl and vinyl groups. The amine groups may be primary, secondary or tertiary and include imines. The compounds may be prepared by reacting a polyamine with a halohydrocarbonyl trialkoxy silane where the halogen is on a carbon atom which is alpha or at least gamma to the silicon atom, preferably at temperatures of 50 DEG to 200 DEG C. under anhydrous conditions. Suitable polyamines are ethylene diamine, diethylene triamine, 1, 6-hexanediamine, 3-aminoethyl-1, 6-diamino-hexane, N, N1-dimethyl hexamethylene diamine, cadaverine, piperazine, di-1, 2-propane diamine, methyl hydrazine, 1-aminoguanidine, 2-pyrazoline, benzene triamine, benzene pentamine, benzyl hydrazine, N-methyl-p-phenylene diamine, N, Ndimethyl-p-phenylene diamine and 3-o-tolylene diamine. The products are water-soluble and aqueous solutions are used to provide coatings of siloxanes on glass. The examples describe the preparation of: (1) and (2) (RO) 3SiCH2CH2CH2 NHCH2CH2NH2, where R is Me, Et, n-Pr and i-Pr; (3)(MeO) 3SiCH2CHMECH2NHCH2CH2 NH2, (MeO) 3SiCH = CH CH2NHCH2CH2 NH2, (MeO) 3SiCH2CH = CHCH2CH2NHCH2 CH2NH2, (MeO) <FORM:0858445/IV(a)/2> and (4) and (5) a number of other compounds such as <FORM:0858445/IV(a)/3> and (MeO) 3SiCH2NHC6H4NMe2. Specification 804,097 is referred to.ALSO:Glass cloth is coated with an organosilicon compound and dyed with any direct acid dye such as is employed on wool, the silicon compound having the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n+ 1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond, the ratio of carbon to nitrogen atoms in R1Zn being less than 6 : 1 (see Group IV(a)). In examples (6) heat-cleaned glass cloth is immersed in a 0,5% aqueous solution of (MeO)3Si CH2 CH2 CH2 NH CH2 CH2 NH2, air-dried, and dyed (a) by immersing in a 3% aqueous solution of Brilliant Croceine 3BA containing 4% H2SO4 at a temperature of 95 DEG C. for 1 hour, (b) with Nigrosine ESB Cl 865, and (c) with Pontachrome Brown RH; (7) heat-cleaned glass cloth is immersed in a 1% aqueous solution of (MeO)3 Si CH2 CH2 CH2 NH CH2 CH2 NH2, heated at 110 DEG C. for 10 mins. and dyed with aqueous Brilliant Croceine 3BA.ALSO:Glass is coated with an organosilicon compound of the formula (RO)3SiR1Zn, where R is an alkyl group of 1 to 3 carbon atoms, R1 is an aliphatic hydrocarbon radical of one or more than two carbon atoms and a valency of n+1, n is at least 1, and Z is a monovalent radical containing at least 2 amine groups attached to R1 through a carbon-nitrogen bond and is composed of carbon, hydrogen and nitrogen atoms, all the nitrogen being present as amine groups, the ratio of carbon to nitrogen atoms in R1Zn being less than 6:1 (see Group IV(a)). p The compounds may be applied as solutions in water or organic solvents, by any common method, e.g. dipping or spraying, preferably as 0.1 to 3% aqueous solutions followed by drying advantageously at a raised temperature. The result is a glass base coated with a hydrolysis product of the silane, providing improved adhesion of organic resins and wettability by organic solvents, and which may be dyed.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US858445XA | 1957-12-23 | 1957-12-23 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB858445A true GB858445A (en) | 1961-01-11 |
Family
ID=22194323
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB40195/58A Expired GB858445A (en) | 1957-12-23 | 1958-12-12 | Improvements in or relating to silanes |
Country Status (1)
Country | Link |
---|---|
GB (1) | GB858445A (en) |
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4416794A (en) | 1981-09-25 | 1983-11-22 | The Procter & Gamble Company | Rinse aid compositions containing amino-silanes |
US4416793A (en) | 1981-09-25 | 1983-11-22 | The Procter & Gamble Company | Liquid detergent compositions containing amino-silanes |
US4446033A (en) * | 1981-09-25 | 1984-05-01 | The Procter & Gamble Company | Fabric conditioning compositions containing amino-silanes |
US4446035A (en) * | 1981-09-25 | 1984-05-01 | The Procter & Gamble Company | Cleansing agents and the like with amino-silanes |
US4448699A (en) * | 1981-09-25 | 1984-05-15 | The Procter & Gamble Company | Laundry additive products containing amino-silanes |
-
1958
- 1958-12-12 GB GB40195/58A patent/GB858445A/en not_active Expired
Cited By (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4416794A (en) | 1981-09-25 | 1983-11-22 | The Procter & Gamble Company | Rinse aid compositions containing amino-silanes |
US4416793A (en) | 1981-09-25 | 1983-11-22 | The Procter & Gamble Company | Liquid detergent compositions containing amino-silanes |
US4446033A (en) * | 1981-09-25 | 1984-05-01 | The Procter & Gamble Company | Fabric conditioning compositions containing amino-silanes |
US4446035A (en) * | 1981-09-25 | 1984-05-01 | The Procter & Gamble Company | Cleansing agents and the like with amino-silanes |
US4448699A (en) * | 1981-09-25 | 1984-05-15 | The Procter & Gamble Company | Laundry additive products containing amino-silanes |
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