US20010018130A1 - Capped silicone film and method of manufacture thereof - Google Patents

Capped silicone film and method of manufacture thereof Download PDF

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US20010018130A1
US20010018130A1 US09/803,280 US80328001A US2001018130A1 US 20010018130 A1 US20010018130 A1 US 20010018130A1 US 80328001 A US80328001 A US 80328001A US 2001018130 A1 US2001018130 A1 US 2001018130A1
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Don Hayden
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    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00Processes for applying liquids or other fluent materials
    • B05D1/36Successively applying liquids or other fluent materials, e.g. without intermediate treatment
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y30/00Nanotechnology for materials or surface science, e.g. nanocomposites
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00Processes for applying liquids or other fluent materials
    • B05D1/18Processes for applying liquids or other fluent materials performed by dipping
    • B05D1/185Processes for applying liquids or other fluent materials performed by dipping applying monomolecular layers
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B05SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05DPROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D3/00Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/10Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by other chemical means
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B82NANOTECHNOLOGY
    • B82YSPECIFIC USES OR APPLICATIONS OF NANOSTRUCTURES; MEASUREMENT OR ANALYSIS OF NANOSTRUCTURES; MANUFACTURE OR TREATMENT OF NANOSTRUCTURES
    • B82Y40/00Manufacture or treatment of nanostructures
    • CCHEMISTRY; METALLURGY
    • C03GLASS; MINERAL OR SLAG WOOL
    • C03CCHEMICAL 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
    • C03C17/00Surface treatment of glass, not in the form of fibres or filaments, by coating
    • C03C17/28Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
    • C03C17/30Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D4/00Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T428/00Stock material or miscellaneous articles
    • Y10T428/31504Composite [nonstructural laminate]
    • Y10T428/31652Of asbestos
    • Y10T428/31663As siloxane, silicone or silane

Definitions

  • This invention relates generally to silicone films, and more specifically to application of such films to glass and other surfaces.
  • the glass is coated with a film consisting of chains of silicone molecules, with each chain chemically bound at one end to the surface of the glass.
  • Each chain contains from dozens to hundreds of dimethylsiloxane (DMS) units and is terminated at its free end by either a hydroxyl (OH) group or a chlorine attached to a silicon, which soon reacts with water vapor in the air to produce OH groups.
  • DMS dimethylsiloxane
  • OH hydroxyl
  • This existing film is in use on a number of glass products as well as other silica-containing products such as granite, porcelain, earthenware and stoneware, and for the most part, has performed satisfactorily.
  • the water-repellence of the film is limited to some extent by the presence of the terminal OH groups, which are highly water-attracting.
  • Another object of the invention is to produce a family of silicone films for treating a variety of products such as the silica-containing products previously mentioned as well as organic substances including paper, cotton, nylon, leather, and wood, in order to improve the surface properties of those products.
  • a silicone film is attached to a surface by chemical bonding.
  • the silicone film consists of chains of siloxane groups, each chain terminating in an end molecule which is either an ester, an ether, or a halogen.
  • the end molecule is allowed to react with water, either water vapor in the surrounding air or by covering the surface with liquid water, to produce an end OH group.
  • the surface is then contacted with a capping agent which reacts with the OH group to produce a new end group which improves the properties of the film.
  • siloxane groups used, as well as the composition of the capping agent.
  • the siloxane groups have the formula
  • R consists of nonpolar groups
  • R 1 consists of inert groups.
  • R consists of polar or nonpolar groups.
  • R 1 could consist of chemically active groups, enabling the surface to be used as a solid state ion exchanger or an attachment point for chemically bound enzymes, chelating agents, dyes, chemical indicators or other substances.
  • FIG. 1 is a diagrammatic representation of a surface coated with a prior art water-repellent film
  • FIG. 2 is a diagrammatic representation of a surface coated with a water-repellent film manufactured using the process of the present invention.
  • FIG. 1 shows a surface G which has been treated with a water-repellent film using a prior art process.
  • the surface G is glass, but the process may actually be used to treat any surface containing OH or nitrogen hydrogen bonds, such as silica-containing surfaces including granite, porcelain, earthenware and stoneware, as well as organic substances including cotton, paper, nylon, leather and others.
  • the film comprises chains of dimethylsiloxane (DMS) groups. Each chain is chemically bonded at one end to an oxygen (O) molecule, which in turn is chemically bonded to the surface G.
  • the opposite end of each chain includes either a hydroxyl (OH) group or a chlorine attached to silicone, which will soon react with water vapor in the surrounding air to produce an OH group.
  • DMS dimethylsiloxane
  • the surface is treated with dimethyldichlorosilane using Portable Vapor machines which may be adapted to fixed site chambers for large volume operations, or by using a wipe-on method or a dipping or spraying procedure. Where necessary, cyclohexylamine is used as a primer to ensure sufficient moisture for the chemical reaction to take place.
  • a dimethyldichlorosilane molecule approaches an O—H group at the surface, as shown below:
  • n is around 100 or more.
  • the groups in the brackets are highly water repellent. However, the chlorine atom at the end of the chain slowly reacts over several hours with water vapor in the air to result in a product having the formula:
  • TMS trimethylchlorosiloxane
  • the silicone film produced by the process of steps (a)-(i) above is one specific example of the invention, intended for water-repellent applications.
  • the moistened surface G is first contacted with silane groups having the formula
  • R represents polar or nonpolar groups including hydrocarbons or halogenated hydrocarbons
  • X is selected from the group consisting of esters, ethers, and halogens.
  • the silane groups then react with the OH or nitrogen hydrogen bonds and water at the surface G to chemically bond the film to the surface G, in a process analogous to step (b) above.
  • a series of reactions analogous to those shown in steps (b)-(f) above results in a polymer having the formula:
  • n is around 100 or more.
  • the X atom at the end of the chain then reacts with water vapor in the surrounding air resulting in a molecule having the formula:
  • R 1 may include any combination of inert and reactive groups.
  • the capping agent reacts with the OH group at the end of the chain, resulting finally in a chain having the formula:
  • R consists of nonpolar groups and R 1 consists of chemically inert groups. If R consists of approximately 50% methyl groups and 50% phenyl groups, the abrasion-resistance of the film is improved.
  • the abrasion-resistance of the film can also be improved by connecting the DMS chains with methyltrichlorosilane (which causes branched chains and additional ends). The methyltrichlorosilane would cause the chains to be tied together in a three-dimensional structure, which would resist abrasion better than a two-dimensional structure.
  • R consists of polar or nonpolar groups. If R 1 is selected from chemically reactive groups, the end molecule can provide an attachment point for enzymes, chelating agents, ion exchange elements, chemical indicators and other substances.

Abstract

A silicone film is attached to a surface by chemical bonding. The silicone film consists of chains of siloxane groups, each chain terminating in an end molecule which is either an ester, an ether, or a halogen. The end molecule is allowed to react with water to produce an OH group. The surface is then contacted with a capping agent which reacts with the OH group to produce a new end group which improves the properties of the film.

Description

    BACKGROUND OF THE INVENTION
  • 1. Field of the Invention [0001]
  • This invention relates generally to silicone films, and more specifically to application of such films to glass and other surfaces. [0002]
  • 2. Description of the Prior Art [0003]
  • Various methods exist for manufacturing easily cleanable, water repellent glass products, including shower doors, windshields, glass entry doors and glass partitions in restaurants. Two such methods are disclosed in U.S. Pat. Nos. 5,415,927 to Hirayama et el. and 4,263,350 to Valimont. [0004]
  • In another method currently in use, the glass is coated with a film consisting of chains of silicone molecules, with each chain chemically bound at one end to the surface of the glass. Each chain contains from dozens to hundreds of dimethylsiloxane (DMS) units and is terminated at its free end by either a hydroxyl (OH) group or a chlorine attached to a silicon, which soon reacts with water vapor in the air to produce OH groups. This existing film is in use on a number of glass products as well as other silica-containing products such as granite, porcelain, earthenware and stoneware, and for the most part, has performed satisfactorily. However, the water-repellence of the film is limited to some extent by the presence of the terminal OH groups, which are highly water-attracting. [0005]
  • Accordingly, it is an object of the present invention to improve the water-resistance of silicone films on glass, and to provide a support film for chemically active substances. [0006]
  • Another object of the invention is to produce a family of silicone films for treating a variety of products such as the silica-containing products previously mentioned as well as organic substances including paper, cotton, nylon, leather, and wood, in order to improve the surface properties of those products. [0007]
  • SUMMARY OF THE INVENTION
  • Briefly, to achieve the desired objects of the instant invention in accordance with the preferred embodiments thereof, a silicone film is attached to a surface by chemical bonding. The silicone film consists of chains of siloxane groups, each chain terminating in an end molecule which is either an ester, an ether, or a halogen. The end molecule is allowed to react with water, either water vapor in the surrounding air or by covering the surface with liquid water, to produce an end OH group. The surface is then contacted with a capping agent which reacts with the OH group to produce a new end group which improves the properties of the film. [0008]
  • The specific improvement in properties will depend on the siloxane groups used, as well as the composition of the capping agent. In general, the siloxane groups have the formula [0009]
    Figure US20010018130A1-20010830-C00001
  • and the capping agent has the formula [0010]
    Figure US20010018130A1-20010830-C00002
  • For water-repellent applications, R consists of nonpolar groups, and R[0011] 1 consists of inert groups. For non-water-repellent applications, R consists of polar or nonpolar groups. In other applications, R1 could consist of chemically active groups, enabling the surface to be used as a solid state ion exchanger or an attachment point for chemically bound enzymes, chelating agents, dyes, chemical indicators or other substances.
  • BRIEF DESCRIPTION OF THE DRAWINGS
  • The foregoing and further and more specific objects and advantages of the instant invention will become readily apparent to those skilled in the art from the following detailed description of the preferred embodiments thereof taken in conjunction with the drawings in which: [0012]
  • FIG. 1 is a diagrammatic representation of a surface coated with a prior art water-repellent film; and [0013]
  • FIG. 2 is a diagrammatic representation of a surface coated with a water-repellent film manufactured using the process of the present invention. [0014]
  • DETAILED DESCRIPTION OF THE INVENTION
  • Turning now to the drawings, attention is first directed to FIG. 1, which shows a surface G which has been treated with a water-repellent film using a prior art process. In the most widely-used application of the process, the surface G is glass, but the process may actually be used to treat any surface containing OH or nitrogen hydrogen bonds, such as silica-containing surfaces including granite, porcelain, earthenware and stoneware, as well as organic substances including cotton, paper, nylon, leather and others. The film comprises chains of dimethylsiloxane (DMS) groups. Each chain is chemically bonded at one end to an oxygen (O) molecule, which in turn is chemically bonded to the surface G. The opposite end of each chain includes either a hydroxyl (OH) group or a chlorine attached to silicone, which will soon react with water vapor in the surrounding air to produce an OH group. [0015]
  • The process by which the film of FIG. 1 is created is as follows. Initially, the surface G is moistened. The moistened surface can be represented as shown in simplified form below: [0016]
    Figure US20010018130A1-20010830-C00003
  • In reality, however, the number of [0017]
    Figure US20010018130A1-20010830-C00004
  • molecules at the surface would be much greater than the number of O—H groups on the surface (a ratio of about 100:1). [0018]
  • Next, the surface is treated with dimethyldichlorosilane using Portable Vapor machines which may be adapted to fixed site chambers for large volume operations, or by using a wipe-on method or a dipping or spraying procedure. Where necessary, cyclohexylamine is used as a primer to ensure sufficient moisture for the chemical reaction to take place. After the dimethyldichlorosilane has been applied, a dimethyldichlorosilane molecule approaches an O—H group at the surface, as shown below: [0019]
    Figure US20010018130A1-20010830-C00005
  • The ensuing reaction results in an anchor molecule which will chemically bond the film to the surface G, as shown below: [0020]
    Figure US20010018130A1-20010830-C00006
  • The Si—Cl bond then reacts with water absorbed on the surface G as follows: [0021]
    Figure US20010018130A1-20010830-C00007
  • resulting in the following structure: [0022]
    Figure US20010018130A1-20010830-C00008
  • This structure then reacts with a DMS molecule as follows: [0023]
    Figure US20010018130A1-20010830-C00009
  • resulting in the molecule shown below: [0024]
    Figure US20010018130A1-20010830-C00010
  • The process of steps (c)-(f) above is repeated about 100 times until no more water remains for steps (c) and (d). The product has the formula: [0025]
    Figure US20010018130A1-20010830-C00011
  • where n is around 100 or more. The groups in the brackets are highly water repellent. However, the chlorine atom at the end of the chain slowly reacts over several hours with water vapor in the air to result in a product having the formula: [0026]
    Figure US20010018130A1-20010830-C00012
  • which is equivalent to the structure shown in FIG. 1. The Si—O—H group at the end of this final product is water-attracting, thus reducing the overall water repellence of the entire film, and creating a site for undesirable chemical reactions. [0027]
  • In the improved process of the instant invention, a surface coated with the above film is then treated with trimethylchlorosilane, which reacts with the OH group at the end of the DMS chain to produce trimethylchlorosiloxane (TMS). The final product is a film having the formula: [0028]
    Figure US20010018130A1-20010830-C00013
  • which is equivalent to the structure shown in FIG. 2. Because the TMS group at the end of the chain is chemically inert, the water-resistance of the film is much greater than that of the prior art film. [0029]
  • The silicone film produced by the process of steps (a)-(i) above is one specific example of the invention, intended for water-repellent applications. In a more general case, the moistened surface G is first contacted with silane groups having the formula [0030]
    Figure US20010018130A1-20010830-C00014
  • wherein R represents polar or nonpolar groups including hydrocarbons or halogenated hydrocarbons, and X is selected from the group consisting of esters, ethers, and halogens. The silane groups then react with the OH or nitrogen hydrogen bonds and water at the surface G to chemically bond the film to the surface G, in a process analogous to step (b) above. A series of reactions analogous to those shown in steps (b)-(f) above results in a polymer having the formula: [0031]
    Figure US20010018130A1-20010830-C00015
  • where n is around 100 or more. The X atom at the end of the chain then reacts with water vapor in the surrounding air resulting in a molecule having the formula: [0032]
    Figure US20010018130A1-20010830-C00016
  • The surface is then contacted with a capping agent having the formula: [0033]
    Figure US20010018130A1-20010830-C00017
  • where R[0034] 1 may include any combination of inert and reactive groups. The capping agent reacts with the OH group at the end of the chain, resulting finally in a chain having the formula:
    Figure US20010018130A1-20010830-C00018
  • The properties of the film manufactured using this process will depend on the choice of R and R[0035] 1, and to a lesser extent, X. Choosing X from the chloro group gives the lowest material cost and gives a faster reaction time, while esters and ethers are less reactive but produce less troublesome coproducts and require different processing conditions.
  • In general, for water repellent applications, R consists of nonpolar groups and R[0036] 1 consists of chemically inert groups. If R consists of approximately 50% methyl groups and 50% phenyl groups, the abrasion-resistance of the film is improved. The abrasion-resistance of the film can also be improved by connecting the DMS chains with methyltrichlorosilane (which causes branched chains and additional ends). The methyltrichlorosilane would cause the chains to be tied together in a three-dimensional structure, which would resist abrasion better than a two-dimensional structure.
  • For non-water repellent applications, R consists of polar or nonpolar groups. If R[0037] 1 is selected from chemically reactive groups, the end molecule can provide an attachment point for enzymes, chelating agents, ion exchange elements, chemical indicators and other substances.
  • Various other modifications and variations to the embodiments herein chosen for purposes of illustration will readily occur to those skilled in the art. To the extent that such variations and modifications do not depart from the spirit of the invention, they are intended to be included within the scope thereof which is assessed only be a fair interpretation of the following claims. [0038]

Claims (40)

1. A process for treating a surface of a substrate G containing OH or nitrogen hydrogen bonds and surrounded by air, the process including the steps of:
a) moistening the surface with water;
b) contacting the surface with silane groups having the formula
Figure US20010018130A1-20010830-C00019
wherein
R represents polar or nonpolar groups including hydrocarbons or halogenated hydrocarbons, and
X is selected from the group consisting of esters, ethers, and halogens;
c) allowing the silane groups to react with the OH or nitrogen hydrogen bonds and water at the surface to create a film formed of chains having the formula
Figure US20010018130A1-20010830-C00020
wherein n is around 100 or more;
d) allowing the X atom at the end of the chain to react with water to produce a molecule having the structure
Figure US20010018130A1-20010830-C00021
at the end of the chain; and
e) contacting the surface with a capping agent having the formula
Figure US20010018130A1-20010830-C00022
wherein R1 may include any combination of inert and reactive groups; and
f) allowing the capping agent to react with the molecule to result in a chain having the formula
Figure US20010018130A1-20010830-C00023
2. The process according to
claim 1
, wherein the substrate G includes silica molecules.
3. The process according to
claim 2
, wherein the substrate G is formed from a material selected from the group consisting of glass, ceramics and silica-containing minerals.
4. The process according to
claim 1
, wherein the substrate G includes organic molecules.
5. The process according to
claim 1
, wherein R is methyl.
6. The process according to
claim 1
, wherein R is selected from the group consisting of phenyl, ethyl, methyl, butyl, amyl, and larger alkyl groups.
7. The process according to
claim 1
, wherein R consists of 50% methyl groups and 50% phenyl groups, resulting in improved abrasion resistance of the film.
8. The process according to
claim 1
, wherein R consists of polar groups.
9. The process according to
claim 1
, wherein R consists of nonpolar groups.
10. The process according to
claim 1
, wherein R1 consists of chemically inert groups.
11. The process according to
claim 1
, wherein R1 consists of chemically reactive groups.
12. The process according to
claim 1
, wherein the step of contacting the surface with silane groups comprises chemically depositing the siloxane groups on the surface using a vapor machine.
13. The process according to
claim 1
, wherein the step of contacting the surface with silane groups comprises a wipe-on method.
14. The process according to
claim 1
, wherein the step of contacting the surface with silane groups comprises a dipping, or spraying procedure.
15. The process according to
claim 1
, wherein the step of moistening the surface comprises a step of priming the surface with cyclohexylamine.
16. A process for manufacturing water-resistant glass G in an environment including air, comprising the steps of:
a) coating the glass with a somewhat water-resistant film formed of chains having the formula
Figure US20010018130A1-20010830-C00024
wherein
R consists of nonpolar groups,
X is selected from the groups consisting of esters, ethers and halogens, and
n is around 100 or more,
the film being chemically bonded with the glass;
b) allowing the X atom at the end of the chain to react with water to produce a molecule having the structure
Figure US20010018130A1-20010830-C00025
at the end of the chain; and
c) contacting the surface with a capping agent having the formula
Figure US20010018130A1-20010830-C00026
wherein R1 consists of inert groups; and
d) allowing the capping agent to react with the molecule to result in a greatly water-resistant film formed from chains having the formula
Figure US20010018130A1-20010830-C00027
17. The process according to
claim 16
, wherein the somewhat water-resistant film comprises chains of dimethylsiloxane.
18. The process according to
claim 16
, wherein the capping agent is trimethylchlorosilane.
19. The process according to
claim 16
, wherein R is selected from the group consisting of phenyl, ethyl, methyl, butyl, amyl and larger alkyl groups.
20. The method according to
claim 16
, wherein R comprises approximately 50% methyl groups and 50% phenyl groups, resulting in improved abrasion-resistance of the highly water-resistant film.
21. A process for treating a surface of a substrate G containing OH or nitrogen hydrogen bonds and surrounded by air, the process including the steps of:
a) moistening the surface with water;
b) contacting the surface with silane groups having the formula
Figure US20010018130A1-20010830-C00028
wherein
R consists of polar or nonpolar groups, and
X is selected from the group consisting of esters, ethers and halogens;
c) allowing the silane groups to react with the OH or nitrogen hydrogen bonds and water at the surface to create a film formed of chains having the formula
Figure US20010018130A1-20010830-C00029
wherein
n is around 100 or more, and
the film is chemically bonded to the surface;
d) allowing the X atom at the end of the chain to react with water to produce a molecule having the structure
Figure US20010018130A1-20010830-C00030
at the end of the chain; and
e) contacting the surface with a capping agent having the formula
Figure US20010018130A1-20010830-C00031
wherein R1 consists of chemically active groups, and
f) allowing the capping agent to react with the molecule to result in a new end molecule having the formula
Figure US20010018130A1-20010830-C00032
wherein the new end molecule serves as a solid state ion exchanger or attachment point for chemically bound enzymes, chelating agents, dyes, chemical indicators, or the like.
22. The process according to
claim 21
, wherein the substrate G includes silica molecules.
23. The process according to
claim 22
, wherein the substrate G is formed from a material selected from the group consisting of glass, ceramics, and silica-containing minerals.
24. The process according to
claim 21
, wherein the substrate G includes organic molecules.
25. The process according to
claim 21
, wherein R is methyl.
26. The process according to
claim 21
, wherein the film consists of chains of dimethylsiloxane.
27. A film for altering the properties of a surface G containing OH or nitrogen hydrogen bonds and surrounded by air, the film consisting of a polymer including:
a) an anchor group having the formula
Figure US20010018130A1-20010830-C00033
wherein
R represents polar or nonpolar groups including hydrocarbons or halogenated hydrocarbons;
b) a chain of siloxane groups having a first end and a second end, the first end of the chain being chemically bound to the silicon molecule of the anchor group, the chain having the formula
Figure US20010018130A1-20010830-C00034
where n is around 100 or more; and
c) a terminal group of molecules chemically bound to the second end of the chain, the terminal group having the structure
Figure US20010018130A1-20010830-C00035
where R1 may include any combination of inert and reactive groups.
28. The film according to
claim 27
, wherein R1 is the same as R.
29. The film according to
claim 27
, wherein R is methyl.
30. The film according to
claim 27
, wherein R is selected from the group consisting of phenyl, ethyl, methyl, butyl, amyl, and larger alkyl groups.
31. The film according to
claim 27
, wherein R consists of polar groups.
32. The film according to
claim 27
, wherein R consists of nonpolar groups.
33. The film according to
claim 27
, wherein R1 consists of chemically inert groups.
34. The film according to
claim 27
, wherein R1 consists of chemically reactive groups.
35. In a process of manufacturing a water-resistant film for protecting a surface G containing OH or nitrogen hydrogen bonds wherein the process comprises the step of coating the glass with a polymer having
i) an anchor group having the formula
Figure US20010018130A1-20010830-C00036
wherein
R consists of nonpolar groups, and
ii) a chain of siloxane groups, the chain having a first end and a second end, the first end of the chain being chemically bound to the silicon molecule of the anchor group, the chain having the formula
Figure US20010018130A1-20010830-C00037
where n is around 100 or more, and
iii) a terminal group of molecules chemically bound to the second end of the chain, the terminal group having the formula
Figure US20010018130A1-20010830-C00038
wherein
R1 consists of inert groups, and
X is selected from the group consisting of esters, ethers and halogens, the improvement comprising the steps of
a) allowing the X atom of the terminal group to react with water to produce a new terminal group having the formula
Figure US20010018130A1-20010830-C00039
b) replacing the new terminal group with a final terminal group having the structure
Figure US20010018130A1-20010830-C00040
wherein R1 consists of inert groups.
36. The improvement according to
claim 35
, wherein the siloxane groups consist of dimethylsiloxane groups.
37. The improvement according to
claim 36
, wherein the final terminal group consists of a trimethylsiloxane group.
38. The improvement according to
claim 35
, wherein R1 is the same as R.
39. The improvement according to
claim 35
, wherein R is selected from the group consisting of phenyl, ethyl, methyl, butyl, amyl, and larger alkyl groups.
40. The improvement according to
claim 35
, wherein the step of replacing the new terminal group comprises the substeps of:
a) contacting the surface with a capping agent having the formula
Figure US20010018130A1-20010830-C00041
b) allowing the capping agent to react with the new terminal group to result in an inert final terminal group.
US09/803,280 1998-11-03 2001-03-09 Capped silicone film and method of manufacture thereof Abandoned US20010018130A1 (en)

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Publication number Priority date Publication date Assignee Title
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US9074778B2 (en) 2009-11-04 2015-07-07 Ssw Holding Company, Inc. Cooking appliance surfaces having spill containment pattern
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Families Citing this family (19)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6743516B2 (en) * 2000-09-29 2004-06-01 Guardian Industries Corporation Highly durable hydrophobic coatings and methods
DE10140246A1 (en) 2001-08-09 2003-03-06 Forsch Pigmente Und Lacke E V Process for treating surfaces of substrates
DE10140247A1 (en) * 2001-08-09 2003-03-06 Forsch Pigmente Und Lacke E V Process for coating substrate surfaces
US7202321B2 (en) * 2002-06-07 2007-04-10 The Boeing Company Method and composition for sealing components and components sealed thereby
US7910683B2 (en) * 2002-06-07 2011-03-22 The Boeing Company Tough and strongly-adherent anti-icing coatings
TWI319713B (en) * 2002-10-25 2010-01-21 Sustained-release tramadol formulations with 24-hour efficacy
US8487002B2 (en) * 2002-10-25 2013-07-16 Paladin Labs Inc. Controlled-release compositions
US7138186B2 (en) 2004-02-05 2006-11-21 Guardian Industries Corp. Hydrophobic coatings and methods
BRPI0615860B8 (en) * 2005-09-09 2021-05-25 Labopharm Barbados Ltd solid monolithic extended release pharmaceutical composition
AU2008314454A1 (en) * 2007-10-16 2009-04-23 Labopharm (Barbados) Limited Bilayer composition for the sustained release of acetaminophen and tramadol
BRPI0821732A2 (en) 2007-12-17 2015-06-16 Labopharm Inc Controlled release formulations, solid dosage form, and use of controlled release formulation
AU2009327312A1 (en) 2008-12-16 2011-08-04 Labopharm Europe Limited Misuse preventative, controlled release formulation
TWI439976B (en) * 2009-04-17 2014-06-01 Ind Tech Res Inst Method for isolating a flexible film from a substrate and method for fabricating an electric device
DE102009047351A1 (en) * 2009-12-01 2011-06-09 Evonik Goldschmidt Gmbh Composite silicone membranes with high separation efficiency
IT1400558B1 (en) * 2010-06-28 2013-06-14 Smart Space Solutions Srl GLASS GLAZING WITH ACTIVE SHIELDING
CN103145346A (en) * 2011-12-06 2013-06-12 中国科学院过程工程研究所 Method of modifying wetting performance of surfaces of smooth glasses and application thereof on surface modification of glass microchannels
AR096071A1 (en) 2013-04-24 2015-12-02 Diamon Fusion Int Inc METHOD FOR AUTOMATICALLY INTRODUCING REACTIVE LIQUID CHEMICAL AGENTS WITH THE AIR TO A SUBSTRATE IN A CLOSED DEPOSIT OF CHEMICAL VAPOR DEPOSIT, METHOD FOR PREPARING A DEHUMIDIFIED CARTRIDGE AND METHOD FOR GENERATING
KR102195254B1 (en) 2013-12-30 2020-12-28 삼성디스플레이 주식회사 Manufacturing method for display device
GR20220100627A (en) 2022-08-01 2024-03-12 Παπαδοπουλος Νικολαος-Ξαφακης Σωτηριος Ομορρυθμη Εταιρεια, Method of developing protective and easy-to-clean high-resistance nanocoating systems for multiple substrates

Family Cites Families (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2559259A1 (en) 1975-12-31 1977-07-14 Dynamit Nobel Ag SILANE WITH DISCONNECTED FUNCTIONAL GROUPS AS ADHESION MEDIA
US4263350A (en) 1979-12-31 1981-04-21 Ppg Industries, Inc. Silane release surfaces on glass
US4539061A (en) * 1983-09-07 1985-09-03 Yeda Research And Development Co., Ltd. Process for the production of built-up films by the stepwise adsorption of individual monolayers
JPH04185641A (en) * 1990-11-20 1992-07-02 Fujitsu Ltd Production of heat-resistant resin composition and insulation film
EP0511548B1 (en) * 1991-04-30 1997-07-09 Matsushita Electric Industrial Co., Ltd. Chemically adsorbed film and method of manufacturing the same
JP3007436B2 (en) * 1991-04-30 2000-02-07 松下電器産業株式会社 Siloxane-based molecular film
JPH0597478A (en) 1991-10-04 1993-04-20 Nippon Sheet Glass Co Ltd Water repellent glass article and its production
US5372851A (en) 1991-12-16 1994-12-13 Matsushita Electric Industrial Co., Ltd. Method of manufacturing a chemically adsorbed film
JP2804693B2 (en) * 1993-03-19 1998-09-30 松下電器産業株式会社 Siloxane-based surface treatment agent, its production method and its use
JPH06264051A (en) * 1993-03-15 1994-09-20 Matsushita Electric Ind Co Ltd Film for preventing ice and snow accretion and its production
US5723172A (en) 1994-03-11 1998-03-03 Dan Sherman Method for forming a protective coating on glass
US5665424A (en) 1994-03-11 1997-09-09 Sherman; Dan Method for making glass articles having a permanent protective coating
FR2722493B1 (en) 1994-07-13 1996-09-06 Saint Gobain Vitrage MULTI-LAYERED HYDROPHOBIC GLAZING
JPH09268281A (en) 1996-03-29 1997-10-14 Toray Dow Corning Silicone Co Ltd Water-repellent composition for motor vehicle glass and water-repellent glass for motor vehicle

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US9388325B2 (en) 2012-06-25 2016-07-12 Ross Technology Corporation Elastomeric coatings having hydrophobic and/or oleophobic properties

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