WO2007031775A1 - Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon-compounds - Google Patents
Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon-compounds Download PDFInfo
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- WO2007031775A1 WO2007031775A1 PCT/GB2006/003440 GB2006003440W WO2007031775A1 WO 2007031775 A1 WO2007031775 A1 WO 2007031775A1 GB 2006003440 W GB2006003440 W GB 2006003440W WO 2007031775 A1 WO2007031775 A1 WO 2007031775A1
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- YCIMNLLNPGFGHC-UHFFFAOYSA-N Oc1ccccc1O Chemical compound Oc1ccccc1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a method for inducing a hypervalent state within silicon-containing compounds by which they can be chemically attached to a surface or substrate and/or organized onto a surface of a substrate.
- the compounds when attached to or organised on the surface may have different physical and/or chemical properties compared to the starting materials.
- the present invention provides a method for the chemical attachment of one or more silicon- containing compounds to a substrate, ' the method comprising: providing one or more silicon-containing compounds selected from siloxane compounds, silanol compounds, silyl ether compounds, silanolate compounds, halosilane compounds, silatrane compounds, and silazane compounds; contacting one or more of the silicon-containing compounds with a surface of a substrate having one or more nucleophilic sites thereon; and exposing the silicon-containing compounds and the surface to electromagnetic radiation having a frequency from 0.3 to 30 GHz.
- the present invention provides a method for creating an array of silicon-containing compounds on a surface of a substrate, the method comprising : providing one or more silicon-containing compounds selected from siloxane compounds, silanol compounds, silyl ether compounds, silanolate compounds, halosilane compounds, silatrane compounds, and silazane compounds; contacting one or more of these silicon-containing compounds with a surface of a substrate; and exposing the substrate and the silicon-containing compounds to electromagnetic radiation having a frequency of from 0.3 to 30 GHz.
- the substrate may have one or more nucleophilic sites on its surface or one or more compounds having nucleophilic groups, such as alcohols, may be present on the surface.
- the surface of the substrate may be on the exterior or interior of the substrate.
- the substrate may, for example, be a porous polymer matrix and the silicon-containing compounds may be arranged on or attached to the interior surfaces of the pores of the matrix.
- the present invention provides a method for the synthesis of silicon-containing hypervalent compounds, the method comprising: providing one or more silicon-containing compounds selected from siloxane compounds, silanol compounds, silyl ether compounds, silanolate compounds, halosilane compounds, silatrane compounds, and silazane compounds; optionally contacting the one or more silicon- containing compounds with a surface of a substrate; and exposing the silicon-containing compounds and, if present, the substrate to electromagnetic radiation having a frequency of from 0.3 to 30 GHz.
- the substrate may have one or more nucleophilic sites on its surface or one or more compounds having nucleophilic groups, such as alcohols, may be present, and if a substrate is present, they may be located on the surface of the surface.
- the present invention provides a substrate having one or more silicon-containing compounds on the surface thereof, wherein the one or more silicon- containing compounds have been attached to the surface by the method of the present invention.
- the present invention provides a substrate having one or more silicon-containing compounds on the surface thereof, wherein the one or more silicon- containing compounds have been organized into an array on the surface by the method of the present invention.
- the present invention provides a hypervalent silicon-containing compound formable by the method of the present invention.
- the silicon-containing compound may be a compound of the formula I
- Ri is hydrogen or an alkyl, preferably a Ci to C 6 alkyl, more preferably, a Ci or a C 2 alkyl, such as methyl or ethyl, and m is 1 to 4, preferably 3;
- the polymer preferably includes electron donor groups on at least some, of its monomers . These electron donor groups may be substituents on R 2 and/or R 3 in the formula II above. Electron donor groups include, but are not limited to, hydroxyl , amine, sulfhydryl and carboxyl .
- Electron donor groups include, but are not limited to, hydroxyl , amine, sulfhydryl and carboxyl .
- X the number of repeating units in the polymer, may be any appropriate number. X may be 2 to 10,000, preferably 2 to 1000. •
- Alkyl is preferably a Ci to C 2 s alkyl, and may be C 3 to C 18 alkyl. Alkyl may be a substituted or non-substituted alkyl. Alkyl may be a halo-alkyl, preferably a haloalkyl in which a halo group is located at the distal end of the alkyl chain from the silicon. The haloalkyl is preferably a chloroalkyl .
- the silicon-containing compound is a compound of formula I, wherein m is 3, n is 1 and o and p are both 0, R 1 is hydrogen, methyl or ethyl.
- At least one of R 2 , R 3 and/or R 4 is of the formula III
- R 5 is selected from hydrogen, halogen, NH 2 , C 1 to C 18 alkyl, C 1 to C 18 alkyldimethylammonium, alkylmethacryate , preferably ethyl or propylmethacrylate, 5, 5-dialkylhydantoin, preferably 5, 5-dimethylhydantoin, alkylenediamine, preferably ethylenediamine, perfluoroalkyl, preferably perfluorooctyl and 3-glycidoxy.
- the silicon-containing compound may comprise one or more of [3- (trimethoxysilyl) propyl] - octadecyldimethylammonium chloride, 3(3- triethoxysilylpropyl) -5, 5-dimethylhydantoin, potassium trimethylsilanolate, triisopropylsilanol , methoxydimethyloctylsilane, hydroxy terminated poly (dimethylsiloxane) , (3-chloropropyl) triethoxysilane, (3-chloropropyl) dimethoxymethylsilane, octadecyltrimethoxysilane, 3-aminopropyltriethoxysilane, 3- (trimethoxysilyl)propylmethacrylate, N- [3- (trimethoxysilyl) propyl] -ethylenediamine, and 3- glycidoxypropyltrimethoxys
- the silicon-containing compound is [3- (trimethoxysilyl) propyl] -octadecyldimethylammonium chloride or 3 (3 -triethoxysilylpropyl) -5, 5-dimethylhydantoin,
- a solution of suspension of the silicon containing compounds may be contacted with the substrate.
- the solution and/or suspension preferably comprises a polar solvent, more preferably acetone and/or an alcohol, preferably both.
- the alcohol preferably comprises methanol and/or ethanol .
- the silicon-containing compound may be solvent-free, i.e. not in the form of a solution or suspension.
- the substrate is preferably a material having nucleophilic sites on its surface.
- the nucleophilic sites may comprise one or more nucleophilic groups containing one or more of 0, S and N.
- the nucleophilic groups may be selected from OH, SH and NH 2 .
- the substrate may comprise a fabric material .
- nucleophilic groups bind to the silicon atoms of the silicon-containing compounds on contact and with exposure to electromagnetic radiation having a frequency of from-0.3 to 30 GHz. This reaction normally occurs within seconds, as opposed to hours for conventional methods, such as merely heating.
- the method of the present invention can produce organised alignment (i.e. an array) of silicon-containing compounds on the surface of a substrate.
- the properties of the silicon-containing compounds often differ from those of the prior art, e.g. silicon compounds attached through the use of heat.
- the silicon-containing compounds on the substrate may have different physical and chemical properties such as increased hydrophobicity or hydrophilicity and/or increased biocidal efficacy.
- the hypervalent state is believed to leads to a more organised arrangement of silicon-containing compounds on the surface of a substrate.
- Hypervalency in silicon has been shown to occur in the following known reaction between tetramethoxy silane and catechol , which was carried out in ethanol under microwave treatment :
- the hypervalent-silicon products produced in the above reactions are sufficiently stable to be characterised. It is believed that a similar hypervalency occurs in the process of the present invention, although the hypervalent silicon may revert to a tetravalent silicon following microwave treatment. It is surprising that, irrespective of whether or not the silicon remains in a hypervalent state following the microwave treatment, a more organised arrangement of silicon-containing compounds on the surface of the substrate is observed.
- Si-OR excitation via electromagnetic radiation in the presence of an appropriate electron donor facilitates the cleavage of the Si-OR bond and is believed to induce the formation of hypervalent siloxane species with available electron donors.
- the electron donor for this exchange can take the form of virtually any nucleophile, induced nucleophile, nucleophilic region, or Lewis base.
- the resulting hypervalent species is then thought to either relax into their ground state, at which time the silane species is tetracoordinate, or, if the hypercoordinated product is stable, the silane product can remain in the hypervalent state as either a pentacoordinate or hexacoordinate system.
- the electromagnetic excitation within the siloxane induces specific conformations within the new species, which leads to increased and specific organization in the resting state of the newly formed species.
- the substrate is a polymer
- the specific organization of the silicon-containing on the surface or in the matrix of a polymer can change the chemical and physical properties of the polymer as a whole. This phenomenon is not temperature dependant .
- the method of the present invention avoids the need to use activators, catalysts and conventional curing processes. This therefore allows the attachment of 'delicate' functionalities.
- glycidoxy containing siloxane and acrylate containing siloxanes are examples of delicate silicon containing compounds and proteins/enzymes are .
- delicate substrates to which one may wish to attach a silicon-containing substrate.
- the microwaves are produced using a power rating of 650 Watts or less, more preferably of from 65 to 650 Watts.
- the microwaves may be produced using a power rating of from 135 to 400 Watts.
- the microwaves have a frequency of from 0.3 to 10 GHz, more preferably of from 1 to 3 GHz.
- irradiation at a reduced power level for example microwaves produced using a power rating of 400 Watts or less, preferably 135 Watts or less, or subjecting the substrate and silicon-containing compounds to microwave irradiation and relaxation (no microwave irradiation) in alternating intervals: for example a period of irradiation of preferably 5 to 30 seconds, more preferably 10 to 20 seconds, most preferably 15 seconds, followed by a period of relaxation of preferably 2 to 30 seconds, more preferably 5 to 15 seconds, most preferably 10 seconds, and optionally repeating this process as often as required.
- the microwaves can be directed at particular portions of the substrate and therefore allows for regioselective attachment and/or arrangement of the silicon-substituted compounds and for reactions that can be initiated that would not be possible using traditional methods.
- the present invention has been found to be far more effective in attaching silicon-containing compounds to a substrate surface compared to traditional methods such as heating and using activators - more than 80% of the silicon- containing compounds can be attached under certain conditions to the surface using the method of the present invention.
- the substrate may comprise a natural material.
- the material may be a cloth material .
- the material may comprise one or more materials selected from cotton, wool and leather.
- the material may be woven or non-woven.
- the material may comprises fibres of natural and/or synthetic material .
- the synthetic material may comprise a woven or nonwoven fabric material to include, but not limited to fabrics wherein the material comprises one or more of the following; cotton, polyester, nylon, wool, leather, rayon, polyethylene, polyvinylchloride, polyvinylalcohol, polyvinylamine and polyurea.
- the substrate may be in the form of particles.
- the particles may have a diameter of from 10 nm to 1 mm, preferably 100 to 1000 nm.
- the substrate may comprise a metal oxide.
- the metal oxide may be selected from one or more of aluminium oxide, titanium dioxide, magnesium oxide, calcium oxide, silicon dioxide and zinc oxide.
- the substrate may comprise a natural mineral .
- the substrate may comprise one or more materials selected from kaolinite, barasym, silica, montmorillonite, vermiculite, bohemite and quartz.
- the substrate may be porous.
- the substrate may comprise a molecular sieve.
- the substrate may comprise a zeolite .
- the substrate may comprise a polymer.
- the polymer may be in the form of a porous matrix.
- the substrate may comprise a plastic material.
- the substrate may comprise polyurethane and/or nylon, polyester, nylon, rayon, polyethylene, polyvinylchloride, polyvinylalcohol, polyvinylamine and polyurea.
- the substrate may comprise a carbohydrate.
- an alcohol may be present.
- the substrate may comprise an alcohol.
- the substrate may have an alcohol on its surface.
- the alcohol may comprise a diol , which may be a vicinal diol, or a triol .
- the alcohol may be selected from one or more of an alkyl diol , preferably a C 2 to C 2 ⁇ alkyl diol , an alkyl triol, preferably a C 3 to C 25 alkyl triol and a phenyl diol, preferably a vicinal phenyl diol.
- Each hydroxyl group in the triol is preferably vicinal to one of the other hydroxyl groups.
- the alcohol may be selected from catechol, ethylene glycol or glycerol .
- the substrate may comprise a silicon-dioxide based material, such as glass, silicon dioxide, sand, and silica.
- the method of the present invention may involve: contacting the substrate with, a silicon-containing compound as defined herein and exposing the compounds to electromagnetic radiation having a frequency of from 0.3 to 30 GHz, and subsequently treating the substrate with a halogenating substance.
- the silicon-containing compound preferably comprises 3 (3-triethoxysilylpropyl) -5, 5- dimethylhydantoin.
- the halogenating substance may comprise a chlorinating substance, including, but not limited to a bleaching agent, for example a hypochlorite such as sodium hypochlorite .
- the substrate may be dried.
- the substrate may be dried by exposing the substrate to a temperature of 20 °C or more, preferably 30°C or more, more preferably 35 0 C for a period including, but not limited to, 1 hour or more, preferably 4 hours or more.
- Each solution contained acetone, ethanol and methanol.
- Each swatch of cotton was then irradiated at a frequency between 0.30-30 GHz for a period of time dependant on the properties of the silicon containing compound that was attached. All experiments were performed initially at 2.45 Ghz, with power level being varied depending on the nature of the attached functional group. In general, the procedure was first attempted at full power for full two cycles of the following program: 30s 50% power (325 Watts) , 30s relaxation (magnetron disengaged) , 30s 50% power, 30s relaxation, 30s 100% power, allow to cool to room temperature, then repeat cycle. If the procedure "cracked" the reactants, then the irradiation time and power level were reduced accordingly until the procedure yielded the desired result. The samples were then washed, rinsed thoroughly and dried overnight at 35° C.
- the attachment of the silicon-containing compounds was confirmed by: 1. an overall increase in weight of the cloth (all samples), 2. a change in the physical characteristics of the cloth (all), 3.biocidal efficacy of the treated fabric (2 samples, see below), 4. FTIR spectroscopy (all), 5. elemental analysis (all), and 6. ionic strength of the product in distilled, deionized water (all) .
- Example 1 the method is nonspecific with respect to the type of functionality that can be attached, and the compound may comprise a silyl ether, silanol, or silanolate; 2. The process works for silyl ethers, silanols and silanolates; and 3. by tuning the frequency and power level, the method can be tailored to avoid degradation of with other functionalities within the system; and 4. the process works on cotton.
- Each solution contained one or more of acetone, ethanol and methanol .
- bohemite 100 mg is approximately 1 mmol .
- bohemite approximately 0.1 mmol of silane dissolved in approximately 0.5-1.0 mL of acetone was added.
- the MW of 3 (3-triethoxysilylpropyl) -5 , 5- dimethylhydantoin is 332, so 33.2 mg of silane was dissolved in 1 mL.
- the procedure was scaled up to full molar scale. Surprisingly, the "batch" scale actually worked much better than this small scale experiment, i.e.. a higher and better degree of attachment of the silicon on the bohemite was observed.
- Example 2 The irradiation procedure described in Example 1 above was used. The samples were then washed with a minimal amount of ice cold ethanol and then twice with surfactant-containing water; the samples were then rinsed with water thoroughly and dried overnight at 35° C.
- the attachment of the silicon-containing compounds was confirmed by: 1. a change in the physical characteristics of the treated nanoparticles, 2. biocidal efficacy of the treated nanoparticles (2 samples, in particular: solutions 1 and 2), 4. FTIR spectroscopy (all), 5. elemental analysis (all), and 6. ionic strength of the product in distilled, deionized water (all) .
- Example 2 Conclusions from Example 2 : 1. the process is nonspecific with respect to the type of functionality that can be attached, and the silicon-containing compounds can include a silyl ether, silanol, or silanolate; 2. by tuning the frequency and power level, the process can be tailored not to interfere with other functionalities within the system; and 3. The process works well on bohemite
- the substrate samples were: 1. Cotton, 2. aluminum oxide, 3. titanium dioxide, 4. glass, 5. nylon, 6. kaolinite, 7. barasym, 8. silicon dioxide, 9. wool, 10. leather, 11. silica, 12. molecular sieves, 13. montmorillonite, 15. polyurethane , 16. ethylene glycol, 17. glycerol, 18. catechol, 19. zeolite, 20. vermiculite, 21. bohemite,. 22. polyester. 23. triethanolamine
- the samples were irradiated at a frequency between 0.30-30 GHz for a period of time, all dependant on the microwave absorbing properties of the substrate.
- the irradiation procedure described in Example 1 above was used.
- the samples were then washed, rinsed thoroughly and dried overnight at 35° C.
- the samples treated with 3(3- triethoxysilylpropyl) -5 , 5-dimethylhydantoin) were also charged with dilute hypochlorite (to generate the chloramine) and again washed, rinsed and dried.
- Example 3 the process will work for any substrate that contains an appropriate S, and/or 0, and/or N, and/or Nu; 2. by tuning the frequency and power level, the process can be tailored not to interfere with other functionalities within the system; and 3. the irradiated materials are distinctly different from the equivalent heat treated version (from HNMR and GCMS)
- Example 4 the irradiation process is more effective and efficient than heat treatment at attaching silyl ethers, silanols and silanolates to substrates.
- Example 5 the irradiation process is more effective and efficient than heat treatment at attaching silyl ethers, silanols and silanolates to substrates.
- Example 5 The irradiated materials are distinctly different from the equivalent heat treated version. The irradiation process produces a product that is a more efficient sporicide than the heat cured process.
Abstract
Description
Claims
Priority Applications (7)
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CA2622087A CA2622087C (en) | 2005-09-15 | 2006-09-15 | Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon-compounds |
BRPI0615847-1A BRPI0615847A2 (en) | 2005-09-15 | 2006-09-15 | methods for chemically bonding one or more silicon-containing compounds to a substrate and for arranging an arrangement of silicon-containing compounds on a substrate surface, substrate, method for synthesizing silicon-containing hypervalent compounds; |
AU2006290509A AU2006290509B2 (en) | 2005-09-15 | 2006-09-15 | Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon-compounds |
CN2006800335954A CN101263257B (en) | 2005-09-15 | 2006-09-15 | Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon compounds |
EP06779452.9A EP1924734B1 (en) | 2005-09-15 | 2006-09-15 | Method for attachment of silicon-containing compounds to a surface and for the synthesis of hypervalent silicon-compounds |
JP2008530621A JP2009509053A (en) | 2005-09-15 | 2006-09-15 | Method for attaching a silicon-containing compound to a silicon compound surface in a hypervalent state and a method for producing a silicon compound in a hypervalent state |
IL189783A IL189783A0 (en) | 2005-09-15 | 2008-02-26 | Methods for attachment of silicon-containing compounds to a surface |
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GB0608534A GB2431173B (en) | 2005-09-15 | 2006-04-28 | Method for attachment of silicon-containing compounds to a surface |
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US (2) | US20100239784A1 (en) |
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CN (1) | CN101263257B (en) |
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CA (1) | CA2622087C (en) |
GB (1) | GB2431173B (en) |
HK (1) | HK1102231A1 (en) |
IL (1) | IL189783A0 (en) |
RU (1) | RU2008114505A (en) |
TW (1) | TW200720324A (en) |
WO (1) | WO2007031775A1 (en) |
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RU2008114505A (en) | 2009-10-20 |
CN101263257B (en) | 2013-03-27 |
CN101263257A (en) | 2008-09-10 |
EP1924734B1 (en) | 2017-01-04 |
AU2006290509A2 (en) | 2008-05-15 |
IL189783A0 (en) | 2008-08-07 |
GB0608534D0 (en) | 2006-06-07 |
EP1924734A1 (en) | 2008-05-28 |
US20100239784A1 (en) | 2010-09-23 |
CA2622087A1 (en) | 2007-03-22 |
GB2431173B (en) | 2010-01-13 |
HK1102231A1 (en) | 2007-11-09 |
BRPI0615847A2 (en) | 2011-05-31 |
GB2431173A (en) | 2007-04-18 |
KR20080059211A (en) | 2008-06-26 |
US20120128930A1 (en) | 2012-05-24 |
CA2622087C (en) | 2014-10-28 |
TW200720324A (en) | 2007-06-01 |
AU2006290509B2 (en) | 2012-01-12 |
AU2006290509A1 (en) | 2007-03-22 |
JP2009509053A (en) | 2009-03-05 |
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