EP1704193A2 - Revetement hydrophile a base de polysilazane - Google Patents
Revetement hydrophile a base de polysilazaneInfo
- Publication number
- EP1704193A2 EP1704193A2 EP04803939A EP04803939A EP1704193A2 EP 1704193 A2 EP1704193 A2 EP 1704193A2 EP 04803939 A EP04803939 A EP 04803939A EP 04803939 A EP04803939 A EP 04803939A EP 1704193 A2 EP1704193 A2 EP 1704193A2
- Authority
- EP
- European Patent Office
- Prior art keywords
- polysilazane
- ionic
- coating
- reagent
- hydrophilic
- 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.)
- Withdrawn
Links
- 229920001709 polysilazane Polymers 0.000 title claims abstract description 53
- 238000000576 coating method Methods 0.000 title claims abstract description 43
- 239000011248 coating agent Substances 0.000 title claims abstract description 38
- 239000003153 chemical reaction reagent Substances 0.000 claims abstract description 34
- 239000000203 mixture Substances 0.000 claims abstract description 15
- 238000000034 method Methods 0.000 claims abstract description 12
- 150000003839 salts Chemical class 0.000 claims abstract description 7
- 229920000642 polymer Polymers 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000000129 anionic group Chemical group 0.000 claims abstract description 4
- BVKZGUZCCUSVTD-UHFFFAOYSA-N carbonic acid Chemical compound OC(O)=O BVKZGUZCCUSVTD-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000002091 cationic group Chemical group 0.000 claims abstract description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 4
- 239000001257 hydrogen Substances 0.000 claims abstract description 4
- 229910000077 silane Inorganic materials 0.000 claims abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims abstract 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 22
- 239000002904 solvent Substances 0.000 claims description 11
- 239000000654 additive Substances 0.000 claims description 9
- 239000011521 glass Substances 0.000 claims description 8
- 239000003973 paint Substances 0.000 claims description 8
- 230000005660 hydrophilic surface Effects 0.000 claims description 6
- 239000000463 material Substances 0.000 claims description 5
- 229920003023 plastic Polymers 0.000 claims description 5
- 239000004033 plastic Substances 0.000 claims description 5
- 238000009736 wetting Methods 0.000 claims description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 4
- 150000002148 esters Chemical class 0.000 claims description 3
- 150000002576 ketones Chemical class 0.000 claims description 3
- 229910052751 metal Inorganic materials 0.000 claims description 3
- 239000002184 metal Substances 0.000 claims description 3
- 239000011368 organic material Substances 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 230000008020 evaporation Effects 0.000 claims description 2
- 238000001704 evaporation Methods 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 239000003960 organic solvent Substances 0.000 claims description 2
- 229910017053 inorganic salt Inorganic materials 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 abstract description 5
- 239000000758 substrate Substances 0.000 description 14
- 239000000243 solution Substances 0.000 description 13
- -1 alkane polyol Chemical class 0.000 description 11
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 9
- 239000003795 chemical substances by application Substances 0.000 description 9
- 230000000694 effects Effects 0.000 description 8
- 239000010935 stainless steel Substances 0.000 description 8
- 229910001220 stainless steel Inorganic materials 0.000 description 8
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- 230000000996 additive effect Effects 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920000515 polycarbonate Polymers 0.000 description 5
- 239000004417 polycarbonate Substances 0.000 description 5
- 235000002639 sodium chloride Nutrition 0.000 description 5
- 238000001723 curing Methods 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- DURPTKYDGMDSBL-UHFFFAOYSA-N 1-butoxybutane Chemical compound CCCCOCCCC DURPTKYDGMDSBL-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical class OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 229920001577 copolymer Polymers 0.000 description 3
- 238000007598 dipping method Methods 0.000 description 3
- 230000001699 photocatalysis Effects 0.000 description 3
- 239000004408 titanium dioxide Substances 0.000 description 3
- JUWGUJSXVOBPHP-UHFFFAOYSA-B titanium(4+);tetraphosphate Chemical compound [Ti+4].[Ti+4].[Ti+4].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O JUWGUJSXVOBPHP-UHFFFAOYSA-B 0.000 description 3
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- RGHNJXZEOKUKBD-SQOUGZDYSA-M D-gluconate Chemical compound OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O RGHNJXZEOKUKBD-SQOUGZDYSA-M 0.000 description 2
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000919 ceramic Substances 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000008199 coating composition Substances 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940050410 gluconate Drugs 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical class CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 230000003287 optical effect Effects 0.000 description 2
- 229920000620 organic polymer Polymers 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 150000004756 silanes Chemical class 0.000 description 2
- 238000004528 spin coating Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 238000012360 testing method Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical class OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- GDCRYMZNGGCWEH-UHFFFAOYSA-N 3-trihydroxysilylpropanoic acid Chemical compound OC(=O)CC[Si](O)(O)O GDCRYMZNGGCWEH-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical class OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- 229910001335 Galvanized steel Inorganic materials 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 1
- 229920000877 Melamine resin Polymers 0.000 description 1
- BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004642 Polyimide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- HLCFGWHYROZGBI-JJKGCWMISA-M Potassium gluconate Chemical compound [K+].OC[C@@H](O)[C@@H](O)[C@H](O)[C@@H](O)C([O-])=O HLCFGWHYROZGBI-JJKGCWMISA-M 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 description 1
- 238000003848 UV Light-Curing Methods 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 238000005299 abrasion Methods 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 235000011054 acetic acid Nutrition 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000001476 alcoholic effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 229920000180 alkyd Polymers 0.000 description 1
- 150000001343 alkyl silanes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Chemical class OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 239000011449 brick Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005069 calcium Drugs 0.000 description 1
- 239000004227 calcium gluconate Substances 0.000 description 1
- 235000013927 calcium gluconate Nutrition 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 150000001983 dialkylethers Chemical class 0.000 description 1
- 230000009189 diving Effects 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- OUDSFQBUEBFSPS-UHFFFAOYSA-N ethylenediaminetriacetic acid Chemical compound OC(=O)CNCCN(CC(O)=O)CC(O)=O OUDSFQBUEBFSPS-UHFFFAOYSA-N 0.000 description 1
- 239000010419 fine particle Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 239000008397 galvanized steel Substances 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 125000002768 hydroxyalkyl group Chemical group 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 229920000592 inorganic polymer Polymers 0.000 description 1
- 150000008040 ionic compounds Chemical class 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 239000004310 lactic acid Chemical class 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 239000011777 magnesium Substances 0.000 description 1
- 229910052749 magnesium Inorganic materials 0.000 description 1
- 239000001630 malic acid Chemical class 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 239000004579 marble Substances 0.000 description 1
- 239000003550 marker Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- FQPSGWSUVKBHSU-UHFFFAOYSA-N methacrylamide Chemical compound CC(=C)C(N)=O FQPSGWSUVKBHSU-UHFFFAOYSA-N 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 239000003595 mist Substances 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920001515 polyalkylene glycol Polymers 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920000139 polyethylene terephthalate Polymers 0.000 description 1
- 239000005020 polyethylene terephthalate Substances 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000011148 porous material Substances 0.000 description 1
- 239000004224 potassium gluconate Substances 0.000 description 1
- 235000013926 potassium gluconate Nutrition 0.000 description 1
- 229960003189 potassium gluconate Drugs 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 230000005855 radiation Effects 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229910052709 silver Inorganic materials 0.000 description 1
- 239000004332 silver Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000000176 sodium gluconate Substances 0.000 description 1
- 235000012207 sodium gluconate Nutrition 0.000 description 1
- 229940005574 sodium gluconate Drugs 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- FYZFRYWTMMVDLR-UHFFFAOYSA-M trimethyl(3-trimethoxysilylpropyl)azanium;chloride Chemical compound [Cl-].CO[Si](OC)(OC)CCC[N+](C)(C)C FYZFRYWTMMVDLR-UHFFFAOYSA-M 0.000 description 1
- HRXKRNGNAMMEHJ-UHFFFAOYSA-K trisodium citrate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O HRXKRNGNAMMEHJ-UHFFFAOYSA-K 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
Classifications
-
- 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
- C09D183/16—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 in which all the silicon atoms are connected by linkages other than oxygen atoms
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C17/00—Surface treatment of glass, not in the form of fibres or filaments, by coating
- C03C17/28—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material
- C03C17/30—Surface treatment of glass, not in the form of fibres or filaments, by coating with organic material with silicon-containing compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C2217/00—Coatings on glass
- C03C2217/70—Properties of coatings
- C03C2217/75—Hydrophilic and oleophilic coatings
Definitions
- the present invention relates to a transparent, permanently hydrophilic coating based on polysilazane in combination with an ionic reagent to increase the hydrophilicity.
- Hydrophilic surfaces are characterized by good wettability with water, which is expressed measurably in a low contact angle. Such hydrophilic
- certain detergents are suitable for temporarily imparting hydrophilicity to surfaces.
- Such formulations have been available for a long time and are used, among other things. used as an anti-fog agent for glasses and optical devices, but these agents do not adhere to the surface and therefore only have an effect for a short time.
- EP-0498 005 A1 describes an aqueous / alcoholic formulation based on a vinylpyrrolidone / vinyl acetate copolymer which is used as an anti-fogging agent for spectacle lenses.
- hydrophilic coating materials consist of organic polymers or copolymers that contain polar groups. This
- Coatings are characterized by the fact that they are able to absorb water and thus the surface is wetted with a water film.
- a disadvantage of such coatings is their low abrasion resistance, moreover Due to the water absorption, the polymer swells, which causes the surface to dissolve or detach.
- either UV curing or temperature treatment is necessary for curing such polymeric systems, which on the one hand is associated with high technical outlay and thus on costs and on the other hand is not suitable for temperature-sensitive substrates.
- EP-0 339 909 B1 describes a thermally curable coating composition which contains polar copolymers which are composed of condensates of methacrylamide and further hydrophilic monomers. This formulation is applied to polycarbonate and PMMA and cured at 80-120 ° C.
- EP-1 118 646 A1 describes a UV-curable coating composition with anti-fogging properties based on polyalkylene oxide di (meth) acrylates, hydroxyalkyl (methacrylates) and alkane polyol poly (methacrylates), which is applied to polycarbonate plates, cured and leads to a reduction in fogging ,
- Fine-particle titanium dioxide particles in the anatase modification have photocatalytic properties and are also suitable for hydrophilically modifying surfaces.
- the photocatalytic effect and the associated hydrophilicity only occur when these particles are exposed to UV radiation, i.e. they are not suitable for indoor use.
- these particles tend to be organic
- EP-0 913447 A1 describes a formulation based on photocatalytically active nano-metal oxides which, when applied to a glass pane and after irradiation with UV light, shows no quality of fogging when breathed on.
- the adhesion of this anti-fog coating checked where, after erasing two or three times with an eraser, the coating can be completely removed.
- Silicate surfaces such as glass and ceramics or surfaces made of metal oxides can be coated with halogen or alkoxysilanes which carry hydrophilic substituents. These react with the oxidic surface and are thus covalently bound. Due to the chemical bond between the substrate and the silane, the hydrophilic substituents are permanently fixed on the surface and their effects are retained.
- No. 6,489,499 B1 describes a method for producing a hydrophilically modified glass surface, in which a solution of a siloxane-modified ethylene diamine tricarboxylic acid salt is used.
- no quantitative statement about the contact angle is made, but only that the wetting of a coated glass surface to which a drop of water is applied is better than without a coating.
- the disadvantage is that these silanes do not react with surfaces that do not contain oxide or hydroxide groups. For example, plastics, paints and resins cannot be given a hydrophilic effect with the aid of the hydrophilic silanes. Another disadvantage of this
- Hydrophilizing reagents are that because of their low molecular weight they diffuse into the substrate on strongly absorbent surfaces or surfaces with large pores without sufficiently covering the surface with a hydrophilic effect.
- Polysilazanes are suitable for the production of thin layers that can be used to protect substrates from scratches or corrosion, for example.
- WO 02/088269 A1 describes a dirt-repellent coating solution based on polysilazane, but without aftertreatment with a further hydrophilizing reagent. By coating a surface with polysilazane and then curing in air, relatively hydrophilic surfaces are already obtained which have a contact angle of 30-40 ° C.
- the object of the present invention was to develop an easy-to-use coating with which it is possible to provide a wide variety of materials such as glass, ceramics, metals, plastics, paints, resins and porous surfaces with a permanent hydrophilic effect.
- the invention therefore relates to a hydrophilic coating for surfaces containing one or more polysilazanes and an ionic reagent or mixtures of ionic reagents to increase the hydrophilicity.
- ionic reagents By applying ionic reagents to the polysilazane layer, charge is fixed on the substrate surface, which leads to a surface with high surface energy, which enables easy wetting with water. It is irrelevant whether the charge is a cationic or an anionic.
- Polysilazanes are very reactive inorganic or organic polymers. Thanks to their high reactivity, they adhere very well to a wide variety of surfaces by forming permanent chemical bonds and are also able to react chemically with other applied reagents, and thus these reagents as well bind permanently.
- the hydrophilic coating contains at least one polysilazane of the formula 1,
- the hydrophilizing agents are ionic compounds which are generally applied in solution to the polysilazane coating applied first, react with it and therefore permanently adhere to it. These can be a wide variety of reagents that enable the desired permanent hydrophilic effect in combination with the polysilazane coating.
- ionic hydrophilizing agents can be, for example
- Salts of carboxylic acids in particular of hydroxycarboxylic acids, such as calcium, sodium or potassium gluconate, salts of tartaric acid, citric acid, malic acid, lactic acid or sugar acid. Solutions of these salts can also be obtained directly by reacting the corresponding acid with lyes.
- Substituted ionic halogen-, hydroxy-, alkoxy- or alkylsilanes such as N- (trimethoxylsilylpropyl) ethylenediaminetriacetic acid, trisodium salt, N-trimethoxysilylpropyl-N, N, N-trimethylammonium chloride, N- (3-triethoxysilylpropyl) gluconyloxyl, grapplonyl amide ) -O- polyethylene oxide urethane, 1-trihydroxysilylpropionic acid disodium salt are suitable hydrophilizing agents.
- Ionic oligomers or polymeric compounds such as surfactants or dispersing additives such as Byk®-151, Byk®-LP N 6640, Anti-Terra®-203, Disperbyk®-140, Byk®-9076, Byk®-154, Disperbyk®, Disperbyk® -181 are also suitable hydrophilizing agents.
- Salts such as titanium phosphate which are similar to anatase Modification of titanium dioxide by irradiation with UV light can become "super-hydrophilic".
- titanium phosphate has the advantage over anatase that it is not so aggressive towards organic materials and does not destroy them.
- hydrophilization aids have in common that the contact angle of a surface coated with polysilazane is smaller than is observed without the use of these reagents.
- the invention further relates to a method for producing a hydrophilic coating comprising one or more polysilazanes and an ionic reagent or mixtures of ionic reagents, in which the coating of a surface with at least one polysilazane is carried out in a first step and then an ionic hydrophilizing reagent in a second step or a mixture of ionic hydrophilizing reagents can be applied in a solvent.
- Another object of the invention is a hydrophilic surface, obtainable by coating with the aforementioned polysilazanes and ionic hydrophilizing reagents.
- Suitable substrates include:
- Plastics such as Iron, stainless steel, galvanized steel, zinc, aluminum, nickel, copper, magnesium and their alloys, silver and gold, plastics, e.g. Polymethyl methacrylate, polyurethane, polycarbonate, polyesters such as polyethylene terephthalate, polyimides, polyamides, epoxy resins, ABS plastic, polyethylene, polypropylene, polyoxymethylene, porous mineral materials such as concrete, clay brick, marble, basalt,
- Paint surfaces such as plastic emulsion paints, acrylic paints, Epoxy paints, melamine resins, polyurethane resins and alkyd paints and organic materials such as wood, leather, parchment, paper and textiles glass,
- the coating with polysilazane can be carried out by wiping, dipping, spraying or spin-coating pure polysilazane or a polysilazane solution.
- a thin layer of polysilazane is necessary, which is transparent and therefore the optical appearance of the
- the layer thickness of the polysilazane layer is in the range from 0.01 to 10 micrometers, preferably 0.05 to 5 micrometers, particularly preferably 0.1 to 1 micrometers. It is possible to pretreat the surface to be coated with a primer first.
- the subsequent coating with the hydrophilizing agent can also be carried out by dipping, spraying, spin coating or wiping.
- Both the coating with polysilazane and the subsequent application of the ionic reagent are preferably carried out at a temperature in the range from 5 to 40 ° C., application at room temperature is particularly advantageous, which also enables the coating of temperature-sensitive substrates.
- the coating time can be shortened considerably.
- Particularly suitable solvents for polysilazane are organic solvents which contain no water and no reactive groups (such as hydroxyl or amine groups). These are, for example, aliphatic or aromatic hydrocarbons, halogenated hydrocarbons, esters such as ethyl acetate or butyl acetate, ketones such as acetone or methyl ethyl ketone, ethers such as tetrahydrofuran or dibutyl ether, and also mono- and polyalkylene glycol dialkyl ethers (Glymes) or mixtures of these solvents.
- organic solvents which contain no water and no reactive groups (such as hydroxyl or amine groups). These are, for example, aliphatic or aromatic hydrocarbons, halogenated hydrocarbons, esters such as ethyl acetate or butyl acetate, ketones such as acetone or methyl ethyl ketone, ethers such as tetrahydrofuran or dibutyl
- Another component of the polysilazane solution can be catalysts, such as tertiary amines, which accelerate the hardening of the polysilazane film or additives which facilitate the wetting of the background or film formation.
- catalysts such as tertiary amines
- Particularly suitable solvents for the hydrophilizing reagent are water, alcohols such as methanol, ethanol, isopropanol, ketones such as acetone or methyl ethyl ketone, carboxylic acids such as formic acid, acetic acid or propionic acid and esters such as ethyl acetate or butyl acetate or mixtures of these solvents.
- the coatings with polysilazanes were carried out in an inert gas atmosphere in a glove box.
- the various substrates were coated using a dipping apparatus.
- the contact angle measurements were carried out on a Krüss device.
- Perhydropolysilazane was used in various solvents as the polysilazane.
- Mixtures of xylene and pegasol (name NP) or di-n-butyl ether (name NL) are common. Manufacturer is Clariant Japan K.K.
- a polycarbonate disc (10 x 10 cm) was in a glove box with the help of a diving apparatus with a stepper motor at a speed of 20 cm / min. immersed in a 20% perhydropolysilazane solution in n-dibutyl ether. After a dwell time of 10 s, it was run at a speed of 20 cm / min. pulled out of the solution again. Allow to drain briefly and then take the sample out of the glove box. The sample is left in the air for 10 minutes and then immersed in an aqueous solution (10%) of the additive Byk-LP N-6640 (original solution is 40%, diluted 3: 1 with water). The sample is left in the solution for 24 hours and then rinsed off with water.
- the contact angle of water could not be determined exactly, but was clearly below 10 °.
- a stainless steel sample V2A was coated as described above.
- the aqueous solution of the Byk additive was heated to 50 ° C and the steel sample for 30 min. dipped.
- the contact angle of water was well below 10 °.
- a stainless steel sample was used as described in experiment 2. Instead of the Byk additive, the sample was immersed in an aqueous, saturated Ca gluconate solution. After 24 hours, a contact angle of less than 10 ° could be measured.
- a stainless steel sample was used as described in experiment 4.
- the saturated Ca gluconate solution was heated to 50 ° C. and the sample was stored for 30 minutes.
- the contact angle of water was well below 10 °.
- a stainless steel sample was used as described in experiment 2. Instead of the Byk additive, the sample was immersed in a 10% aqueous solution of the disodium salt of carboxyethylsilanetriol for 24 hours. The contact angle of water was less than 10 °.
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- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Wood Science & Technology (AREA)
- Geochemistry & Mineralogy (AREA)
- General Chemical & Material Sciences (AREA)
- Paints Or Removers (AREA)
- Application Of Or Painting With Fluid Materials (AREA)
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- Surface Treatment Of Glass (AREA)
- Chemical Treatment Of Metals (AREA)
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Abstract
L'invention concerne un revêtement hydrophile destiné à des surfaces, qui contient un ou plusieurs polysilazanes et un réactif ionique ou des mélanges de réactifs ioniques. Ce polysilazane est notamment un polysilazane de formule (1), (SiR'R"-NR"')n-, dans laquelle R', R", R" peuvent être identiques ou différents et représenter hydrogène ou des restes organiques ou organométalliques et n est calculé de sorte que le polysilazane présente un poids moléculaire moyen en nombre compris entre 150 et 150 000 g/mol. Dans un mode de réalisation préféré, le polysilazane est un perhydropolysilazane (R'=R"=R" = H). Le réactif ionique est de préférence un sel d'un acide carboxylique, notamment d'un acide hydroxycarboxylique, ou un silane cationique ou anionique, ou un oligomère ou un polymère. L'invention concerne en outre un procédé pour produire lesdits revêtements hydrophiles.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE102004001288A DE102004001288A1 (de) | 2004-01-07 | 2004-01-07 | Hydrophile Beschichtung auf Polysilazanbasis |
| PCT/EP2004/014326 WO2005066285A2 (fr) | 2004-01-07 | 2004-12-16 | Revetement hydrophile a base de polysilazane |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP1704193A2 true EP1704193A2 (fr) | 2006-09-27 |
Family
ID=34744635
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP04803939A Withdrawn EP1704193A2 (fr) | 2004-01-07 | 2004-12-16 | Revetement hydrophile a base de polysilazane |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US20070116968A1 (fr) |
| EP (1) | EP1704193A2 (fr) |
| JP (1) | JP2007517943A (fr) |
| KR (1) | KR20060126535A (fr) |
| AR (1) | AR047368A1 (fr) |
| AU (1) | AU2004312142A1 (fr) |
| BR (1) | BRPI0418370A (fr) |
| CA (1) | CA2552733A1 (fr) |
| DE (1) | DE102004001288A1 (fr) |
| NO (1) | NO20063228L (fr) |
| RU (1) | RU2006128576A (fr) |
| TW (1) | TW200528527A (fr) |
| WO (1) | WO2005066285A2 (fr) |
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| DE102004011212A1 (de) * | 2004-03-04 | 2005-09-29 | Clariant International Limited | Perhydropolysilazane enthaltende Beschichtungen für Metall- und Polymeroberflächen |
| DE102004054661A1 (de) * | 2004-11-12 | 2006-05-18 | Clariant International Limited | Verwendung von Polysilazanen zur Beschichtung von Metallbändern |
| DE102005034817A1 (de) * | 2005-07-26 | 2007-02-01 | Clariant International Limited | Verfahren zur Herstellung einer dünnen glasartigen Beschichtung auf Substraten zur Verringerung der Gaspermeation |
| DE102006008308A1 (de) * | 2006-02-23 | 2007-08-30 | Clariant International Limited | Polysilazane enthaltende Beschichtungen zur Vermeidung von Zunderbildung und Korrosion |
| DE102007004570A1 (de) | 2007-01-30 | 2008-07-31 | Daimler Ag | Glänzende Beschichtungen für Aluminium- oder Stahloberflächen und deren Herstellung |
| DE102007052764A1 (de) | 2007-05-04 | 2008-11-06 | Cetelon Lackfabrik Gmbh | Hydrophobe und kratzfeste Lacke für metallische Oberflächen und bremsstaubabweisende Radbeschichtungen |
| DE102007034393A1 (de) | 2007-07-24 | 2009-01-29 | Clariant International Ltd. | Artikel mit geringer Wasserstoffpermeation |
| US8309237B2 (en) * | 2007-08-28 | 2012-11-13 | Alcoa Inc. | Corrosion resistant aluminum alloy substrates and methods of producing the same |
| US7732068B2 (en) * | 2007-08-28 | 2010-06-08 | Alcoa Inc. | Corrosion resistant aluminum alloy substrates and methods of producing the same |
| US20090162544A1 (en) * | 2007-12-20 | 2009-06-25 | Garesche Carl E | Method of surface coating to enhance durability of aesthetics and substrate component fatigue |
| KR101265852B1 (ko) | 2010-01-08 | 2013-05-20 | (주)디엔에프 | 인조대리석용 코팅액 |
| JP2011161302A (ja) * | 2010-02-04 | 2011-08-25 | Konica Minolta Holdings Inc | 塗布方法 |
| DE102011100774A1 (de) | 2010-05-04 | 2011-11-17 | Gmbu E.V., Fachsektion Dresden | Hydrophile Schicht und Verfahren zur Herstellung der Schicht |
| US9533918B2 (en) * | 2011-09-30 | 2017-01-03 | United Technologies Corporation | Method for fabricating ceramic material |
| DE102012014107A1 (de) | 2012-07-17 | 2013-01-24 | Daimler Ag | Beschichtungsverfahren für Oberflächen von Kraftfahrzeugbauteilen |
| US10227160B2 (en) | 2013-09-04 | 2019-03-12 | Owens-Brockway Glass Container Inc. | Polysilazane-derived coating for glass containers |
| US9935246B2 (en) | 2013-12-30 | 2018-04-03 | Cree, Inc. | Silazane-containing materials for light emitting diodes |
| CN105683460B (zh) | 2014-06-20 | 2018-05-22 | 3M创新有限公司 | 孔洞修补装置、套件和方法 |
| KR102808740B1 (ko) | 2014-09-18 | 2025-05-16 | 쓰리엠 이노베이티브 프로퍼티즈 캄파니 | 금속성 표면을 코팅하기 위한 수성 조성물, 방법, 및 물품 |
| SG11201703196WA (en) | 2014-10-24 | 2017-05-30 | Versum Materials Us Llc | Compositions and methods using same for deposition of silicon-containing films |
| EP3430090B1 (fr) | 2016-03-18 | 2020-07-08 | 3M Innovative Properties Company | Compositions contenant un polymère zwittérionique pour le revêtement de surfaces métalliques, procédés et articles |
| CN106519971A (zh) * | 2016-11-22 | 2017-03-22 | 徐煜 | 亲水性硅质镀膜液及镀膜方法 |
| JP2019210370A (ja) * | 2018-06-04 | 2019-12-12 | メルク、パテント、ゲゼルシャフト、ミット、ベシュレンクテル、ハフツングMerck Patent GmbH | ポリシラン骨格を有するブロックとポリシラザン骨格を有するブロックとを含んでなるブロックコポリマー |
| CN108906557B (zh) * | 2018-08-03 | 2021-04-06 | 广州弘海化工科技有限公司 | 一种长效超亲水聚硅氮烷涂层及其制备方法 |
| KR102170244B1 (ko) * | 2019-01-02 | 2020-10-28 | 금오공과대학교 산학협력단 | 마그네슘 합금 표면상의 무기 폴리실라잔 코팅 방법 및 이에 의해 형성된 마그네슘 합금 |
| CN111234288A (zh) * | 2020-01-19 | 2020-06-05 | 东华大学 | 一种亲水性聚合物防雾涂层的制备方法 |
| DE102020207380A1 (de) * | 2020-06-15 | 2021-12-16 | Joysonquin Automotive Systems Gmbh | Verfahren zur herstellung eines dekorteils und durch dieses verfahren herstellbares dekorteil |
| NO348381B1 (en) | 2020-07-02 | 2024-12-23 | Nanize As | Polysilazane coating method and device |
| CN111849347B (zh) * | 2020-08-11 | 2021-11-05 | 中国科学院深圳先进技术研究院 | 一种聚硅氧烷及其应用 |
| CN116814159B (zh) * | 2023-07-20 | 2025-02-07 | 广东金毅科技股份有限公司 | 一种施涂于pp材料的乳液及其制备方法 |
| CN119161618B (zh) * | 2024-09-10 | 2026-02-03 | 中国科学院兰州化学物理研究所 | 一种润滑改性聚合物材料及其制备方法和应用 |
| US20260084183A1 (en) * | 2024-09-20 | 2026-03-26 | WE Group, LLC | Multi-layer coating for stain protection and stain release |
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| JP3307471B2 (ja) * | 1993-02-24 | 2002-07-24 | 東燃ゼネラル石油株式会社 | セラミックコーティング用組成物及びコーティング方法 |
| JP3385060B2 (ja) * | 1993-04-20 | 2003-03-10 | 東燃ゼネラル石油株式会社 | 珪素−窒素−酸素−(炭素)−金属系セラミックス被覆膜の形成方法 |
| JP2000191960A (ja) * | 1998-12-24 | 2000-07-11 | Toto Ltd | 光触媒性親水性コーティング組成物、光触媒性親水性膜の形成方法、及び、光触媒性親水性部材 |
| US6329487B1 (en) * | 1999-11-12 | 2001-12-11 | Kion Corporation | Silazane and/or polysilazane compounds and methods of making |
| US6534184B2 (en) * | 2001-02-26 | 2003-03-18 | Kion Corporation | Polysilazane/polysiloxane block copolymers |
| TWI259844B (en) * | 2001-04-27 | 2006-08-11 | Clariant Int Ltd | Anti-fouling coating solution containing inorganic polysilazane |
| US6652978B2 (en) * | 2001-05-07 | 2003-11-25 | Kion Corporation | Thermally stable, moisture curable polysilazanes and polysiloxazanes |
| US6756469B2 (en) * | 2001-07-18 | 2004-06-29 | Kion Corporation | Polysilazane-modified polyamine hardeners for epoxy resins |
| JP2003170060A (ja) * | 2001-12-10 | 2003-06-17 | Nippon Light Metal Co Ltd | 光触媒機能を有する表面処理製品 |
| US6489499B1 (en) * | 2002-03-11 | 2002-12-03 | United Chemical Technologies, Inc. | Siloxane modified carboxylic acid substituted amines and salts thereof |
| JP4128394B2 (ja) * | 2002-05-16 | 2008-07-30 | クラリアント インターナショナル リミテッド | ポリシラザン含有コーティング膜の親水性促進剤及び親水性維持剤 |
| PL374997A1 (en) * | 2002-11-01 | 2005-11-14 | Clariant International Ltd | Polysilazane-containing coating solution |
-
2004
- 2004-01-07 DE DE102004001288A patent/DE102004001288A1/de not_active Withdrawn
- 2004-12-15 TW TW093138970A patent/TW200528527A/zh unknown
- 2004-12-16 RU RU2006128576/04A patent/RU2006128576A/ru unknown
- 2004-12-16 JP JP2006548149A patent/JP2007517943A/ja active Pending
- 2004-12-16 AU AU2004312142A patent/AU2004312142A1/en not_active Abandoned
- 2004-12-16 KR KR1020067013766A patent/KR20060126535A/ko not_active Withdrawn
- 2004-12-16 CA CA002552733A patent/CA2552733A1/fr not_active Abandoned
- 2004-12-16 BR BRPI0418370-3A patent/BRPI0418370A/pt not_active Application Discontinuation
- 2004-12-16 WO PCT/EP2004/014326 patent/WO2005066285A2/fr not_active Ceased
- 2004-12-16 EP EP04803939A patent/EP1704193A2/fr not_active Withdrawn
- 2004-12-16 US US10/585,392 patent/US20070116968A1/en not_active Abandoned
-
2005
- 2005-01-05 AR ARP050100029A patent/AR047368A1/es unknown
-
2006
- 2006-07-11 NO NO20063228A patent/NO20063228L/no not_active Application Discontinuation
Non-Patent Citations (1)
| Title |
|---|
| See references of WO2005066285A2 * |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2004312142A1 (en) | 2005-07-21 |
| TW200528527A (en) | 2005-09-01 |
| DE102004001288A1 (de) | 2005-08-11 |
| WO2005066285A3 (fr) | 2005-08-18 |
| NO20063228L (no) | 2006-08-09 |
| RU2006128576A (ru) | 2008-02-20 |
| US20070116968A1 (en) | 2007-05-24 |
| WO2005066285A2 (fr) | 2005-07-21 |
| JP2007517943A (ja) | 2007-07-05 |
| AR047368A1 (es) | 2006-01-18 |
| KR20060126535A (ko) | 2006-12-07 |
| CA2552733A1 (fr) | 2005-07-21 |
| BRPI0418370A (pt) | 2007-05-15 |
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