WO2006097206A1 - Hydrophobisation de surface - Google Patents
Hydrophobisation de surface Download PDFInfo
- Publication number
- WO2006097206A1 WO2006097206A1 PCT/EP2006/001970 EP2006001970W WO2006097206A1 WO 2006097206 A1 WO2006097206 A1 WO 2006097206A1 EP 2006001970 W EP2006001970 W EP 2006001970W WO 2006097206 A1 WO2006097206 A1 WO 2006097206A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- silane
- radicals
- glycol
- water
- hydrocarbon
- Prior art date
Links
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title abstract description 20
- 239000005871 repellent Substances 0.000 title abstract description 7
- 230000002940 repellent Effects 0.000 title abstract description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 71
- 238000000034 method Methods 0.000 claims abstract description 23
- 229910000077 silane Inorganic materials 0.000 claims abstract description 22
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract description 18
- 239000000203 mixture Substances 0.000 claims abstract description 18
- 239000004215 Carbon black (E152) Substances 0.000 claims abstract description 16
- 229930195733 hydrocarbon Natural products 0.000 claims abstract description 14
- 239000000758 substrate Substances 0.000 claims abstract description 14
- 150000002334 glycols Chemical class 0.000 claims abstract description 11
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims abstract description 11
- 150000002430 hydrocarbons Chemical class 0.000 claims abstract description 6
- 238000002360 preparation method Methods 0.000 claims description 31
- 150000003961 organosilicon compounds Chemical class 0.000 claims description 16
- 239000002023 wood Substances 0.000 claims description 6
- 239000000123 paper Substances 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000004753 textile Substances 0.000 claims description 3
- 239000006265 aqueous foam Substances 0.000 claims description 2
- 239000000839 emulsion Substances 0.000 claims description 2
- 229910052500 inorganic mineral Inorganic materials 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 239000011707 mineral Substances 0.000 claims description 2
- 150000001875 compounds Chemical class 0.000 abstract 1
- 150000004754 hydrosilicons Chemical class 0.000 abstract 1
- -1 siloxanes Chemical class 0.000 description 39
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
- 230000000694 effects Effects 0.000 description 16
- 239000000047 product Substances 0.000 description 15
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 13
- 230000002209 hydrophobic effect Effects 0.000 description 10
- 238000005470 impregnation Methods 0.000 description 8
- 241000218657 Picea Species 0.000 description 7
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 7
- 238000001035 drying Methods 0.000 description 7
- 229910052710 silicon Inorganic materials 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 239000005055 methyl trichlorosilane Substances 0.000 description 6
- JLUFWMXJHAVVNN-UHFFFAOYSA-N methyltrichlorosilane Chemical compound C[Si](Cl)(Cl)Cl JLUFWMXJHAVVNN-UHFFFAOYSA-N 0.000 description 6
- 239000012071 phase Substances 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 239000004568 cement Substances 0.000 description 5
- 239000004567 concrete Substances 0.000 description 5
- 150000003254 radicals Chemical class 0.000 description 5
- 125000003545 alkoxy group Chemical group 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 239000010703 silicon Substances 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000012190 activator Substances 0.000 description 3
- 229910052910 alkali metal silicate Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- ZTQSADJAYQOCDD-UHFFFAOYSA-N ginsenoside-Rd2 Natural products C1CC(C2(CCC3C(C)(C)C(OC4C(C(O)C(O)C(CO)O4)O)CCC3(C)C2CC2O)C)(C)C2C1C(C)(CCC=C(C)C)OC(C(C(O)C1O)O)OC1COC1OCC(O)C(O)C1O ZTQSADJAYQOCDD-UHFFFAOYSA-N 0.000 description 3
- 239000004571 lime Substances 0.000 description 3
- 150000004756 silanes Chemical class 0.000 description 3
- 239000000126 substance Substances 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000005840 aryl radicals Chemical class 0.000 description 2
- 239000011449 brick Substances 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 239000000460 chlorine Chemical group 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 125000001891 dimethoxy group Chemical group [H]C([H])([H])O* 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000010440 gypsum Substances 0.000 description 2
- 229910052602 gypsum Inorganic materials 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000007791 liquid phase Substances 0.000 description 2
- WCYWZMWISLQXQU-UHFFFAOYSA-N methyl Chemical compound [CH3] WCYWZMWISLQXQU-UHFFFAOYSA-N 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 235000011837 pasties Nutrition 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 230000037452 priming Effects 0.000 description 2
- 238000005096 rolling process Methods 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- SLRMQYXOBQWXCR-UHFFFAOYSA-N 2154-56-5 Chemical compound [CH2]C1=CC=CC=C1 SLRMQYXOBQWXCR-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 235000019738 Limestone Nutrition 0.000 description 1
- QVHMSMOUDQXMRS-UHFFFAOYSA-N PPG n4 Chemical compound CC(O)COC(C)COC(C)COC(C)CO QVHMSMOUDQXMRS-UHFFFAOYSA-N 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N Tetraethylene glycol, Natural products OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 230000004913 activation Effects 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- RMRFFCXPLWYOOY-UHFFFAOYSA-N allyl radical Chemical compound [CH2]C=C RMRFFCXPLWYOOY-UHFFFAOYSA-N 0.000 description 1
- 125000005428 anthryl group Chemical group [H]C1=C([H])C([H])=C2C([H])=C3C(*)=C([H])C([H])=C([H])C3=C([H])C2=C1[H] 0.000 description 1
- 239000003849 aromatic solvent Substances 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011455 calcium-silicate brick Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000002845 discoloration Methods 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 125000003827 glycol group Chemical group 0.000 description 1
- 125000005842 heteroatom Chemical group 0.000 description 1
- 150000002402 hexoses Chemical class 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000002608 ionic liquid Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 238000002955 isolation Methods 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 150000002704 mannoses Chemical class 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- ANLOTXLYXYXJLN-UHFFFAOYSA-N n'-[2-[dimethoxy(methyl)silyl]ethyl]propane-1,3-diamine Chemical compound CO[Si](C)(OC)CCNCCCN ANLOTXLYXYXJLN-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- 229920000620 organic polymer Polymers 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 125000004430 oxygen atom Chemical group O* 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019353 potassium silicate Nutrition 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000002390 rotary evaporation Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000007790 solid phase Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000004528 spin coating Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000005728 strengthening Methods 0.000 description 1
- 235000000346 sugar Nutrition 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- GPHYWIXZJBGHPO-UHFFFAOYSA-N trichloro(6-methylheptyl)silane Chemical compound CC(C)CCCCC[Si](Cl)(Cl)Cl GPHYWIXZJBGHPO-UHFFFAOYSA-N 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000012855 volatile organic compound Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
- C04B41/49—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes
- C04B41/4905—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon
- C04B41/495—Compounds having one or more carbon-to-metal or carbon-to-silicon linkages ; Organo-clay compounds; Organo-silicates, i.e. ortho- or polysilicic acid esters ; Organo-phosphorus compounds; Organo-inorganic complexes containing silicon applied to the substrate as oligomers or polymers
- C04B41/4961—Polyorganosiloxanes, i.e. polymers with a Si-O-Si-O-chain; "silicones"
-
- C—CHEMISTRY; METALLURGY
- C04—CEMENTS; CONCRETE; ARTIFICIAL STONE; CERAMICS; REFRACTORIES
- C04B—LIME, MAGNESIA; SLAG; CEMENTS; COMPOSITIONS THEREOF, e.g. MORTARS, CONCRETE OR LIKE BUILDING MATERIALS; ARTIFICIAL STONE; CERAMICS; REFRACTORIES; TREATMENT OF NATURAL STONE
- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/009—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone characterised by the material treated
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
- C08G77/18—Polysiloxanes containing silicon bound to oxygen-containing groups to alkoxy or aryloxy groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M23/00—Treatment of fibres, threads, yarns, fabrics or fibrous goods made from such materials, characterised by the process
- D06M23/04—Processes in which the treating agent is applied in the form of a foam
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
Definitions
- the invention relates to a process for the hydrophobization of substrates with glycole-functional organosilicon compounds.
- WO 95/25706 describes a process for hydrophobing with solvent-free, bentonite-thickened silane / siloxane mixtures.
- Hydrogen-containing organosiloxane and alkali metal silicate preferably at high drying temperatures.
- US 2,887,467 A describes the synthesis of water-soluble silsesquioxanes by reacting non-water-soluble silsesquioxanes with ethylene glycol at temperatures of about 150 0 C, wherein each silicon atom at least 3 equivalents of ethylene glycol must be present.
- the products thus obtained are basically suitable for use as water repellents.
- Products are water-soluble hydrophobic impregnating agents. They are characterized by the fact that they are at least three times more polar Substituents per silicon atom is required to obtain a suitable hydrophobizing agent. Hydrophobic does not affect the polar group, but the silicon-based portion. Due to the high proportion of polar substituents that have to be eliminated for good hydrophobing at least to the extent that a no longer water-soluble hydrophobizing product is formed, high amounts of water repellents must be dosed in order to obtain a good efficiency. The removal of the polar groups requires the adjustment of suitable reaction conditions for the hydrolysis and condensation, which limits the usability of these products. On essentially neutral substrates such as bricks, paper, wood and textiles, these products have no hydrophobic effect.
- the invention relates to a process for the hydrophobization of substrates with organosilicon compounds O, which can be prepared by reacting a molar equivalent of silane S, which is selected from
- the hydrocarbon radicals of the silane S are preferably C 1 -C 2 -5-hydrocarbon radicals.
- Examples of the C 1 -C 4 -carbon radicals are alkyl radicals, such as the methyl, ethyl, n-propyl, iso-propyl, n-butyl, iso-butyl, tert. Butyl, n-pentyl, iso-pentyl, neo-pentyl, tert.
- Hexylres- te such as the n-hexyl radical
- Heptyl radicals such as the n-heptyl radical
- Octyl radicals such as the n-octyl radical and iso-octyl radicals, such as
- - nonyl radicals such as the n-nonyl radical
- Decyl radicals such as the n-decyl radical
- Dodecyl radicals such as the n-dodecyl radical
- Alkenyl radicals such as the vinyl and the allyl radical / cycloalkyl radicals, such as cyclopentyl, cyclohexyl, cycloheptyl radicals and methylcyclohexyl radicals
- Aryl radicals such as the phenyl
- alkaryl radicals such as o-, m-, p-tolyl radicals
- Xylyl radicals and ethylphenyl radicals Aralkylres- te, such as the benzyl radical, the alpha- and the 3-phenylethyl radical.
- halogen-substituted C 1 -C 4 -hydrocarbon radicals are substituted by fluorine, chlorine, bromine and iodine atoms.
- ⁇ J te alkyl radicals such as 3, 3, 3-trifluoro-n-propyl, 2,2,2,2 ', 2', 2 '-Hexafluorisopropylrest, the Heptafluoriso- propyl radical, and haloaryl radicals such as the o-, m- and p-chlorophenyl.
- Particularly preferred are the non-substituted C 1 -C 8 -alkyl radicals, in particular the methyl radical and the ethyl radical.
- the Kohlenwasserstoffoxyreste the silane S 5 C] _ Ci5 hydrocarbon radicals.
- Hydrocarbonoxy radicals are the above C 1 -C 15 hydrocarbon radicals which are bonded to the silicon atom via a divalent oxygen atom. Particularly preferred are the unsubstituted C 1 -C 3 -alkyl radicals,
- the halo radicals of the silane S are chlorine radicals.
- the silane S may still contain small amounts, preferably at most 5 15 mol%, in particular at most 2 mol% of silanes selected from dihydrocarbyl dihalosilane, trihydrocarbylsilane, tetrahalosilane, dihydrocarbyldikohlenwasserstoffox- silane, Trikohlenwasserstoff-kohlenwassersto ' ffoxy-silane and 20 Tetrakohlenwasserstoffoxy-silam
- the glycol G is preferably a linear or branched monomeric or oligomeric C2 -Cg glycol, and mixed glycols, in particular C2-C4 glycol having a total of at most 40 25 carbon atoms, preferably at most 25, in particular at most 15 carbon atoms.
- ethylene glycol or its oligomers but also propylene glycol or its oligomers and i () mixed glycols with propylene glycol and ethylene glycol units.
- the oligomers have at most 6, in particular at most 3 monomer units.
- silicone resin networks are formed in the application on the substrate, which lead to the pronounced hydrophobicity.
- glycol-functional organosilicon compounds O which are used for the process according to the invention are silanes, oils or resins or a mixture of both, wherein they are composed of units of the general formula 1,
- R is a monovalent, optionally halogen-substituted C 1 -
- Hydrocarbonoxy or hydroxyl groups a is 1, b is 0, 1, 2 or 3 and on average over the entire
- Molecule has a minimum value of 0.1
- G is a hydroxy radical or a monovalent or bivalent branched or linear C2-C25 glycol residue.
- radicals R are Kohlenwasserstoffoxyreste.
- branched or linear C 2 -C 25 -glycol radicals are alpha-omega hydroxy-functional glycols, such as ethylene glycol,
- C] _-Ci_5-hydrocarbon radical and hydrocarbonoxy radicals R are the radicals described above for the silane S.
- the organosilicon compounds O can be used either as a pure substance for hydrophobization, or they are used in preparations together with other components.
- the preparations are aqueous solutions comprising at least one organosilicon compound O and water.
- Such preparations may also contain the commonly used water repellents, such as the silanes, siloxanes and silicates reproduced in the publications cited above, and also, if appropriate, additional emulsifiers.
- Aqueous, non-aqueous or solvent-based preparations are obtained by adding the
- Organosilicon compounds O combined with other ingredients, which combinations do not necessarily give homogeneous mixtures.
- Possible components which can be used to prepare preparations for carrying out the method according to the invention are, for example
- Alkoxy and aryloxysilanes which may additionally have organofunctional radicals or alkyl or aryl radicals, and also the hydrolysates and condensates obtainable therefrom, and also mixtures thereof,
- Silicone resins one or more organic solvents, such as aromatic solvents, ketones, esters, alcohols, aliphatic and cycloaliphatic solvents, ionic liquids and glycols,
- organic polymers such as polyvinyl alcohol, polyvinyl acetate, polyacrylates, styrene acrylate copolymers, polyvinyl butyrals, polyurethanes and polyepoxides,
- the components to be mixed can be processed into a homogeneous, uniform active substance mixture. If necessary, you can multiphase mixtures of several liquid phases or of solid and liquid phases are formed, wherein the consistency of the products obtained may be both low viscosity liquid and pasty or creamy or also powdery solid.
- the formulations are liquid or pasty and are distributed by conventional methods of distribution on the surface of the substrate, such as by brushing, spraying, lolling, rolling, pouring, filling, dipping, spincoating and rolling.
- the hydrophobing of the substrates comprises the priming and impregnation.
- the preparations themselves contain a basic activator.
- a basic activator is recommended for the rapid formation of hydrophobicity.
- the basic component can be incorporated into the preparation itself, wherein it is optionally masked in the preparation in such a way that it is released only in the later application, or it is readily used in the preparation, if thereby the usability of the preparation is not restricted. If appropriate, the basic component can also first be applied to the substrate in a separate step, followed by the preparation containing the organosilicon compounds O first.
- the order can also be reversed, that is, first the preparation is applied to the organosilicon compound O on the substrate and then the basic component.
- the basic component can be applied as a pure substance or as a preparation.
- the basic component itself does not have a hydrophobing effect have. It is needed only in catalytic amounts. Typical amounts of basic activation activator are in the range of 0.01-5.0 weight percent, based on the weight of organosilicon compound O used, and are selected depending on how quickly the hydrophobicity is desired or how strong the catalytic effect of each component is is.
- the preparations are preferably used as aqueous preparation, as emulsion or as aqueous foam.
- Surfactants can be used to prepare aqueous preparations or they can be prepared without the addition of surfactants by introducing the organosilicon compounds O directly into water.
- the preparation of aqueous preparations without the use of surfactants is possible in particular when the organosilicon compounds O are self-emulsifying or water-soluble in water.
- Example Ia Condensation product of methyltrichlorosilane and ethylene glycol, preparation of organosilicon compounds 0:
- Apparatus 2 l three-necked flask with intensive cooler, dropping funnel and paddle stirrer. The gas discharge and the application of vacuum via the intensive cooler.
- Methyltrichlorosilane is mixed with toluene in a ratio of 1: 1 and metered into a receiver of 2.8 times the molar excess of ethylene glycol by means of a dropping funnel.
- a gentle water-jet vacuum is constantly applied to the apparatus (about 200 mbar).
- a mixture of 473.10 g of methyltrichlorosilane and 473.10 g of toluene is introduced into the dropping funnel.
- the mixture of methyltrichlorosilane and toluene is metered from the dropping funnel below the surface of the ethylene glycol reservoir.
- the temperature is maintained over the dosing between 50 0 C and 55 0 C.
- the duration of the dosage is about 70 minutes.
- the system is refluxed for 2 hours. After this. Refluxing the batch is cooled to room temperature.
- phase is toluene and the second phase being the product phase containing the polyether-modified polysiloxane.
- the HCl content of the crude product is ⁇ 50 ppm.
- the phases are separated and from the product phase, the toluene is removed by rotary evaporation under vacuum (about 10 mbar, 110 0 C distilled off.
- a 10% strength aqueous solution is prepared by adding water. The solution is clear.
- aqueous solution of the glycol-functional siloxane according to Example Ib is 0.5 percent by weight based on the amount of glycol siloxane of a 30% aqueous solution of
- Methyl (dimethoxy) (aminopropylaminoethyl) silane is Methyl (dimethoxy) (aminopropylaminoethyl) silane.
- Example Ia isooctyltrichlorosilane is reacted with ethylene glycol instead of methyltrichlorosilane.
- the stoichiometry is set exactly the same as described for Example Ia.
- the reaction and product isolation likewise take place exactly as indicated in Example Ia.
- Example 2 Hydrophobic impregnation of a fiber cement board:
- Example 3 Hydrophobic impregnation of a
- Example 3 Hydrophobic Impregnation of Concrete Cylinders: In the preparations according to Examples Ia, Ib and Id, small concrete cylinders produced from a commercial concrete (w / c value 0.35-0.6) are immersed in accordance with the manufacturer's instructions. After 1 day of drying at room temperature, water is added dropwise to the concrete body treated in this way and the wetting behavior is qualitatively assessed: Ia: very good beading effect Ib: very good beading effect Id: very good beading effect
- EXAMPLE 5 10.0 g of a 1% aqueous solution of a methyl (dimethoxy) (aminopropylamioethyl) silane are brushed evenly on spruce boards (10 ⁇ 15 cm) with a brush. Thereafter, the preparations Ia and Ib in an amount of 500 g / m 2 are uniformly painted over. After drying for 1 day at room temperature, water is added dropwise to the spruce boards treated in this way and the wetting behavior is assessed qualitatively: Ia: very good beading effect Ib: very good beading effect
- Example 6 500 g / m 2 of the preparations Ia and Ib are evenly spread on spruce boards (10 ⁇ 15 cm) with a brush. Thereafter, in each case 10.0 g of a 1% aqueous solution of
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Ceramic Engineering (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Silicon Polymers (AREA)
Abstract
La présente invention concerne un procédé pour hydrophobiser des substrats comprenant des composés d'organosilicium O qui peuvent être produits en mettant en réaction un équivalent molaire de silane S choisi parmi du trihalogénosilane d'hydrocarbure, du trihydrocarbure-oxysilane d'hydrocarbure ou des mélanges de ceux-ci avec de 2,0 à 2,99 équivalents molaires d'un glycol G ou d'un mélange de glycols G.
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE200510012411 DE102005012411A1 (de) | 2005-03-17 | 2005-03-17 | Oberflächenhydrophobierung |
DE102005012411.9 | 2005-03-17 |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006097206A1 true WO2006097206A1 (fr) | 2006-09-21 |
Family
ID=36215752
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/EP2006/001970 WO2006097206A1 (fr) | 2005-03-17 | 2006-03-03 | Hydrophobisation de surface |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE102005012411A1 (fr) |
WO (1) | WO2006097206A1 (fr) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101100821B (zh) * | 2007-07-04 | 2010-05-26 | 中国科学院长春应用化学研究所 | 超疏水棉纤维材料或超疏水纸纤维材料的制备方法及用途 |
DE102011084301A1 (de) | 2011-10-11 | 2013-04-11 | Wacker Chemie Ag | Verfahren zur Massehydrophobierung von Baustoffen mit festen Organosiliciumverbindungen |
WO2022128994A1 (fr) | 2020-12-18 | 2022-06-23 | Evonik Operations Gmbh | Compositions aqueuses stables à la dilution pour l'hydrophobisation en masse de matériaux de construction minéraux |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE102015102382A1 (de) * | 2015-02-19 | 2016-08-25 | Bundesrepublik Deutschland, Vertreten Durch Den Bundesminister Für Wirtschaft Und Energie, Dieser Vertreten Durch Den Präsidenten Der Bundesanstalt Für Materialforschung Und -Prüfung (Bam) | Verfahren zur dauerhaften Hydrophobierung und/oder Superhydrophobierung von Betonoberflächen |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2906768A (en) * | 1957-12-05 | 1959-09-29 | Dow Corning | Method of reacting halosilanes with diols |
DE1076946B (de) * | 1956-04-30 | 1960-03-03 | Gen Electric | Verfahren zur Herstellung von zur Hydrophobierung und Appretierung geeigneten Organopolysiloxane |
-
2005
- 2005-03-17 DE DE200510012411 patent/DE102005012411A1/de not_active Withdrawn
-
2006
- 2006-03-03 WO PCT/EP2006/001970 patent/WO2006097206A1/fr not_active Application Discontinuation
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE1076946B (de) * | 1956-04-30 | 1960-03-03 | Gen Electric | Verfahren zur Herstellung von zur Hydrophobierung und Appretierung geeigneten Organopolysiloxane |
US2906768A (en) * | 1957-12-05 | 1959-09-29 | Dow Corning | Method of reacting halosilanes with diols |
Cited By (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101100821B (zh) * | 2007-07-04 | 2010-05-26 | 中国科学院长春应用化学研究所 | 超疏水棉纤维材料或超疏水纸纤维材料的制备方法及用途 |
DE102011084301A1 (de) | 2011-10-11 | 2013-04-11 | Wacker Chemie Ag | Verfahren zur Massehydrophobierung von Baustoffen mit festen Organosiliciumverbindungen |
WO2013053609A1 (fr) | 2011-10-11 | 2013-04-18 | Wacker Chemie Ag | Procédé d'hydrofugation dans la masse de matériaux de construction au moyen de composés d'organosilicium solides |
WO2022128994A1 (fr) | 2020-12-18 | 2022-06-23 | Evonik Operations Gmbh | Compositions aqueuses stables à la dilution pour l'hydrophobisation en masse de matériaux de construction minéraux |
Also Published As
Publication number | Publication date |
---|---|
DE102005012411A1 (de) | 2006-09-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
EP1154971B1 (fr) | Creme aqueuse a base de composes organosiliciques | |
EP0919526B1 (fr) | Matériaux de construction comprenant des poudres contenant des composés d'organosilice hydrophobiques | |
EP0819665B1 (fr) | Crèmes aqueuses en composés organosiliciés pour rendre hydrophobe des matériaux de construction | |
DE60121164T2 (de) | Wasserabweisende Organosilikonzusammensetzung | |
EP0242798B1 (fr) | Emulsions aqueuses de polysiolxane et leur emploi | |
DE4029640C2 (fr) | ||
EP1205481B1 (fr) | N-Propyléthoxysiloxane, sa préparation et son utilisation | |
EP1674436A1 (fr) | Mélange de siloxanes fonctionnalisés par des glycoles. | |
EP1983019A2 (fr) | Siloxanes modifiés organiquement et leur utilisation pour la fabrication de préparations pour imprégnations hydrofuges | |
EP0908498A2 (fr) | Emulsions d'organosilicon pour rendre hydrophobe des matériaux de construction | |
EP2766319B1 (fr) | Procédé d'hydrofugation dans la masse de matériaux de construction au moyen de composés d'organosilicium solides | |
DE102008063965A1 (de) | Hydrophobierte zementhaltige Zusammensetzungen | |
DE102011086362A1 (de) | Zusammensetzung umfassend Block-Co-Kondensate von Propyl-funktionellen Alkali-Siliconaten und Silicaten sowie Verfahren zu deren Herstellung | |
EP3433321B1 (fr) | Masses réticulables à base de composés organosiliciés | |
WO2006097206A1 (fr) | Hydrophobisation de surface | |
EP0791566B1 (fr) | Revêtement auto-apprêtant pour matériaux de construction | |
US9528036B2 (en) | Low-voc dialkyl-functional alkoxysiloxanes, processes and use thereof as hydrophobizing impregnating agents for mineral building materials | |
DE2330887A1 (de) | Verwendung von alkyl/aryl-alkoxypolysiloxanen zur impraegnierung | |
EP2516509B1 (fr) | Résines de silicone dispersibles dans l'eau | |
EP1331239B1 (fr) | Crème eau dans l'huile à base de composés organosiliciques | |
DE10203247A1 (de) | Wasser-in-Öl-Cremes von Organo-Siliciumverbindungen | |
DE102005046704A1 (de) | Hydrophobierung von Substraten mit phosphonatofunktionellen Siloxanen | |
WO2020108762A1 (fr) | Procédé d'hydrofugation de matériau léger minéral | |
WO2008113764A1 (fr) | Peintures aqueuses |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
NENP | Non-entry into the national phase |
Ref country code: RU |
|
WWW | Wipo information: withdrawn in national office |
Country of ref document: RU |
|
122 | Ep: pct application non-entry in european phase |
Ref document number: 06707402 Country of ref document: EP Kind code of ref document: A1 |
|
WWW | Wipo information: withdrawn in national office |
Ref document number: 6707402 Country of ref document: EP |