CA2663713A1 - Silane coating material and a process to produce silane coating - Google Patents
Silane coating material and a process to produce silane coating Download PDFInfo
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- CA2663713A1 CA2663713A1 CA002663713A CA2663713A CA2663713A1 CA 2663713 A1 CA2663713 A1 CA 2663713A1 CA 002663713 A CA002663713 A CA 002663713A CA 2663713 A CA2663713 A CA 2663713A CA 2663713 A1 CA2663713 A1 CA 2663713A1
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- Prior art keywords
- process according
- silane
- coating
- coating material
- silanes
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D4/00—Coating 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING 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
- C09D183/00—Coating compositions based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
Abstract
The invention relates to a silane coating material and to a method for the production of a silane coating. In order to create a silane coating material according to the generic term, in which the disadvantages stated above can be avoided, a method for the production of a silane coating according to the invention is proposed, wherein one or more silanes that are not, or are only slightly, pre-condensed, are added to a reaction partner and the resulting coating material is applied to a substrate and cured. Surprisingly it has been found that by means of the reaction of higher molecular and possibly slightly pre-cross-linked silanes and a suitable reaction partner a new class of coating materials can be created. According to prior art, silanes are processed via sol-gel processes, starting with pre-condensed species. The procedural method according to the invention is advantageous insofar as no restrictions exist with regard to the working life, and additionally improved properties of the coating material are achieved, particularly high scratch resistance.
Description
DESCRIPTION
Silane Coating Material and a Process to Produce Silane Coating "I'he invention relates to a silane coating material and a process to produce silane coating.
There are known silane coatings which are produced from silicone resins. These involve pre-condensing monomers, such as dimethyl siloxane or otherwise organically modified homologous species, until there are resins of high molecular weight. These can then be hardened with the usual commei-cial starters. Applications of such systems include coating, building protective agents, sealants, ctc.
To maintain these systems in a coatable form and to prevent gelation, silanes are generally utilized with two organically modified side chains.
These coating systems are highly temperature resistant, but usually only demonstrate moderate abrasion re~istance.
Three- and fourfold cross-linkable silanes are made into a processible form in the sol-gel process. VlWith this process silanes. such as tetraethoxysilane (TEOS) or methyltriethoxysilane (MTEOS), but also organically modihed silanes, such as glycidoxypropyltriethoxysilane (GPTES, Glyeo) or methacrylpropyltrimethoxysilane (MPTS) etc., are hydrolized and pre-condensed in the presence of a catalyst. This creates a coatable sol. which can be applied to a surface as coating following application and hardening.
This results in additional organic linking and the coatings are generally scratch-resistant as well as highly cross-linkable and resistant against chemicals.
However, during the synthesis low-molecular alcohols, such as methanol and ethanol, are created which exhibit a low flash point and are difficult to remove. As described in DE 198 16 136 A1, these can be removed or separated by phase separation, as described in DE 100 63 519 Al.
Another issue is the limited pot life i-esulting from the unconti-olled continuation of the condensation reactions.
Silane Coating Material and a Process to Produce Silane Coating "I'he invention relates to a silane coating material and a process to produce silane coating.
There are known silane coatings which are produced from silicone resins. These involve pre-condensing monomers, such as dimethyl siloxane or otherwise organically modified homologous species, until there are resins of high molecular weight. These can then be hardened with the usual commei-cial starters. Applications of such systems include coating, building protective agents, sealants, ctc.
To maintain these systems in a coatable form and to prevent gelation, silanes are generally utilized with two organically modified side chains.
These coating systems are highly temperature resistant, but usually only demonstrate moderate abrasion re~istance.
Three- and fourfold cross-linkable silanes are made into a processible form in the sol-gel process. VlWith this process silanes. such as tetraethoxysilane (TEOS) or methyltriethoxysilane (MTEOS), but also organically modihed silanes, such as glycidoxypropyltriethoxysilane (GPTES, Glyeo) or methacrylpropyltrimethoxysilane (MPTS) etc., are hydrolized and pre-condensed in the presence of a catalyst. This creates a coatable sol. which can be applied to a surface as coating following application and hardening.
This results in additional organic linking and the coatings are generally scratch-resistant as well as highly cross-linkable and resistant against chemicals.
However, during the synthesis low-molecular alcohols, such as methanol and ethanol, are created which exhibit a low flash point and are difficult to remove. As described in DE 198 16 136 A1, these can be removed or separated by phase separation, as described in DE 100 63 519 Al.
Another issue is the limited pot life i-esulting from the unconti-olled continuation of the condensation reactions.
The purpose of the invention is thus to create a silane coating production process according to the preamble, in which the disadvantages described above are avoided.
According to the invention this objective is accoinplished with a process to produce a silane coating where one or several non-pre-condensed silanes with a molecular mass greater than 300 undergo an organic linking reaction with homologous or non-honlologous silanes or with organic monomers, oligomers or polymers, charged with a reactant consisting of 0.5 to 50 weight by percent Lewis acids and the thus produced coating nlaterial is applied to a substrate and hardened.
Surprisingly it has been shown that through the reaction involving higher-molecular and only slightly pre-cross-linked silanes with a suitable reactant a new class of coating materials can be created. According to the current state of the art. silanes are processed in so]-gel processes, where pre-condensed species are assumed. The approach according to the invention, in which a pre-condensation reaction is mostly or completely avoided, is advantageous in that there are no restrictions with respect to pot time and. additionally, better features of the coating material are obtained, particularly a high scratch-resistance.
The organic cross linking reaction is understood as an organic linking of two silanes or between silanes and organic molecules via the organic functions, producing silanes of greater molecular weight.
According to the invention, the niolecular mass of the silane(s) should be greater than 500 and most preferably greater than 1,000.
It is important for the molecular weight of the silanes to be high so that the reaction can be started on a surface without the uncondensed silanes evaporating.
This invention includes that the silane(s) exhibit polarized groups in organic side chains. which are suitable for the formation of hydrogen bonds.
Also, according to the invention, the vapor pressure of the silane(s) is lower than 2, preferably lower than 1 and most preferably lower than 0.5 hPa at 20 C.
It is possible, for example, that the silane(s) are isocyanosilanes pre-cross linked with diols or polyols.
In this context the organic molecular mass is pi-eferably greater than the inorganic.
As silancs, especially the following can be considered: 3-aminopropyltriethoxysilane, aminoeth5 laminpropyltrimethoxysilane, aminoethylanlinopropyltrimethoxysilane, aminoeth} laminopropylsilane, 3-aminopropyltrirnethoxysilane, N-(2-aminoethyle)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aniinopropylmethyldimethoxysilane. N-(2-aminoeth) l)-3-aminopropylmethyldimethoxysilane, N cyclohexyl 3 aminop-opyl trimethoxvsilane, benzylaminoethylaminopropyltrimethoxysilane.
vinylbenzylamino-ethylaminopropyltrimethoxysilane. vinyltrimethoxysilane, vinyltriethoxysilane, vinyldimethoxymethylsilane. vinyl(tris)rnethoxyethoxy)silane, vinylmethoxymethylsilane, vinyltris(2-methoxyethoxy)silane. vinyltriacetoxysilane.
chloropropyltrimethoxysilane. 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane glycidoxypropyl-methyldietlloxysilane. mercaptopropyl-trimethoxysilane, bis-triethoxvsilylpropyldisulfidosilane, bis-triethoxysilyl-propyldisulfidosilane, bis-triethoxysilylpropyltetroasulfidosilane. N-cyclohexylaminomethylmethyldiecthoxysilane. n-cyclohexylaminomethyltriethoxysilane, n-phenylaminomethyltrimethoxysilane. (methacryloxymethyl)methyldimethoxysilane.
methacryl-oxymethyltrimethoxysilane, (methacryloxymethyl)methyldiethoxysilane, methacryloxymethyl-triethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacr\,loxypropyltriacetoxysilane, (isocyanatomethyl)methyldimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-trimethoxysilylmethyl-O-methylcarbamat, n-dimethoxy-(methyl)silylmethyl-O-methyl-carbamat. 3-(triethoxysilyl)propyl succinic anhydride.
According to the invention this objective is accoinplished with a process to produce a silane coating where one or several non-pre-condensed silanes with a molecular mass greater than 300 undergo an organic linking reaction with homologous or non-honlologous silanes or with organic monomers, oligomers or polymers, charged with a reactant consisting of 0.5 to 50 weight by percent Lewis acids and the thus produced coating nlaterial is applied to a substrate and hardened.
Surprisingly it has been shown that through the reaction involving higher-molecular and only slightly pre-cross-linked silanes with a suitable reactant a new class of coating materials can be created. According to the current state of the art. silanes are processed in so]-gel processes, where pre-condensed species are assumed. The approach according to the invention, in which a pre-condensation reaction is mostly or completely avoided, is advantageous in that there are no restrictions with respect to pot time and. additionally, better features of the coating material are obtained, particularly a high scratch-resistance.
The organic cross linking reaction is understood as an organic linking of two silanes or between silanes and organic molecules via the organic functions, producing silanes of greater molecular weight.
According to the invention, the niolecular mass of the silane(s) should be greater than 500 and most preferably greater than 1,000.
It is important for the molecular weight of the silanes to be high so that the reaction can be started on a surface without the uncondensed silanes evaporating.
This invention includes that the silane(s) exhibit polarized groups in organic side chains. which are suitable for the formation of hydrogen bonds.
Also, according to the invention, the vapor pressure of the silane(s) is lower than 2, preferably lower than 1 and most preferably lower than 0.5 hPa at 20 C.
It is possible, for example, that the silane(s) are isocyanosilanes pre-cross linked with diols or polyols.
In this context the organic molecular mass is pi-eferably greater than the inorganic.
As silancs, especially the following can be considered: 3-aminopropyltriethoxysilane, aminoeth5 laminpropyltrimethoxysilane, aminoethylanlinopropyltrimethoxysilane, aminoeth} laminopropylsilane, 3-aminopropyltrirnethoxysilane, N-(2-aminoethyle)-3-aminopropyltrimethoxysilane, N-(2-aminoethyl)-3-aniinopropylmethyldimethoxysilane. N-(2-aminoeth) l)-3-aminopropylmethyldimethoxysilane, N cyclohexyl 3 aminop-opyl trimethoxvsilane, benzylaminoethylaminopropyltrimethoxysilane.
vinylbenzylamino-ethylaminopropyltrimethoxysilane. vinyltrimethoxysilane, vinyltriethoxysilane, vinyldimethoxymethylsilane. vinyl(tris)rnethoxyethoxy)silane, vinylmethoxymethylsilane, vinyltris(2-methoxyethoxy)silane. vinyltriacetoxysilane.
chloropropyltrimethoxysilane. 3-glycidoxypropyltrimethoxysilane, 3-glycidoxypropyltriethoxysilane glycidoxypropyl-methyldietlloxysilane. mercaptopropyl-trimethoxysilane, bis-triethoxvsilylpropyldisulfidosilane, bis-triethoxysilyl-propyldisulfidosilane, bis-triethoxysilylpropyltetroasulfidosilane. N-cyclohexylaminomethylmethyldiecthoxysilane. n-cyclohexylaminomethyltriethoxysilane, n-phenylaminomethyltrimethoxysilane. (methacryloxymethyl)methyldimethoxysilane.
methacryl-oxymethyltrimethoxysilane, (methacryloxymethyl)methyldiethoxysilane, methacryloxymethyl-triethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacryloxypropyltrimethoxysilane, 3-methacr\,loxypropyltriacetoxysilane, (isocyanatomethyl)methyldimethoxysilane, 3-isocyanatopropyltrimethoxysilane, 3-trimethoxysilylmethyl-O-methylcarbamat, n-dimethoxy-(methyl)silylmethyl-O-methyl-carbamat. 3-(triethoxysilyl)propyl succinic anhydride.
In the context of this invention the water content should be a maximum of 5 %, preferably 1% and most preferably the reaction should occur without the presence of water.
Air humidity generally does not interfere with the reaction.
Furthermore, according to the design, the silane(s) should be pre-cross-linked at a maximuin of 5 %, preferably 1% and most preferably not inorganically pre-cross-linked.
It is also part of the invention that up to 20 weight per cent Lewis acids or Lewis bases bc utilized as reactants, especially in the form of transition metal cotnplexes.
salts or particles.
preferably micro- or nano-particles.
In this context the transition metal complexes. salts or particles should preferably be titanium.
aluminum, tin or zirconium complexes.
It can also be provided that particles, especially micro-, sub-micro- or nano-particles be added as fillers.
A design of the invention involves the addition of solvents, especially alcohol. acetates, ether or reacting diluents.
Additionally, the invention entails that the coating material is hardened after application at temperatures from room temperature up to 1,200 C, preferably from room temperature up to 250 C, with the hardening preferably being done thermally, by microwave radiation or UV
radiation.
Silane coating, produced by a process according to the invention, is also included in the invention.
Furthermore, scratch-resistance, anti-corrosion, easy-to-clean, anti-fingerprint. anti-reflex, anti-fogging, scaling protection, diffusion barrier, radiation protection coating or as self-cleaning, anti-bacterial, anti-microbial, tribological and hydrophilic coating is pai-t of the invention.
The following embodiments provide further details about the invention.
Embodiment I :
11.8 g hexanediole are warmed ,vith 49.5 g ICTES (isocyanatopropyltriethox)-silane) while stirring to 50 C and charged with 0.1 g dibutyltin dilaurate. Stirring continues for 30 min. at 50 C followed by cooling down to room temperature.
Air humidity generally does not interfere with the reaction.
Furthermore, according to the design, the silane(s) should be pre-cross-linked at a maximuin of 5 %, preferably 1% and most preferably not inorganically pre-cross-linked.
It is also part of the invention that up to 20 weight per cent Lewis acids or Lewis bases bc utilized as reactants, especially in the form of transition metal cotnplexes.
salts or particles.
preferably micro- or nano-particles.
In this context the transition metal complexes. salts or particles should preferably be titanium.
aluminum, tin or zirconium complexes.
It can also be provided that particles, especially micro-, sub-micro- or nano-particles be added as fillers.
A design of the invention involves the addition of solvents, especially alcohol. acetates, ether or reacting diluents.
Additionally, the invention entails that the coating material is hardened after application at temperatures from room temperature up to 1,200 C, preferably from room temperature up to 250 C, with the hardening preferably being done thermally, by microwave radiation or UV
radiation.
Silane coating, produced by a process according to the invention, is also included in the invention.
Furthermore, scratch-resistance, anti-corrosion, easy-to-clean, anti-fingerprint. anti-reflex, anti-fogging, scaling protection, diffusion barrier, radiation protection coating or as self-cleaning, anti-bacterial, anti-microbial, tribological and hydrophilic coating is pai-t of the invention.
The following embodiments provide further details about the invention.
Embodiment I :
11.8 g hexanediole are warmed ,vith 49.5 g ICTES (isocyanatopropyltriethox)-silane) while stirring to 50 C and charged with 0.1 g dibutyltin dilaurate. Stirring continues for 30 min. at 50 C followed by cooling down to room temperature.
5 g adduct (see above) is dissolved in 10 g l-methoxy-2-propanol and charged with 0.2 g aluminium acetylacetonate.
After application (e.g. flooding) onto a polycarbonate panel, hardening is performed for 50 min.
at 120 C in a circulating air oven.
The resulting coating exhibits excellent scratch-resistance.
Embodiment 2 :
30.0 g desniophen 1145 is warmed with 4.3 g ICTES
(isocyanatopropyltriethoxysilane) while stirring to 50 C and charged with 0.15 g dibutyltin dilaurate. Stirring continues for 1 h at 50 C
followed by cooling down to room temperature.
After application (e.g. flooding) onto a polycarbonate panel, hardening is performed for 50 min.
at 120 C in a circulating air oven.
The resulting coating exhibits excellent scratch-resistance.
Embodiment 2 :
30.0 g desniophen 1145 is warmed with 4.3 g ICTES
(isocyanatopropyltriethoxysilane) while stirring to 50 C and charged with 0.15 g dibutyltin dilaurate. Stirring continues for 1 h at 50 C
followed by cooling down to room temperature.
g resultant (see above) is dissolved in 8 g 1-methoxy-2-propanol and charged with 0.1 g alunlinium acetylacetonate.
Sheet iron is coated with the resulting coating solution using spray application and then hardened at 150 C for 60 min. in a circulating air oven.
The layers exhibit high scratch and corrosion resistance.
L;mbodiment 3 :
22.1 g anlinopropyltriethoxysilane is stirred with 27.8 g glyeidoxypropyltriethoxysilane at 45 C and left at that tempei-ature for 45 min.
10 g of the reactive mixture is dissolved in 12 g isopropanol and charged with 0.3 g acetyl aceton.
Altei- Ilooding on aluminum plates the coats arc hardened at 120 C for 20 min. in a circulating air oven.
'I'he coats cxhibit high scratch and corrosion resistance.
Embodiment 4 :
24.8 g 3-methoxypropyltriethoxysilane is dissolved in 12 g 1-methoxy-2-propanol and charged with 2.5 g ebecryl 1259 and 2.0 g desnlodur N 3300 and tetnpered at 40 C for 2 h. Then 0.24 g zirconium acetylacetonate is added to the mixture. -I'he mixture is applied to a PMMA panel by llooding and irradiated with approx. 2.5 .1/cm2 with a Hg medium pressure lamp and subsequently tempered for 2 h at 80 C.
"1'he layers exhibit high scratch and abrasion resistance and/or cheniical resistance to acids and bases.
Sheet iron is coated with the resulting coating solution using spray application and then hardened at 150 C for 60 min. in a circulating air oven.
The layers exhibit high scratch and corrosion resistance.
L;mbodiment 3 :
22.1 g anlinopropyltriethoxysilane is stirred with 27.8 g glyeidoxypropyltriethoxysilane at 45 C and left at that tempei-ature for 45 min.
10 g of the reactive mixture is dissolved in 12 g isopropanol and charged with 0.3 g acetyl aceton.
Altei- Ilooding on aluminum plates the coats arc hardened at 120 C for 20 min. in a circulating air oven.
'I'he coats cxhibit high scratch and corrosion resistance.
Embodiment 4 :
24.8 g 3-methoxypropyltriethoxysilane is dissolved in 12 g 1-methoxy-2-propanol and charged with 2.5 g ebecryl 1259 and 2.0 g desnlodur N 3300 and tetnpered at 40 C for 2 h. Then 0.24 g zirconium acetylacetonate is added to the mixture. -I'he mixture is applied to a PMMA panel by llooding and irradiated with approx. 2.5 .1/cm2 with a Hg medium pressure lamp and subsequently tempered for 2 h at 80 C.
"1'he layers exhibit high scratch and abrasion resistance and/or cheniical resistance to acids and bases.
Claims (17)
1. Process to produce a silane coating characterized by one or several non-pre-condensed silanes with a molecular mass greater than 300 undergoing an organic linking reaction with homologous or non-homologous silanes or with organic monomers. oligomers or polymers, charged with a reactant consisting of 0.5 to weight by percent Lewis acids and the thus produced coating material being applied to a substrate and hardened.
2. Process according to Claim 1 characterized by the molecular mass of the silane(s) being greater than 500 and most preferably greater than 1,000.
3. Process according to Claim 2 characterized by the silane(s) exhibiting polarized groups in organic side chains, which are suitable for the formation of hydrogen bonds.
4. Process according to Claim 1, characterized by the vapor pressure of the silane(s) being less than 2. preferably less than 1 and most preferably less than 0.5 hPa at 20°C.
5. Process according to Claim 1 characterized by the organic molecular mass being greater than the inorganic.
6. Process according to Claim 1 characterized by the water content being a maximum of %, preferably a maximum of 1% and most preferred that the reaction occur without the presence of any water.
7. Process according to Claim 1 characterized by the silane(s) being pre-cross linked at a maximum of 5 %, preferably 1 % and most preferably not being inorganically pre-cross linked.
8 8. Process according to Claim 1 characterized by reactants up to 20 weight per cent Lewis acids or Lewis bases, especially in form of transition metal complexes, salts or particles, with preferably micro- or nano-particles being utilized.
9. Process according to Claim 8 characterized by transition metal complexes, salts or particles being preferably titanium, aluminum, tin or zirconium complexes.
10. Process according to Claim 1 characterized by particles, especially micro-, sub-micro-or nano-particles, being added as fillers.
11. Process according to Claim 1 characterized by the addition of solvents, especially alcohol, acetates, ether or reacting diluents.
12. Process according to Claim 1 characterized by the addition of dulling substances, linkage dispersing agents, antifoaming agents, waxes, biocides, preservative agents or pigments.
13. Process according to Claim 1 characterized by the wet-chemical application of the coating material onto a substrate, particularly by spraying, immersion, flooding, rolling, painting or otherwise by vacuum evaporation.
14. Process according to Claim 13 characterized by the substrate being made of metal, synthetic, ceramic, lacquer, textile or a natural substance, such as wood or leather, glass, mineral substances or composite materials.
15. Process according to Claim 13 characterized by the coating material being hardened after application at temperatures from room temperature up to 1,200 °C, preferably from room temperature up to 250 °C, with the hardening preferably being done thermally by microwave or UV radiation.
16. Silane coating produced by a process according to Claims 1 through 15.
17. Use of coating according to Claim 16 as scratch-resistance, anti-corrosion, easy-to-clean, anti-fingerprint, anti-reflex, anti-fogging, scaling protection, diffusion barrier, radiation protection coating or as self-cleaning, anti-bacterial, anti-microbial, tribological and hydrophilic coating.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102006044310A DE102006044310A1 (en) | 2006-09-18 | 2006-09-18 | Silane coating material and method of making a silane coating material |
| DE102006044310.1 | 2006-09-18 | ||
| PCT/DE2007/001602 WO2008034409A2 (en) | 2006-09-18 | 2007-09-10 | Silane coating material and method for the production of a silane coating |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA2663713A1 true CA2663713A1 (en) | 2008-03-27 |
Family
ID=39104990
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA002663713A Abandoned CA2663713A1 (en) | 2006-09-18 | 2007-09-10 | Silane coating material and a process to produce silane coating |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US20090326146A1 (en) |
| EP (2) | EP2064293A2 (en) |
| JP (2) | JP5419693B2 (en) |
| KR (1) | KR101407162B1 (en) |
| CN (2) | CN102533103A (en) |
| CA (1) | CA2663713A1 (en) |
| DE (1) | DE102006044310A1 (en) |
| RU (2) | RU2441894C2 (en) |
| WO (1) | WO2008034409A2 (en) |
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| DE102006044310A1 (en) * | 2006-09-18 | 2008-03-27 | Nano-X Gmbh | Silane coating material and method of making a silane coating material |
| DE102007020404A1 (en) * | 2006-09-18 | 2008-10-30 | Nano-X Gmbh | Process for the preparation of a coating material |
| KR101013413B1 (en) * | 2008-01-07 | 2011-02-14 | 한국과학기술연구원 | Method for the fabrication of transparent gas barrier film using plasma surface treatment |
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| DE102011054615A1 (en) * | 2011-10-19 | 2013-04-25 | Nano-X Gmbh | Process for producing hardenable materials |
| WO2013060767A2 (en) | 2011-10-27 | 2013-05-02 | Dsm Ip Assets B.V. | Polymer, compositions and process for preparing them |
| SE1151043A1 (en) * | 2011-11-07 | 2013-05-08 | Hwq Relining Systems Aktiebolag | Coating a pipe or pipe system with a polymeric material |
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| WO2013189882A2 (en) * | 2012-06-20 | 2013-12-27 | Evonik Industries Ag | Coating agent having high scratch resistance |
| KR20140069801A (en) * | 2012-11-30 | 2014-06-10 | 삼성전자주식회사 | Mutifunctional coating structure and forming method for the same |
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- 2007-09-10 EP EP07801334A patent/EP2064293A2/en not_active Withdrawn
- 2007-09-10 CN CN2011104452004A patent/CN102533103A/en active Pending
- 2007-09-10 US US12/311,064 patent/US20090326146A1/en not_active Abandoned
- 2007-09-10 RU RU2009114821/05A patent/RU2441894C2/en not_active IP Right Cessation
- 2007-09-10 CN CN2007800381976A patent/CN101589117B/en not_active Expired - Fee Related
- 2007-09-10 WO PCT/DE2007/001602 patent/WO2008034409A2/en active Application Filing
- 2007-09-10 CA CA002663713A patent/CA2663713A1/en not_active Abandoned
- 2007-09-10 KR KR1020097007992A patent/KR101407162B1/en not_active IP Right Cessation
- 2007-09-10 EP EP11173058A patent/EP2383312A1/en not_active Withdrawn
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2011
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- 2011-10-18 RU RU2011142123/05A patent/RU2011142123A/en not_active Application Discontinuation
- 2011-10-25 JP JP2011234120A patent/JP2012066243A/en active Pending
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| RU2441894C2 (en) | 2012-02-10 |
| DE102006044310A1 (en) | 2008-03-27 |
| EP2383312A1 (en) | 2011-11-02 |
| JP2010503519A (en) | 2010-02-04 |
| RU2011142123A (en) | 2013-04-27 |
| JP5419693B2 (en) | 2014-02-19 |
| US20120029143A1 (en) | 2012-02-02 |
| CN101589117A (en) | 2009-11-25 |
| CN101589117B (en) | 2013-03-06 |
| WO2008034409A3 (en) | 2008-12-04 |
| RU2009114821A (en) | 2010-10-27 |
| KR20090055641A (en) | 2009-06-02 |
| WO2008034409A2 (en) | 2008-03-27 |
| KR101407162B1 (en) | 2014-06-13 |
| US20090326146A1 (en) | 2009-12-31 |
| EP2064293A2 (en) | 2009-06-03 |
| CN102533103A (en) | 2012-07-04 |
| JP2012066243A (en) | 2012-04-05 |
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